N-CSRS 1 windsorfundsncsrs.htm N-CSR FORM FOR WINDSOR FUNDS

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

FORM N-CSR

CERTIFIED SHAREHOLDER REPORT
OF
REGISTERED MANAGEMENT COMPANY


Investment Company Act file number: 811-834

Name of Registrant: Vanguard Windsor Funds

Address of Registrant: P.O. Box 2600
Valley Forge, PA 19482

Name and address of agent for service: R. Gregory Barton, Esquire
P.O. Box 876
Valley Forge, PA 19482

Registrant’s telephone number, including area code: (610) 669-1000


Date of fiscal year end: October 31

Date of reporting period: November 1, 2004 – April 30, 2005

Item 1: Reports to Shareholders




Vanguard® Windsor™ Fund

April 30, 2005





CONTENTS
  1   CHAIRMAN'S LETTER
  6   ADVISOR'S REPORT
  9   FUND PROFILE
10  GLOSSARY OF INVESTMENT TERMS
11  PERFORMANCE SUMMARY
12  FINANCIAL STATEMENTS
23  ABOUT YOUR FUND'S EXPENSES
24  ADVANTAGES OF VANGUARD.COM

SUMMARY

• During the six months ended April 30, 2005, Vanguard Windsor Fund returned 5.0% for both of its share classes.
• U.S. stocks rallied in the final months of 2004, then drifted lower as concerns about the strength and durability of the expansion took hold.
• Windsor’s investments in health care and financial services stocks accounted for a large portion of the fund’s returns.

VANGUARD’S PLEDGE TO CLIENTS

We recognize that your relationship with Vanguard rests on the twin pillars of trust and excellence, each of which is built upon the character of our people. Our Pledge to Clients reflects our ongoing efforts to deserve your trust and to continually improve so that we can offer you excellence in all that we do. We will:

• Put your interests first at all times.

• Continually seek to earn your trust by adhering to the highest standards of ethical behavior and fiduciary responsibility.

• Strive to be the highest-value provider of investment services, which means outstanding investment performance and service, both at the lowest possible cost.

• Communicate candidly not only about the rewards of investing but also about the risks and costs.

• Maintain highly effective controls to safeguard your assets and protect your confidential information.

• Invest a majority of our personal assets alongside yours.


Please note: The opinions expressed in this report are just that—informed opinions. They should not be considered promises or advice. Also, please keep in mind that the information and opinions cover the period through the date on the cover of this report. Of course, the risks of investing in your fund are spelled out in the prospectus.


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CHAIRMAN’S LETTER



Dear Shareholder,

Vanguard Windsor Fund produced a return of 5.0% for both of its share classes during the first half of its 2005 fiscal year. The gain put it ahead of the broad market, in line with comparable funds, and behind the Russell 1000 Value Index.

The table below presents the six-month total returns (capital change plus reinvested distributions) for the fund, its average peer, and two index benchmarks. Your fund’s starting and ending net asset values, plus income distributions, appear on page 5.

Windsor’s most significant gains came in the health care sector, where the fund has been buying stocks that have fallen out of favor with investors. The fund has also been acquiring beaten-down technology stocks; however, on balance, these hurt performance during the half-year.


Total Returns
 

Six Months Ended
April 30, 2005

Vanguard Windsor Fund  
 Investor Shares 5.0%
 Admiral Shares 5.0   
Russell 1000 Value Index 6.7   
Average Multi-Cap Value Fund* 5.2   
Dow Jones Wilshire 5000 Index 3.5   

*Derived from data provided by Lipper Inc.

AS 2005 OPENED, STOCKS STALLED AMID UNCERTAINTY

U.S. stocks rallied in the final months of 2004, then drifted lower as the New Year began. Although the economy registered respectable growth during the fiscal half-year, concern about the strength and durability of the expansion seemed to dictate the market’s direction. Segments of corporate America generated unexpectedly robust profits, for example, but every instance of good news seemed to be overshadowed by a high-profile disappointment. Persistently high oil prices and other specters of inflation also cast a pall on the market’s mood.

The broad stock market, as measured by the Dow Jones Wilshire 5000 Composite Index, returned 3.5% for the six months. As has been the case for much of the past five years, value-oriented stocks outpaced

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Admiral™ Shares

A lower-cost class of shares available to many longtime shareholders and to those with significant investments in the fund.


their growth-oriented counterparts. In a reversal of recent trends, large-capitalization stocks bested the market’s smaller companies. On balance, international stocks generated higher returns than the U.S. market.

THE FED STEPPED TO THE FORE

In the bond market, the Federal Reserve Board commanded the spotlight, signaling that its near-term objective was to short-circuit any surge in inflation. The Fed raised its target for the federal funds rate to 2.75% during the half-year, a full percentage point higher than its level at the start of the period. (In early May, the Fed raised its target to 3.00%.) The yield of the 3-month U.S. Treasury bill paralleled the Fed’s actions, increasing steadily to close the period at 2.89%.

The impact on longer-term securities was less pronounced. The yield of the benchmark 10-year Treasury note rose 0.18 percentage point to 4.20%, while the yields of the longest-term securities declined modestly.

THE ENVIRONMENT WAS FAVORABLE TO VALUE INVESTORS

Windsor Fund offers investors a chance to own stocks that are—at least temporarily—under a cloud. While some see only the downside, the fund’s managers see opportunity in companies facing unfavorable media attention, guilt by association with a fallen peer, or the uncertainty of a management change. The stock market has been retreating for much of 2005, providing plenty of opportunity to find overly punished stocks.


Market Barometer
 
Total Returns
Periods Ended April 30, 2005

 
 
 
 
Six
Months
One
Year
Five
Years*

  Russell 1000 Index (Large-caps) 4.0% 7.2% -2.7%
  Russell 2000 Index (Small-caps) -0.1    4.7    4.1   
  Dow Jones Wilshire 5000 Index 3.5    7.0    -2.0   
Stocks    (Entire market)      
  MSCI All Country World Index      
     ex USA (International) 9.1    16.9    0.6   

  Lehman Aggregate Bond Index 1.0% 5.3% 7.5%
     (Broad taxable market)      
Bonds Lehman Municipal Bond Index 1.9    6.8    7.0   
  Citigroup 3-Month Treasury Bill Index 1.1    1.7    2.6   

CPI Consumer Price Index 1.9% 3.5% 2.6%

*Annualized

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The fund enjoyed its greatest success with health care stocks, five of which were among the top ten contributors to overall performance during the six months. WellPoint, the fund's best-performing stock, is the United States' largest health insurer and has been taking market share from other health maintenance organizations. The other top-performing health stocks included Health Net, also a managed health company, and pharmaceutical companies Sanofi-Aventis, Wyeth, and GlaxoSmithKline.


Fund Assets Managed April 30, 2005
 
$ Million
Percentage
Wellington Management Company, LLP $14,009  70%
Sanford C. Bernstein & Co., LLC 5,668  28   
Cash Investments* 397  2   

Total $20,074  100%

*These short-term reserves are invested by Vanguard in equity index products to simulate investment in stocks. Each advisor may also maintain a modest cash position.

Slightly more than one-quarter of fund assets are in financial services firms. During the first half of the fiscal year, these stocks provided modest gains as a group, though there were pockets of notable strength, including top holding Citigroup.

On the other hand, the fund’s technology stocks, on balance, detracted from performance. Technology is a notoriously volatile sector, requiring extra patience from its investors.

The fund has historically earned strong returns from companies that produce or process raw materials. In the fiscal half-year, however, this exposure hurt the overall return. Top-ten holding Alcoa, the world’s largest aluminum maker, fell –10%, and Smurfit-Stone Container, which makes corrugated cardboard containers, dropped –24%.


Annualized Expense Ratios:
Your fund compared with its peer group
 
 
 

 
Investor
Shares

 
Admiral
Shares

Average
Multi-Cap
Value Fund

Windsor Fund 0.37% 0.26% 1.42%*

*Peer-group expense ratio is derived from data provided by Lipper Inc. and captures information through year-end 2004.

The portfolio is built by two investment advisors with different approaches to value investing. Wellington Management Company and Sanford C. Bernstein & Co. independently manage portions of Windsor Fund’s assets, as shown in the table above. Having two advisors enhances portfolio diversifica-tion while preserving one of the most important benefits of active management—namely, the potential to outperform the broad market.

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THE FUND’S INVESTMENT STYLE DEMANDS A LONG-TERM VIEW

Windsor’s hallmark is taking large positions in stocks that are unloved and holding them until they regain favor. Some stocks will bounce back quickly; some face a long, slow climb back to a more reasonable valuation; and occasionally a stock will not recover. To benefit from this approach, investors need to think long-term. Just as a ship doesn’t turn on a dime, neither does a corporation facing complex challenges, even if they are temporary ones.

Value stocks have outperformed growth stocks during most of the past five years. For some contrarian investors, this is a signal to shift to growth stocks. Others look at strong five-year gains for value stocks and are tempted to shift more money into these stocks. Neither approach is sound. Such moves undermine the benefits of a long-term diversified approach precisely because no one can predict when and to what degree markets will shift.

Building a portfolio of well-diversified stock, bond, and money market mutual funds in alignment with your unique financial circumstances remains the best advice we offer. Make the most of this approach by keeping an eye on costs. Vanguard Windsor Fund offers a low-cost plank to help you build such an investment platform.

Thank you for entrusting your assets to us.

Sincerely,

John J. Brennan

CHAIRMAN AND CHIEF EXECUTIVE OFFICER

MAY 11, 2005




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Your Fund's Performance at a Glance October 31, 2004-April 30, 2005
 
  Distributions Per Share
 
 

Starting
Share Price

Ending
Share Price

Income
Dividends

Capital
Gains

Windsor Fund        
   Investor Shares $16.75  $17.35  $0.150  $0.088 
   Admiral Shares 56.56  58.58  0.537  0.297 




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ADVISOR’S REPORT

We are pleased that Vanguard Windsor Fund’s return of 5.0% for the first half of the 2005 fiscal year was solidly ahead of the 3.3% gain of the Standard & Poor’s 500 Index, even though the fund return was simply in line with the 5.2% return of the average multi-cap value fund. The fund lagged the 6.7% return of the Russell 1000 Value Index, which includes large- and mid-capitalization value stocks. (Please note that the following comments concern the 70% of fund assets managed by Wellington Management Company as of April 30.)

Our positive performance compared with the S&P 500 Index was driven predominantly by the very strong contribution of our pharmaceutical and HMO holdings within the health care sector, including WellPoint, Sanofi-Aventis, Health Net, Wyeth, and GlaxoSmithKline. The fund also benefited from solid contributions from Petrol Brasil (integrated oils), Citigroup (banking), Hartford Financial Services (insurance), KB Home (homebuilding), Comcast (cable television), Michelin (tires), and Freescale Semiconductor (technology).


Investment Philosophy

The fund reflects a belief that superior long-term investment results can be achieved by emphasizing common stocks that are generally misunderstood, out of favor, or undervalued by fundamental measures such as price/earnings ratio or dividend yield. The fund may concentrate a large portion of assets in those securities or industries the advisors believe offer the best return potential.


Partially offsetting the successes noted above were a few meaningful underperformers. Topping this list was Fannie Mae, where negative factors aligned to put the future value of a once-great franchise at risk. Our investment style incorporates taking sizable positions in the fund when we find an attractive valuation and have strong conviction. If our conviction is broken, as in the case of Fannie Mae, we reduce our position and move on to greener pastures, despite our emotional difficulty in selling a stock that has badly underperformed.

Other poor performers—although we are staying the course for these—included semiconductor equipment stocks, particularly Applied Materials and Teradyne. These stocks have continued to underperform despite underlying fundamentals that are playing out consistently with our expectations.




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Finally, our investments in Alcoa and Smurfit-Stone Container within the materials & processing sector also detracted from fund performance.

Numerous value indexes have had very strong performance relative to growth indexes since the Internet bubble burst in early 2000. This outperformance has continued over the past year, as many traditional growth investors have jumped fences to bid up cyclical stocks of energy, industrial, and materials companies. The valuation level of these stocks now incorporates a tremendous amount of optimism and hope that “this time it’s different.” While we are diehard value investors, we view our investment universe as the broad market, not just the stocks that populate the numerous value indexes. In these times of high prices for traditional value stocks, we have been finding more compelling investment value in such traditional growth stocks as Cisco Systems, Sanofi-Aventis, GlaxoSmithKline, Nextel Communications, and Microsoft.

Not fully participating in the enthusiasm over cyclical stocks has hurt the fund’s performance relative to the Russell 1000 Value Index over the past year or so, but we remain steadfast in our commitment to invest only where we see solid value and to position the portfolio for the period when investors realize that this time it’s not different.

Our investment philosophy is predicated on the belief that markets are efficient over the long term but that, in the short and intermediate terms, they tend to exaggerate current trends and overreact to new information. This is even truer today with the explosive growth of hedge funds, which tend to have very short time horizons. We focus on trying to assess the fair value of a company when viewed in a long-term context, and we seek to opportunistically take advantage of price dislocations that result from the market’s shorter-term focus. In most cases, we demand the potential for at least 30% price appreciation to reach our estimate of fair value before we will consider a stock for purchase in the fund. Because we are by nature contrarians, with a longer investment horizon than most others in the market possess, the fund’s investment results can differ meaningfully from those of broad-market or value-style indexes in any given quarter or year; however, over the longer term we strive to outperform both.

While economic growth has moderated due to higher short-term interest rates and energy prices, we remain reasonably positive about the outlook for the economy over the next year. Nonetheless, decelerating economic




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growth creates uncertainty, increases investor concerns regarding company earnings, and contributes to short-term volatility in stocks. We suspect this will generate at least a temporary movement by investors to reduce risk in their portfolios.

We remain enthusiastic about the value in the fund today, and we will continue to toil diligently in search of meaningfully undervalued stocks in an effort to reward our shareholders for their trust and patience in the years ahead.

David R. Fassnacht, PORTFOLIO MANAGER

WELLINGTON MANAGEMENT COMPANY, LLP

MAY 17, 2005




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As of 4/30/2005

FUND PROFILE

This Profile provides a snapshot of the fund’s characteristics, compared where indicated with both an appropriate market index and a broad market index. Key terms are defined on page 10.

WINDSOR FUND
Portfolio Characteristics
 
 

 
Fund

Comparative
Index*

Broad
Index**

Number of Stocks 149  695  4,949 
Median Market Cap $37.6B  $32.7B  $26.4B 
Price/Earnings Ratio 16.2x  15.8x  21.2x 
Price/Book Ratio 2.2x  2.2x  2.6x 
Yield 2.5% 1.7%
  Investor Shares 1.3%
  Admiral Shares 1.4%
Return on Equity 17.7% 17.3% 15.0%
Earnings Growth Rate 8.3% 9.3% 9.0%
Foreign Holdings 13.0% 0.0% 1.0%
Turnover Rate 36%†  —  — 
Expense Ratio —  — 
  Investor Shares 0.37%†       
  Admiral Shares 0.26%†       
Short-Term Reserves 2% —  — 




Volatility Measures
 
 

 
Fund

Comparative
Index*

 
Fund

Broad
Index**

R-Squared 0.97  1.00  0.98  1.00 
Beta 1.12  1.00  1.15  1.00 




Sector Diversification (% of portfolio)
 
 

 
Fund

Comparative
Index*

Broad
Index**

Auto & Transportation 5% 2% 2%
Consumer Discretionary 9    9    16   
Consumer Staples 2    6    7   
Financial Services 26    32    23   
Health Care 13    4    13   
Integrated Oils 6    10    4   
Other Energy 1    3    3   
Materials & Processing 5    5    4   
Producer Durables 5    4    5   
Technology 11    5    12   
Utilities 9    13    7   
Other 6    7    4   

Short-Term Reserves 2%

  *Russell 1000 Value Index.
**Dow Jones Wilshire 5000 Index.
†Annualized.



Ten Largest Holdings (% of total net assets)
 
Citigroup, Inc. 5.3%
  (banking)
Comcast Corp. 3.8   
  (telecommunications)
Bank of America Corp. 3.7   
  (banking)
Tyco International Ltd. 3.0   
  (conglomerate)
Wyeth 2.9   
  (pharmaceuticals)
Cisco Systems, Inc. 2.7   
  (computer hardware)
Alcoa Inc. 2.4   
  (metals and mining)
Microsoft Corp. 2.4   
  (computer software)
Sanofi-Synthelabo SA ADR 2.3   
  (pharmaceuticals)
Applied Materials, Inc. 2.3   
  (electronics)

Top Ten 30.8%

“Ten Largest Holdings” excludes any temporary cash investments and equity index products.



Investment Focus

    Visit our website at Vanguard.com
for regularly updated fund information.



9




GLOSSARY OF INVESTMENT TERMS

Beta. A measure of the magnitude of a fund’s past share-price fluctuations in relation to the ups and downs of a given market index. The index is assigned a beta of 1.00. Compared with a given index, a fund with a beta of 1.20 typically would have seen its share price rise or fall by 12% when the index rose or fell by 10%. A fund’s beta should be reviewed in conjunction with its R-squared (see definition below). The lower the R-squared, the less correlation there is between the fund and the index, and the less reliable beta is as an indicator of volatility.


Earnings Growth Rate. The average annual rate of growth in earnings over the past five years for the stocks now in a fund.


Expense Ratio. The percentage of a fund’s average net assets used to pay its annual administrative and advisory expenses. These expenses directly reduce returns to investors.


Foreign Holdings. The percentage of a fund’s equity assets represented by stocks or depositary receipts of companies based outside the United States.


Median Market Cap. An indicator of the size of companies in which a fund invests; the midpoint of market capitalization (market price x shares outstanding) of a fund’s stocks, weighted by the proportion of the fund’s assets invested in each stock. Stocks representing half of the fund’s assets have market capitalizations above the median, and the rest are below it.


Price/Book Ratio. The share price of a stock divided by its net worth, or book value, per share. For a fund, the weighted average price/book ratio of the stocks it holds.


Price/Earnings Ratio. The ratio of a stock’s current price to its per-share earnings over the past year. For a fund, the weighted average P/E of the stocks it holds. P/E is an indicator of market expectations about corporate prospects; the higher the P/E, the greater the expectations for a company’s future growth.


R-Squared. A measure of how much of a fund’s past returns can be explained by the returns from the market in general, as measured by a given index. If a fund’s total returns were precisely synchronized with an index’s returns, its R-squared would be 1.00. If the fund’s returns bore no relationship to the index’s returns, its R-squared would be 0.


Return on Equity. The annual average rate of return generated by a company during the past five years for each dollar of shareholder’s equity (net income divided by shareholder’s equity). For a fund, the weighted average return on equity for the companies whose stocks it holds.


Short-Term Reserves. The percentage of a fund invested in highly liquid, short-term securities that can be readily converted to cash.


Turnover Rate. An indication of the fund’s trading activity. Funds with high turnover rates incur higher transaction costs and may be more likely to distribute capital gains (which may be taxable to investors).


Yield. A snapshot of a fund’s income from interest and dividends. The yield, expressed as a percentage of the fund’s net asset value, is based on income earned over the past 30 days and is annualized, or projected forward for the coming year. The index yield is based on the current annualized rate of income provided by securities in the index.




10



As of 4/30/2005

PERFORMANCE SUMMARY

All of the returns in this report represent past performance, which is not a guarantee of future results that may be achieved by the fund. (For performance data current to the most recent month-end, which may be higher or lower than that cited, visit our website at www.vanguard.com.) Note, too, that both investment returns and principal value can fluctuate widely, so an investor’s shares, when sold, could be worth more or less than their original cost. The returns shown do not reflect taxes that a shareholder would pay on fund distributions or on the sale of fund shares.

WINDSOR FUND


Fiscal-Year Total Returns (%) October 31, 1994–April 30, 2005

*Six months ended April 30, 2005.
Note: See Financial Highlights tables on pages 18 and 19 for dividend and capital gains information.





Average Annual Total Returns for periods ended March 31, 2005

This table presents average annual total returns through the latest calendar quarter—rather than through the end of the fiscal period. Securities and Exchange Commission rules require that we provide this information.

  Ten Years
 
 
Inception Date

One
Year

Five
Years

 
Capital

 
Income

 
Total

Windsor Fund            
  Investor Shares 10/23/1958 8.38% 7.80% 9.79% 1.88% 11.67%
  Admiral Shares 11/12/2001 8.49    7.74*

*Return since inception.



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As of 4/30/2005

FINANCIAL STATEMENTS (UNAUDITED)

STATEMENT OF NET ASSETS

This Statement provides a detailed list of the fund’s holdings, including each security’s market value on the last day of the reporting period. Securities are grouped and subtotaled by asset type (common stocks, bonds, etc.) and by industry sector. Other assets are added to, and liabilities are subtracted from, the value of Total Investments to calculate the fund’s Net Assets. Finally, Net Assets are divided by the outstanding shares of the fund to arrive at its share price, or Net Asset Value (NAV) Per Share.

At the end of the Statement of Net Assets, you will find a table displaying the composition of the fund’s net assets. Because all income and any realized gains must be distributed to shareholders each year, the bulk of net assets consists of Paid-in Capital (money invested by shareholders). The amounts shown for Undistributed Net Investment Income and Accumulated Net Realized Gains usually approximate the sums the fund had available to distribute to shareholders as income dividends or capital gains as of the statement date, but may differ because certain investments or transactions may be treated differently for financial statement and tax purposes. Any Accumulated Net Realized Losses, and any cumulative excess of distributions over net income or net realized gains, will appear as negative balances. Unrealized Appreciation (Depreciation) is the difference between the market value of the fund’s investments and their cost, and reflects the gains (losses) that would be realized if the fund were to sell all of its investments at their statement-date values.

The fund provides a complete list of its holdings four times in each fiscal year, at the quarter-ends. For the second and fourth fiscal quarters, the lists appear in the fund’s semiannual and annual reports to shareholders. For the first and third fiscal quarters, the fund files the lists with the Securities and Exchange Commission on Form N-Q. Shareholders can look up the fund’s Forms N-Q on the SEC’s website at www.sec.gov. Forms N-Q may also be reviewed and copied at the SEC’s Public Reference Room (see the back cover of this report for further information).




 
 
Windsor Fund
 
 
Shares
Market
Value^
(000)

COMMON STOCKS (97.7%)(1)    

Auto & Transportation (5.6%)
*Compagnie Generale des
 Etablissements Michelin
 Class B 6,550,773  $  398,602 
 Lear Corp. 2,976,000  100,857 
*Yellow Roadway Corp. 1,961,000  96,089 
 Burlington Northern
 Santa Fe Corp. 1,949,000  94,039 
 Norfolk Southern Corp. 2,727,650  85,648 
 Canadian National Railway Co. 1,370,000  78,378 
 CSX Corp. 1,619,900  65,007 
*(2) Continental Airlines, Inc.
 Class B 5,332,500  63,137 
*AMR Corp. 5,076,600  53,152 
 Magna International, Inc.
 Class A 738,700  45,157 
*Northwest Airlines Corp.
 Class A 4,248,058  22,005 
 BorgWarner, Inc. 468,800  21,434 

      1,123,505 

Consumer Discretionary (8.5%)
*Time Warner, Inc. 24,834,400  417,466 
 TJX Cos., Inc. 15,920,300  360,595 
(2)Ross Stores, Inc. 8,338,500  222,805 
 Gannett Co., Inc. 1,909,200  147,008 
 Republic Services, Inc. Class A 2,876,400  99,523 
*Office Depot, Inc. 3,305,000  64,712 
 McDonald's Corp. 2,195,000  64,335 
*Interpublic Group of Cos., Inc. 3,970,000  51,054 
 Target Corp. 1,085,000  50,355 
 Jones Apparel Group, Inc. 1,485,000  45,218 
 Federated Department
 Stores, Inc. 760,300  43,717 
 Whirlpool Corp. 650,000  40,339 
 VF Corp. 500,100  28,301 
 Kimberly-Clark Corp. 425,000  26,541 
 Staples, Inc. 1,287,150  24,546 
 Liz Claiborne, Inc. 677,000  23,986 

      1,710,501 




12





 
 
 
 
Shares
Market
Value^
(000)

Consumer Staples (2.3%)
 Altria Group, Inc. 2,099,800  $  136,466 
*Safeway, Inc. 2,891,600  61,562 
 PepsiCo, Inc. 1,090,000  60,648 
 Unilever NV ADR 905,000  58,309 
*The Kroger Co. 3,591,350  56,636 
 The Procter & Gamble Co. 994,000  53,825 
 SuperValu Inc. 942,100  29,733 

      457,179 

Financial Services (25.5%)
 Banks-New York City (0.6%)
 JPMorgan Chase & Co. 3,325,800  118,033 
 Banks-Outside New York City (6.4%)
 Bank of America Corp. 16,323,946  735,231 
 UnionBanCal Corp. 2,558,600  157,507 
 Wachovia Corp. 2,531,300  129,552 
 U.S. Bancorp 3,190,121  89,004 
 National City Corp. 2,185,700  74,226 
 SunTrust Banks, Inc. 980,000  71,373 
 Wells Fargo & Co. 510,000  30,569 
 Diversified Financial Services (7.6%)
 Citigroup, Inc. 22,590,246  1,060,838 
 CIT Group Inc. 5,017,000  202,085 
 Metropolitan Life Insurance Co. 1,773,100  68,974 
 Merrill Lynch & Co., Inc. 1,180,000  63,637 
 Marsh & McLennan Cos., Inc. 2,200,000  61,666 
 The Goldman Sachs Group, Inc. 565,000  60,336 
 Finance Companies (0.3%)
 Capital One Financial Corp. 712,500  50,509 
 Financial-Miscellaneous (2.5%)
 Fannie Mae 3,750,400  202,334 
 Freddie Mac 2,978,000  183,207 
 MBNA Corp. 5,730,600  113,179 
 Insurance-Multiline (2.9%)
 The Hartford Financial
 Services Group Inc. 5,476,800  396,356 
 St. Paul Travelers Cos., Inc. 1,836,917  65,762 
 Torchmark Corp. 1,182,800  63,197 
 Allstate Corp. 833,100  46,787 
 American International
 Group, Inc. 365,200  18,570 
 Insurance-Property-Casualty (3.9%)
 ACE Ltd. 4,794,700  205,980 
(2)RenaissanceRe Holdings Ltd. 4,167,300  186,570 
 PartnerRe Ltd. 1,897,900  110,610 
 IPC Holdings Ltd. 2,074,300  78,056 
 The Chubb Corp. 907,500  74,215 
 XL Capital Ltd. Class A 980,000  68,894 
 Everest Re Group, Ltd. 460,000  37,812 
 The PMI Group Inc. 460,600  16,195 
 Real Estate Investment Trusts (0.1%)
 Liberty Property Trust REIT 574,000  22,862 
 Savings & Loan (0.8%)
 Golden West Financial Corp. 2,608,400  162,582 
*Dime Bancorp Inc.-Litigation
 Tracking Warrants 7,457,300  1,044 
 Securities Brokers & Services (0.4%)
 Lehman Brothers Holdings, Inc. 912,900  83,731 

      5,111,483 

Health Care (13.0%)
 Wyeth 12,736,300  572,369 
 Sanofi-Synthelabo SA ADR 10,508,300  466,253 
 Pfizer Inc. 13,930,885  378,502 
 GlaxoSmithKline PLC ADR 5,717,900  289,040 
*(2) Health Net Inc. 6,359,560  216,416 
*WellPoint Inc. 1,614,800  206,291 
*Sanofi-Aventis 2,156,523  191,583 
 GlaxoSmithKline PLC 4,975,843  125,844 
*Medco Health Solutions, Inc. 1,790,000  91,236 
 HCA Inc. 1,317,100  73,547 

      2,611,081 

Integrated Oils (6.1%)
ExxonMobil Corp. 4,869,008  277,680 
Petrol Brasil ADR 4,643,000  194,681 
ConocoPhillips Co. 1,581,899  165,862 
Petro Canada 2,950,600  163,699 
ChevronTexaco Corp. 2,833,478  147,341 
Occidental Petroleum Corp. 1,588,200  109,586 
Petrol Brasil Series A ADR 2,579,500  94,797 
Royal Dutch Petroleum Co. ADR 761,900  44,381 
Total SA ADR 321,300  35,635 

     1,233,662 

Other Energy (1.1%)
GlobalSantaFe Corp. 3,424,900  115,077 
EnCana Corp. 1,547,719  98,837 

     213,914 

Materials & Processing (5.2%)
Alcoa Inc. 16,590,868  481,467 
(2)Engelhard Corp. 6,986,200  213,987 
 Smurfit-Stone Container Corp. 8,523,263  111,740 
*Akzo Nobel NV 1,430,424  58,840 
 MeadWestvaco Corp. 1,835,400  54,053 
 Martin Marietta Materials, Inc. 570,000  31,344 



13





 
 
Windsor Fund
 
 
Shares
Market
Value^
(000)

 Vulcan Materials Co. 550,000  $  29,172 
 International Paper Co. 680,000  23,317 
 Sappi Ltd. ADR 1,687,600  16,842 
 Praxair, Inc. 260,500  12,199 
 Aracruz Celulose SA ADR 51,000  1,566 

      1,034,527 

Producer Durables (5.4%)
*Applied Materials, Inc. 30,482,200  453,270 
 Goodrich Corp. 3,316,800  133,667 
*LAM Research Corp. 4,858,300  124,615 
 LM Ericsson Telephone Co.
 ADR Class B 3,820,800  112,522 
*Teradyne, Inc. 6,557,100  72,259 
 The Boeing Co. 1,145,000  68,150 
 Cooper Industries, Inc. Class A 936,000  59,586 
*Varian Semiconductor
 Equipment Associates, Inc. 585,400  21,830 
 Hubbell Inc. Class B 419,800  18,240 
*Axcelis Technologies, Inc. 1,726,000  10,718 

      1,074,857 

Technology (10.6%)
*Cisco Systems, Inc. 31,184,100  538,861 
 Microsoft Corp. 18,785,500  475,273 
*(2) Arrow Electronics, Inc. 10,542,000  256,592 
*(2) Freescale Semiconductor Inc.
 Class A 9,619,900  180,085 
 Hewlett-Packard Co. 5,661,300  115,887 
 International Business
 Machines Corp. 1,452,500  110,942 
*Flextronics International Ltd. 9,697,900  108,132 
*Avnet, Inc. 5,081,600  95,991 
*Ingram Micro, Inc. Class A 2,670,500  44,491 
*Vishay Intertechnology, Inc. 3,215,321  34,372 
*Solectron Corp. 10,387,300  34,278 
 Electronic Data Systems Corp. 1,700,000  32,895 
*Tellabs, Inc. 3,970,900  30,814 
*Sanmina-SCI Corp. 6,312,400  25,313 
*Nortel Networks Corp. 8,159,500  20,317 
*Unisys Corp. 2,398,200  15,564 
 Scientific-Atlanta, Inc. 478,600  14,636 

      2,134,443 

Utilities (8.6%)
*Comcast Corp. Special Class A 21,428,200  679,917 
*Nextel Communications, Inc. 12,712,600  355,826 
 Sprint Corp. 9,286,350  206,714 
 Constellation Energy Group, Inc. 1,506,425  79,178 
*Comcast Corp. Class A 2,415,683  77,568 
 Entergy Corp. 1,009,600  74,004 
 American Electric
 Power Co., Inc. 1,905,300  67,105 
 FirstEnergy Corp. 1,195,100  52,011 
 Verizon Communications Inc. 1,245,442  44,587 
 Sempra Energy 801,700  32,373 
 SBC Communications Inc. 1,146,900  27,296 
 Northeast Utilities 1,206,900  22,098 
*UnitedGlobalCom Inc. Class A 1,372,500  12,284 

      1,730,961 

Other (5.8%)
Tyco International Ltd. 19,073,300  597,185 
General Electric Co. 7,000,000  253,400 
Eaton Corp. 2,679,400  157,147 
Textron, Inc. 1,142,000  86,050 
Miscellaneous (0.3%)**    60,844 

     1,154,626 

TOTAL COMMON STOCKS
 (Cost $16,125,460)    19,590,739 

TEMPORARY INVESTMENTS (6.5%)(1)

Exchange-Traded Funds (0.8%)
 Vanguard Index Participation
 Equity Receipts
 Value 1,689,100  90,181 
 Total Stock Market 696,000  78,182 

      168,363 

Money Market Fund (4.0%)
 Vanguard Market
 Liquidity Fund, 2.829%† 216,635,350  216,635 
 Vanguard Market Liquidity
 Fund, 2.829%†-Note G 583,315,400  583,315 

      799,950 

   Face Amount    
   (000)   

Repurchase Agreement (1.6%)
Bank of America Securities
 2.970%, 5/2/2005 $325,200  325,200 
 (Dated 4/29/2005,
 Repurchase Value $325,280,000
 collateralized by Federal National
 Mortgage Assn
 6.000%, 4/1/2035)
U.S. Agency Obligation (0.1%)
Federal Home Loan Mortgage Corp.††
(3)3.002%, 7/19/2005 25,000  24,838 

TOTAL TEMPORARY INVESTMENTS
   (Cost $1,290,877)    1,318,351 

TOTAL INVESTMENTS (104.2%)
   (Cost $17,416,337)    20,909,090 




14





  Market 
  Value^ 
  (000)

OTHER ASSETS AND
LIABILITIES-NET (-4.2%) $(835,041)

NET ASSETS (100%) $20,074,049 

^See Note A in Notes to Financial Statements. *Non-income-producing security.
**Securities representing up to 5% of the market value of unaffiliated securities are permitted to be combined and reported as “miscellaneous securities” provided that they have been held for less than one year and not previously reported by name.
† Money market fund available only to Vanguard funds and certain trusts and accounts managed by Vanguard. Rate shown is the 7-day yield.
††The issuer operates under a congressional charter; its securities are neither issued nor guaranteed by the U.S. government. If needed, access to additional funding from the U.S. Treasury (beyond the issuer’s line of credit) would require congressional action.
(1)The fund invests a portion of its cash reserves in equity markets through the use of index futures contracts and exchange-traded funds. After giving effect to these investments, the fund’s effective common stock and temporary cash investment positions represent 99.6% and 4.6%, respectively, of net assets. See Note E in Notes to Financial Statements.
(2)Considered an affiliated company of the fund as the fund owns more than 5% of the outstanding voting securities of such company. See Note I in Notes to Financial Statements.
(3)Securities with a value of $24,838,000 have been segregated as initial margin for open futures contracts.
ADR—American Depositary Receipt.
REIT—Real Estate Investment Trust.



STATEMENT OF ASSETS AND LIABILITIES
Assets  
  Investment in Securities, at Value $20,909,090 
  Receivables for Investment Securities Sold 114,756 
  Receivables for Capital Shares Issued 12,674 
  Other Assets-Note C 33,536 

    Total Assets 21,070,056 

Liabilities
  Security Lending Collateral
    Payable to Brokers-Note G 583,315 
  Payables for Investment Securities Purchased 357,294 
  Other Liabilities 55,398 

    Total Liabilities 996,007 


  NET ASSETS (100%) $20,074,049 




 
 

Amount
(000)

AT APRIL 30, 2005, NET ASSETS CONSISTED OF:

Paid-in Capital $15,663,106 
Undistributed Net Investment Income 60,630 
Accumulated Net Realized Gains 868,215 
Unrealized Appreciation (Depreciation)
Investment Securities 3,492,753 
Futures Contracts (10,655)

NET ASSETS $20,074,049 

 
Investor Shares-Net Assets
Applicable to 895,871,541 outstanding $.001
par value shares of beneficial interest
(unlimited authorization) $15,544,945 

NET ASSET VALUE PER SHARE-
INVESTOR SHARES $17.35 

 
Admiral Shares-Net Assets
Applicable to 77,320,696 outstanding $.001
par value shares of beneficial interest
(unlimited authorization) $4,529,104 

NET ASSET VALUE PER SHARE-
ADMIRAL SHARES $58.58 

See Note E in Notes to Financial Statements for the tax-basis components of net assets.

15




STATEMENT OF OPERATIONS

This Statement shows the types of income earned by the fund during the reporting period, and details the operating expenses charged to each class of its shares. These expenses directly reduce the amount of investment income available to pay to shareholders as income dividends. This Statement also shows any Net Gain (Loss) realized on the sale of investments, and the increase or decrease in the Unrealized Appreciation (Depreciation) of investments during the period.




 
 
 

Windsor Fund
Six Months Ended April 30, 2005
(000)

INVESTMENT INCOME  
Income
Dividends* $190,296 
Interest 8,508 
Security Lending 725 

Total Income 199,529 

Expenses
Investment Advisory Fees-Note B
Basic Fee 12,779 
Performance Adjustment 2,731 
The Vanguard Group-Note C
Management and Administrative
Investor Shares 15,994 
Admiral Shares 2,092 
Marketing and Distribution
Investor Shares 866 
Admiral Shares 274 
Custodian Fees 123 
Shareholders' Reports
Investor Shares 135 
Admiral Shares
Trustees' Fees and Expenses 19 

Total Expenses 35,015 
Expenses Paid Indirectly-Note D (968)

Net Expenses 34,047 

NET INVESTMENT INCOME 165,482 

REALIZED NET GAIN (LOSS)
Investment Securities Sold* 850,215 
Futures Contracts 23,888 

REALIZED NET GAIN (LOSS) 874,103 

CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
Investment Securities (61,993)
Futures Contracts (15,018)

CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION) (77,011)

NET INCREASE (DECREASE) IN NET ASSETS RESULTING FROM OPERATIONS $962,574 

*Dividend income and realized net gain (loss) from affiliated companies of the fund were $5,853,000 and $39,088,000, respectively. See Note I in Notes to Financial Statements.


16


STATEMENT OF CHANGES IN NET ASSETS

This Statement shows how the fund’s total net assets changed during the two most recent reporting periods. The Operations section summarizes information detailed in the Statement of Operations. The amounts shown as Distributions to shareholders from the fund’s net income and capital gains may not match the amounts shown in the Operations section, because distributions are determined on a tax basis and may be made in a period different from the one in which the income was earned or the gains were realized on the financial statements. The Capital Share Transactions section shows the net amount shareholders invested in or redeemed from the fund. Distributions and Capital Share Transactions are shown separately for each class of shares.




  Windsor Fund
 
 
 
 

Six Months
Ended
April 30, 2005
(000)

Year
Ended
Oct. 31, 2004
(000)

INCREASE (DECREASE) IN NET ASSETS    
Operations
Net Investment Income $  165,482  $  251,401 
Realized Net Gain (Loss) 874,103  1,223,100 
Change in Unrealized Appreciation (Depreciation) (77,011) 475,801 

Net Increase (Decrease) in Net Assets Resulting from Operations 962,574  1,950,302 

Distributions
Net Investment Income
Investor Shares (134,519) (175,846)
Admiral Shares (40,103) (51,410)
Realized Capital Gain
Investor Shares (78,917) — 
Admiral Shares (22,180) — 

Total Distributions (275,719) (227,256)

Capital Share Transactions-Note H
Investor Shares (125,516) 24,026 
Admiral Shares 188,107  523,427 

Net Increase (Decrease) from Capital Share Transactions 62,591  547,453 

Total Increase (Decrease) 749,446  2,270,499 

Net Assets
Beginning of Period 19,324,603  17,054,104 

End of Period $20,074,049  $19,324,603 



17




FINANCIAL HIGHLIGHTS

This table summarizes the fund’s investment results and distributions to shareholders on a per-share basis for each class of shares. It also presents the Total Return and shows net investment income and expenses as percentages of average net assets. These data will help you assess: the variability of the fund’s net income and total returns from year to year; the relative contributions of net income and capital gains to the fund’s total return; how much it costs to operate the fund; and the extent to which the fund tends to distribute capital gains. The table also shows the Portfolio Turnover Rate, a measure of trading activity. A turnover rate of 100% means that the average security is held in the fund for one year.



 
Windsor Fund Investor Shares

  Year Ended October 31,
 
 
For a Share Outstanding Throughout Each Period

Six Months
Ended
April 30, 2005

 
 
2004

 
 
2003

 
 
2002

 
 
2001

 
 
2000

Net Asset Value, Beginning of Period
$16.75
$15.23
$11.81
$14.27
$16.44
$16.91
Investment Operations            
Net Investment Income .142* .214  .17  .164  .22  .28 
Net Realized and Unrealized Gain (Loss) on Investments .696  1.501  3.42  (2.143) (.29) 1.44 

Total from Investment Operations .838  1.715  3.59  (1.979) (.07) 1.72 

Distributions
Dividends from Net Investment Income (.150) (.195) (.17) (.169) (.25) (.29)
Distributions from Realized Capital Gains (.088) —  —  (.312) (1.85) (1.90)

Total Distributions (.238) (.195) (.17) (.481) (2.10) (2.19)

Net Asset Value, End of Period $17.35  $16.75  $15.23  $11.81  $14.27  $16.44 

 
Total Return 4.98% 11.30% 30.66% -14.55%  -0.37%  11.60%

Ratios/Supplemental Data
Net Assets, End of Period (Millions) $15,545  $15,130  $13,733  $11,012  $15,761  $15,935 
Ratio of Total Expenses to
Average Net Assets** 0.37%† 0.39% 0.48% 0.45% 0.41% 0.31%
Ratio of Net Investment Income to
Average Net Assets 1.42%*† 1.32% 1.27% 1.16% 1.37% 1.75%
Portfolio Turnover Rate 36%† 28% 23% 30% 33% 41%

*Net investment income per share and the ratio of net investment income to average net assets include $0.03 and 0.18%, respectively, resulting from a special dividend from Microsoft Corp. in November 2004.
**Includes performance-based investment advisory fee increases (decreases) of 0.03%, 0.04%, 0.08%, 0.08%, 0.03%, and (0.08%).
† Annualized.


18





Windsor Fund Admiral Shares
  Six Months
Ended
Year Ended
October 31,

Nov.12,
2001* to
Oct. 31,
For a Share Outstanding Throughout Each Period April 30,2005 2004 2003 2002

Net Asset Value, Beginning of Period $56.56  $51.41  $39.88  $50.00 

Investment Operations
Net Investment Income .511** .787  .605  .556 
Net Realized and Unrealized Gain (Loss) on Investments 2.343  5.082  11.537  (9.030)

Total from Investment Operations 2.854  5.869  12.142  (8.474)

Distributions
Dividends from Net Investment Income (.537) (.719) (.612) (.592)
Distributions from Realized Capital Gains (.297) —  —  (1.054)

Total Distributions (.834) (.719) (.612) (1.646)

Net Asset Value, End of Period $58.58  $56.56  $51.41  $39.88 

 
Total Return 5.02% 11.46% 30.72% -17.61% 

Ratios/Supplemental Data
Net Assets, End of Period (Millions) $4,529  $4,195  $3,321  $2,214 
Ratio of Total Expenses to Average Net Assets† 0.26%†† 0.28% 0.37% 0.40%†
Ratio of Net Investment Income to Average Net Assets 1.52**†† 1.43% 1.36% 1.22%†
Portfolio Turnover Rate 36%†† 28% 23% 30%

  *Inception
**Net investment income per share and the ratio of net investment income to average net assets include $0.11 and 0.18%, respectively, resulting from a special dividend from Microsoft Corp. in November 2004.
  † Includes performance-based investment advisory fee increases (decreases) of 0.03%, 0.04%, 0.08%, and 0.08%.
††Annualized.



SEE ACCOMPANYING NOTES, WHICH ARE AN INTEGRAL PART OF THE FINANCIAL STATEMENTS.




19




NOTES TO FINANCIAL STATEMENTS

Vanguard Windsor Fund is registered under the Investment Company Act of 1940 as an open-end investment company, or mutual fund. The fund offers two classes of shares, Investor Shares and Admiral Shares. Investor Shares are available to any investor who meets the fund’s minimum purchase requirements. Admiral Shares are designed for investors who meet certain administrative, servicing, tenure, and account-size criteria.

A.   The following significant accounting policies conform to generally accepted accounting principles for U.S. mutual funds. The fund consistently follows such policies in preparing its financial statements.

1.Security Valuation: Securities are valued as of the close of trading on the New York Stock Exchange (generally 4:00 p.m. Eastern time) on the valuation date. Equity securities are valued at the latest quoted sales prices or official closing prices taken from the primary market in which each security trades; such securities not traded on the valuation date are valued at the mean of the latest quoted bid and asked prices. Securities for which market quotations are not readily available, or whose values have been materially affected by events occurring before the fund’s pricing time but after the close of the securities’ primary markets, are valued by methods deemed by the board of trustees to represent fair value. Investments in Vanguard Market Liquidity Fund are valued at that fund’s net asset value. Temporary cash investments acquired over 60 days to maturity are valued using the latest bid prices or using valuations based on a matrix system (which considers such factors as security prices, yields, maturities, and ratings), both as furnished by independent pricing services. Other temporary cash investments are valued at amortized cost, which approximates market value.

2.Futures Contracts: The fund uses S&P 500 Index and S&P MidCap 400 Index futures contracts to a limited extent, with the objective of maintaining full exposure to the stock market while maintaining liquidity. The fund may purchase or sell futures contracts to achieve a desired level of investment, whether to accommodate portfolio turnover or cash flows from capital share transactions. The primary risks associated with the use of futures contracts are imperfect correlation between changes in market values of stocks held by the fund and the prices of futures contracts, and the possibility of an illiquid market.

Futures contracts are valued at their quoted daily settlement prices. The aggregate principal amounts of the contracts are not recorded in the financial statements. Fluctuations in the value of the contracts are recorded in the Statement of Net Assets as an asset (liability) and in the Statement of Operations as unrealized appreciation (depreciation) until the contracts are closed, when they are recorded as realized futures gains (losses).

3.Repurchase Agreements: The fund may invest in repurchase agreements. Securities pledged as collateral for repurchase agreements are held by a custodian bank until the agreements mature. Each agreement requires that the market value of the collateral be sufficient to cover payments of interest and principal; however, in the event of default or bankruptcy by the other party to the agreement, retention of the collateral may be subject to legal proceedings.

4.Federal Income Taxes: The fund intends to continue to qualify as a regulated investment company and distribute all of its taxable income. Accordingly, no provision for federal income taxes is required in the financial statements.

5.Distributions: Distributions to shareholders are recorded on the ex-dividend date.

6.Security Lending: The fund may lend its securities to qualified institutional borrowers, to earn additional income. Security loans are required to be secured at all times by collateral at least equal to the market value of securities loaned. The fund invests cash collateral received in Vanguard Market Liquidity Fund, and records a liability for the return of the collateral, during the period the securities are on loan. Security lending income represents the income earned on investing cash collateral, less expenses associated with the loan.

7.Other: Dividend income is recorded on the ex-dividend date. Interest income includes income distributions received from Vanguard Market Liquidity Fund and is accrued daily. Security transactions are accounted for on the date securities are bought or sold. Costs used to determine realized gains (losses) on the sale of investment securities are those of the specific securities sold.



20




Each class of shares has equal rights as to assets and earnings, except that each class separately bears certain class-specific expenses related to maintenance of shareholder accounts (included in Management and Administrative expenses) and shareholder reporting. Marketing and distribution expenses are allocated to each class of shares based on a method approved by the board of trustees. Income, other non-class-specific expenses, and gains and losses on investments are allocated to each class of shares based on its relative net assets.

B.   Wellington Management Company, LLP, and Sanford C. Bernstein & Co., LLC, each provide investment advisory services to a portion of the fund for a fee calculated at an annual percentage rate of average net assets managed by the advisor. The basic fees of each advisor are subject to quarterly adjustments based on performance for the preceding three years relative to a designated market index: for Wellington Management Company, LLP, the S&P 500 Index; and for Sanford C. Bernstein & Co., LLC, the Russell 1000 Value Index.

The Vanguard Group manages the cash reserves of the fund on an at-cost basis.

For the six months ended April 30, 2005, the aggregate investment advisory fee represented an effective annual basic rate of 0.13% of the fund’s average net assets before an increase of $2,731,000 (0.03%) based on performance.

C.   The Vanguard Group furnishes at cost corporate management, administrative, marketing, and distribution services. The costs of such services are allocated to the fund under methods approved by the board of trustees. The fund has committed to provide up to 0.40% of its net assets in capital contributions to Vanguard. At April 30, 2005, the fund had contributed capital of $2,653,000 to Vanguard (included in Other Assets), representing 0.01% of the fund’s net assets and 2.65% of Vanguard’s capitalization. The fund’s trustees and officers are also directors and officers of Vanguard.

D.   The fund has asked its investment advisors to direct certain security trades, subject to obtaining the best price and execution, to brokers who have agreed to rebate to the fund part of the commissions generated. Such rebates are used solely to reduce the fund’s management and administrative expenses. The fund’s custodian bank has also agreed to reduce its fees when the fund maintains cash on deposit in the non-interest-bearing custody account. For the six months ended April 30, 2005, these arrangements reduced the fund’s management and administrative expenses by $961,000 and custodian fees by $7,000. The total expense reduction represented an effective annual rate of 0.01% of the fund’s average net assets.

E.   Distributions are determined on a tax basis and may differ from net investment income and realized capital gains for financial reporting purposes. Differences may be permanent or temporary. Permanent differences are reclassified among capital accounts in the financial statements to reflect their tax character. Temporary differences arise when certain items of income, expense, gain, or loss are recognized in different periods for financial statement and tax purposes; these differences will reverse at some time in the future. Differences in classification may also result from the treatment of short-term gains as ordinary income for tax purposes. The fund’s tax-basis capital gains and losses are determined only at the end of each fiscal year.

At April 30, 2005, net unrealized appreciation of investment securities for tax purposes was $3,492,753,000, consisting of unrealized gains of $4,352,818,000 on securities that had risen in value since their purchase and $860,065,000 in unrealized losses on securities that had fallen in value since their purchase.

At April 30, 2005, the aggregate settlement value of open futures contracts expiring in June 2005 and the related unrealized appreciation (depreciation) were:




  (000)
 
 
Futures Contracts

 
Number of
Long Contracts

Aggregate
Settlement
Value

Unrealized
Appreciation
(Depreciation)

S&P 500 Index 593  $171,748  $(6,914)
S&P MidCap 400 Index 195  61,839  (3,761)
E-mini S&P 500 Index 35  2,027  20 



21




NOTES TO FINANCIAL STATEMENTS (CONTINUED)

Unrealized appreciation (depreciation) on open futures contracts is required to be treated as realized gain (loss) for tax purposes.

F.   During the six months ended April 30, 2005, the fund purchased $3,711,262,000 of investment securities and sold $3,500,376,000 of investment securities, other than temporary cash investments.

G.   The market value of securities on loan to broker/dealers at April 30, 2005, was $563,669,000, for which the fund held cash collateral of $583,315,000.

H.   Capital share transactions for each class of shares were:




 
 
Six Months Ended
April 30, 2005

Year Ended
October 31, 2004

 
 

Amount
(000)

Shares
(000)

Amount
(000)

Shares
(000)

Investor Shares        
Issued $714,603  40,401  $1,529,765  93,564 
Issued in Lieu of Cash Distributions 202,291  11,461  165,776  10,168 
Redeemed (1,042,410) (58,987) (1,671,515) (102,515)




Net Increase (Decrease)-Investor Shares (125,516) (7,125) 24,026  1,217 




Admiral Shares
Issued 343,193  5,751  883,845  16,096 
Issued in Lieu of Cash Distributions 57,700  969  47,570  864 
Redeemed (212,786) (3,572) (407,988) (7,399)




Net Increase (Decrease)-Admiral Shares 188,107  3,148  523,427  9,561 



I. Certain of the fund’s investments are in companies that are considered to be affiliated companies of the fund because the fund owns more than 5% of the outstanding voting securities of the company. Transactions during the period in securities of affiliated companies were as follows:




  (000)
  Current Period Transactions
 
 
 
 

Oct. 31, 2004
Market
Value

 
Purchases
at Cost

Proceeds from
Securities
Sold

 
Dividend
Income

Apr. 30, 2005
Market
Value

Arrow Electronics, Inc. $247,188  $5,628  $239  —  $256,592 
Continental Airlines, Inc. Class B 48,650  1,002  —  —  63,137 
Engelhard Corp. 252,589  —  56,274  $1,996  213,987 
Freescale Semiconductor Inc.
Class A 155,400  —  7,237  —  180,085 
Health Net Inc. 222,973  —  74,973  —  216,416 
IPC Holdings Ltd. 110,828  —  25,462  1,315  n/a* 
Northwest Airlines Corp. Class A 47,831  —  7,931  —  n/a* 
RenaissanceRe Holdings Ltd. 198,824  —  3,742  1,625  186,570 
Ross Stores, Inc. 286,784  —  74,809  917  222,805 



  $1,571,067     $5,853 $1,339,592




*At April 30, 2005, the security is still held but the issuer is no longer an affiliated company of the fund.


22




ABOUT YOUR FUND’S EXPENSES

As a shareholder of the fund, you incur ongoing costs, which include costs for portfolio management, administrative services, and shareholder reports (like this one), among others. Operating expenses, which are deducted from a fund’s gross income, directly reduce the investment return of the fund. A fund’s expenses are expressed as a percentage of its average net assets. This figure is known as the expense ratio. The following examples are intended to help you understand the ongoing costs (in dollars) of investing in your fund and to compare these costs with those of other mutual funds. The examples are based on an investment of $1,000 made at the beginning of the period shown and held for the entire period. The table below illustrates your fund’s costs in two ways:

Based on actual fund return. This section helps you to estimate the actual expenses that you paid over the period. The “Ending Account Value” shown is derived from the fund’s actual return, and the third column shows the dollar amount that would have been paid by an investor who started with $1,000 in the fund. You may use the information here, together with the amount you invested, to estimate the expenses that you paid over the period.

To do so, simply divide your account value by $1,000 (for example, an $8,600 account value divided by $1,000 = 8.6), then multiply the result by the number given for your fund under the heading “Expenses Paid During Period.”

Based on hypothetical 5% yearly return. This section is intended to help you compare your fund’s costs with those of other mutual funds. It assumes that the fund had a yearly return of 5% before expenses, but that the expense ratio is unchanged. In this case—because the return used is not the fund’s actual return—the results do not apply to your investment. The example is useful in making comparisons because the Securities and Exchange Commission requires all mutual funds to calculate expenses based on a 5% return. You can assess your fund’s costs by comparing this hypothetical example with the hypothetical examples that appear in shareholder reports of other funds.

Note that the expenses shown in the table are meant to highlight and help you compare ongoing costs only and do not reflect any transactional costs or account maintenance fees. They do not include your fund’s low-balance fee, which is described in the prospectus. If this fee were applied to your account, your costs would be higher. Your fund does not charge transaction fees, such as purchase or redemption fees, nor does it carry a “sales load.”




Six Months Ended April 30, 2005
 
 
Windsor Fund

Beginning
Account Value
10/31/2004

Ending
Account Value
4/30/2005

Expenses
Paid During
Period*

Based on Actual Fund Return      
Investor Shares $1,000.00  $1,049.79  $1.88 
Admiral Shares 1,000.00  1,050.22  1.32 

Based on Hypothetical 5% Yearly Return
Investor Shares $1,000.00  $1,022.96  $1.86 
Admiral Shares 1,000.00  1,023.51  1.30 

*The calculations are based on expenses incurred in the most recent six-month period. The fund’s annualized six-month expense ratios for that period are 0.37% for Investor Shares and 0.26% for Admiral Shares. The dollar amounts shown as “Expenses Paid” are equal to the annualized expense ratio multiplied by the average account value over the period, multiplied by the number of days in the most recent six-month period, then divided by the number of days in the most recent 12-month period.


The calculations assume no shares were bought or sold during the period. Your actual costs may have been higher or lower, depending on the amount of your investment and the timing of any purchases or redemptions. You can find more information about the fund’s expenses, including annual expense ratios, in the Financial Statements section of this report. For additional information on operating expenses and other shareholder costs, please refer to the appropriate fund prospectus.



23


INVESTING IS FAST, EASY, AND SECURE ON VANGUARD.COM

If you’re like many Vanguard investors, you believe in planning and taking control of your own investments. Vanguard.com was built for you—and it keeps getting better.

RESEARCH AND PLAN YOUR INVESTMENTS WITH CONFIDENCE

Use our Planning & Education and Research Funds & Stocks sections to:

• Determine what asset allocation might best suit your needs—by taking our Investor Questionnaire.

• Find out how much to save for retirement and your children’s college education—by using our planning tools.

• Learn how to achieve your goals—by reading our PlainTalk® investment guides.

• Find your next fund—by using the Compare Funds, Compare Fund Costs, and Narrow Your Fund Choices tools.

• Look up fund price, performance history, and distribution information—in a snap.


INVEST AND MANAGE ACCOUNTS WITH EASE

Log on to Vanguard.com to:

• See what you own (at Vanguard and elsewhere) and how your investments are doing.

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Find out what Vanguard.com can do for you. Log on today!



24


INVEST WITH VANGUARD FOR YOUR RE TIREMENT

Vanguard offers low-cost, high-quality solutions that combine a variety of investment choices to help you achieve your retirement goals.

A Vanguard traditional IRA enables you to make deductible or nondeductible contributions that can grow tax-deferred until you take distributions in retirement, while a Vanguard Roth IRA allows you to make nondeductible contributions with tax-free withdrawals when you take qualified distributions. With either type of Vanguard IRA®, your investment options include:

•Vanguard mutual funds
Select from our comprehensive lineup of more than 70 low-cost mutual funds suitable for retirement investing—all with no sales commissions—to help you reach your retirement goals. We offer a broad selection of stock, bond, balanced, and money market funds.

•Vanguard Target Retirement Funds
Choose a single, all-in-one portfolio that is professionally managed and well diversified. It automatically shifts from a more aggressive to a more conservative asset allocation as your target retirement date approaches, so you can leave the time-consuming details of portfolio management to Vanguard.

•Other investment options
Consolidate and build your portfolio in a single account that provides access to the universe of stocks, bonds, options, certificates of deposit (CDs), exchange-traded funds (ETFs), and non-Vanguard mutual funds through Vanguard Brokerage Services®.


ROLLOVER OPTIONS

When you change jobs or retire, you can take greater control of your investments by rolling over your assets in an employer-sponsored retirement plan to a Vanguard IRA. To initiate a rollover, visit Vanguard.com, where you can complete our easy online application. You can also print out the application and mail it to us—or call a Vanguard retirement specialist at 800-205-6189.









For more information, visit www.vanguard.com, or call 800-662-7447 for Vanguard funds and 800-992-8327 for non-Vanguard funds offered through Vanguard Brokerage Services, to obtain a prospectus. Investment objectives, risks, charges, expenses, and other important information are contained in the prospectus; read and consider it carefully before investing.





MAXIMIZE YOUR RETIREMENT INVESTMENTS

Are you taking full advantage of your IRA? You should be. With increased contribution limits, these tax-advantaged accounts are powerful options for retirement savers. To take full advantage of your retirement account, consider these simple, but important, steps:

•Contribute the maximum amount each year.
If you invest as much in your IRA as the law allows—$4,000 for 2005 if you are under the age of 50, and $4,500 if you are aged 50 or older—you will increase your chances of meeting your retirement goals. Provided you meet the eligibility requirements, max out your contribution every year you can.

•Make automatic contributions.
You can make regular contributions to your IRA by taking advantage of Vanguard’s Automatic Investment Plan, which deducts your contributions from your bank account on a schedule you select—making retirement investing a healthy habit.

•Keep your savings on course.
Unless you’ve invested in a Vanguard Target Retirement Fund, you should rebalance your account periodically to ensure that your target asset allocations are aligned to meet your retirement objectives.

•Protect those you care about.
You determine who will receive your retirement assets after your death, so it’s important to keep your beneficiary designations up to date. They will generally override any other instructions—even those in your will.

•Adopt a long-term approach.
A successful investment strategy requires a long-term perspective and staying on course—even when the financial markets are declining. Market-timing and performance-chasing are losing strategies that can cause you to stray from the path to your retirement goals.


If you have any questions about IRAs or would like to talk to a Vanguard retirement specialist, call 800-205-6189.
































THIS PAGE INTENTIONALLY LEFT BLANK.


THE PEOPLE WHO GOVERN YOUR FUND


The trustees of your mutual fund are there to see that the fund is operated and managed in your best interests since, as a shareholder, you are a part owner of the fund. Your fund trustees also serve on the board of directors of The Vanguard Group, Inc., which is owned by the Vanguard funds and provides services to them on an at-cost basis.

A majority of Vanguard's board members are independent, meaning that they have no affiliation with Vanguard or the funds they oversee, apart from the sizable personal investments they have made as private individuals.
 
Our independent board members bring distinguished backgrounds in business, academia, and public service to their task of working with Vanguard officers to establish the policies and oversee the activities of the funds. Among board members’ responsibilities are



Name
(Year of Birth)
Trustee/Officer
Since

Position(s) Held with
Fund (Number of
Vanguard Funds
Overseen by
Trustee/Officer)

Principal Occupation(s) During the Past Five Years
John J. Brennan*
(1954)
May 1987

Chairman of the
Board, Chief
Executive Officer,
and Trustee
(132)
Chairman of the Board,Chief Executive Officer, and Director/Trustee of The Vanguard Group, Inc., and of each of the investment companies served by The Vanguard Group.

INDEPENDENT TRUSTEES
Charles D. Ellis
(1937)
January 2001
Trustee
(132)
The Partners of `63 (pro bono ventures in education); Senior Advisor to Greenwich Associates (international business strategy consulting); Successor Trustee of Yale University; Overseer of the Stern School of Business at New York University; Trustee of the Whitehead Institute for Biomedical Research.

Rajiv L. Gupta
(1945)
December 2001**
Trustee
(132)
Chairman and Chief Executive Officer of Rohm and Haas Co. (chemicals); Board Member of the American Chemistry Council; Director of Tyco International, Ltd. (diversified manufacturing and services) (since 2005);Trustee of Drexel University and of the Chemical Heritage Foundation.

JoAnn Heffernan
Heisen

(1950)
July 1998
Trustee
(132)
Vice President, Chief Information Officer, and Member of the Executive Committee of Johnson & Johnson (pharmaceuticals/consumer products); Director of the University Medical Center at Princeton and Women's Research and Education Institute.

Burton G. Malkiel
(1932)
May 1977
Trustee
(129)
Chemical Bank Chairman's Professor of Economics, Princeton University; Director of Vanguard Investment Series plc (Irish investment fund) (since November 2001), Vanguard Group (Ireland) Limited (investment management) (since November 2001), BKF Capital (investment management), The Jeffrey Co. (holding company), and CareGain, Inc. (health care management).

André F. Perold
(1952)
December 2004
Trustee
(132)
George Gund Professor of Finance and Banking, Harvard Business School (since 2000); Senior Associate Dean, Director of Faculty Recruiting, and Chair of Finance Faculty, Harvard Business School; Director and Chairman of UNX, Inc. (equities trading firm) (since 2003); Director of registered investment companies advised by Merrill Lynch Investment Managers and affiliates (1985–2004), Genbel Securities Limited (South African financial services firm) (1999–2003), Gensec Bank (1999–2003), Sanlam Investment Management (1999–2001), Sanlam, Ltd. (South African insurance company) (2001–2003), Stockback, Inc. (credit card firm) (2000–2002), and Bulldogresearch.com (investment research) (1999–2001); and Trustee of Commonfund (investment management) (1989–2001).



selecting investment advisors for the funds; monitoring fund operations, performance, and costs; reviewing contracts; nominating and selecting new trustees/directors; and electing Vanguard officers.

Each trustee serves a fund until its termination; or until the trustee’s retirement, resignation, or death; or otherwise as specified in the fund’s organizational documents. Any trustee may be removed at a shareholders’ meeting by a vote representing two-thirds of the net asset value of all shares of the fund together with shares of other Vanguard funds organized within the same trust. The table on these two pages shows information for each trustee and executive officer of the fund. The mailing address of the trustees and officers is P.O. Box 876, Valley Forge, PA 19482.



Name
(Year of Birth)
Trustee/Officer
Since

Position(s) Held with
Fund (Number of
Vanguard Funds
Overseen by
Trustee/Officer)

Principal Occupation(s) During the Past Five Years
Alfred M. Rankin, Jr.
(1941)
January 1993
Trustee
(132)
Chairman, President, Chief Executive Officer, and Director of NACCO
Industries, Inc. (forklift trucks/housewares/lignite); Director of Goodrich Corporation (industrial products/aircraft systems and services); Director of Standard Products Company (supplier for the automotive industry) until 1998.

J. Lawrence Wilson
(1936)
April 1985
Trustee
(132)

Retired Chairman and Chief Executive Officer of Rohm and Haas Co. (chemicals); Director of Cummins Inc. (diesel engines), MeadWestvaco Corp. (packaging products), and AmerisourceBergen Corp. (pharmaceutical distribution); Trustee of Vanderbilt University and of Culver Educational Foundation.

EXECUTIVE OFFICERS*

R. Gregory Barton
(1951)
June 2001

Secretary
(132)

Managing Director and General Counsel of The Vanguard Group, Inc.; Secretary of The Vanguard Group, Inc. and of each of the investment
companies served by The Vanguard Group since June 2001.

Thomas J. Higgins
(1957)
July 1998
Treasurer
(132)
Principal of The Vanguard Group, Inc.; Treasurer of each of the investment companies served by The Vanguard Group.

* Officers of the funds are “interested persons” as defined in the Investment Company Act of 1940.
** December 2002 for Vanguard Equity Income Fund, Vanguard Growth Equity Fund, the Vanguard Municipal Bond Funds, and the Vanguard State Tax-Exempt Funds.

More information about the trustees is in the Statement of Additional Information, available from The Vanguard Group.




VANGUARD SENIOR MANAGEMENT TEAM

Mortimer J. Buckley, Information Technology.
James H. Gately, Investment Programs and Services.
Kathleen C. Gubanich, Human Resources.
F. William McNabb, III, Client Relationship Group.
Michael S. Miller, Planning and Development.
Ralph K. Packard, Finance.
George U. Sauter, Chief Investment Officer.



John C. Bogle, Founder; Chairman and Chief Executive Officer, 1974-1996.








Post Office Box 2600
Valley Forge, PA 19482-2600





Vanguard, The Vanguard Group, Vanguard Brokerage Services, Vanguard.com, Vanguard IRA, Admiral, PlainTalk, Windsor, and the ship logo are trademarks of The Vanguard Group, Inc.

All other marks are the exclusive property of their respective owners.

All comparative mutual fund data are from Lipper Inc. or Morningstar, Inc., unless otherwise noted.

For More Information
This report is intended for the fund’s shareholders. It may not be distributed to prospective investors unless it is preceded or accompanied by the current fund prospectus. To receive a free copy of the prospectus or the Statement of Additional Information, or to request additional information about the fund or other Vanguard funds, please contact us at one of the adjacent telephone numbers or by e-mail through Vanguard.com. Prospectuses may also be viewed online.

You can obtain a free copy of Vanguard’s proxy voting guidelines by visiting our website, www.vanguard.com, and searching for “proxy voting guidelines,” or by calling Vanguard at 800- 662-2739. They are also available from the SEC’s website, www.sec.gov. In addition, you may obtain a free report on how your fund voted the proxies for securities it owned during the 12 months ended June 30. To get the report, visit either www.vanguard.com or www.sec.gov.

You can review and copy information about your fund at the SEC’s Public Reference Room in Washington, D.C. To find out more about this public service, call the SEC at 202-942- 8090. Information about your fund is also available on the SEC’s website, and you can receive copies of this information, for a fee, by sending a request in either of two ways: via e-mail addressed to publicinfo@sec.gov or via regular mail addressed to the Public Reference Section, Securities and Exchange Commission, Washington, DC 20549–0102.

World Wide Web
www.vanguard.com

Fund Information
800-662-7447

Direct Investor
Account Services

800-662-2739

Institutional Investor
Services

800-523-1036

Text Telephone
800-952-3335

© 2005 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation, Distributor.
Q222 062005






  Vanguard® Windsor™ II Fund
 
April 30, 2005
Semi Annual


Your Fund Report
CONTENTS
CHAIRMAN'S LETTER
ADVISOR'S REPORT
FUND PROFILE
GLOSSARY OF INVESTMENT TERMS
PERFORMANCE SUMMARY
10  FINANCIAL STATEMENTS
24  ABOUT YOUR FUND'S EXPENSES
25  ADVISORY AGREEMENT
27  ADVANTAGES OF VANGUARD.COM

SUMMARY
During the six months ended April 30, 2005, Vanguard Windsor II Fund returned 8.3%.
The fund’s return outpaced the returns of the average competing fund, the fund’s benchmark index, and the broad U.S. stock market.
The advisors’ stock selections in three sectors—consumer staples, health care, and integrated oils—contributed the most to the fund’s return.



VANGUARD’S PLEDGE TO CLIENTS

We recognize that your relationship with Vanguard rests on the twin pillars of trust and excellence, each of which is built upon the character of our people. Our Pledge to Clients reflects our ongoing efforts to deserve your trust and to continually improve so that we can offer you excellence in all that we do.

We will:
Put your interests first at all times.
Continually seek to earn your trust by adhering to the highest standards of ethical behavior and fiduciary responsibility.
Strive to be the highest-value provider of investment services, which means outstanding investment performance and service, both at the lowest possible cost.
Communicate candidly not only about the rewards of investing but also about the risks and costs.
Maintain highly effective controls to safeguard your assets and protect your confidential information.
Invest a majority of our personal assets alongside yours.


Please note: The opinions expressed in this report are just that—informed opinions. They should not be considered promises or advice. Also, please keep in mind that the information and opinions cover the period through the date on the cover of this report. Of course, the risks of investing in your fund are spelled out in the prospectus.

Want less clutter in your mailbox? Just register with
Vanguard.com® and opt to get fund reports online.



       CHAIRMAN’S LETTER


Picture of John J. Brennan

Dear Shareholder,

Both the Investor Shares and the Admiral Shares of Vanguard Windsor II Fund returned 8.3% during the six months ended April 30, 2005. This performance exceeded the average return of the fund’s peer group and also topped the gains of the Russell 1000 Value Index and the Dow Jones Wilshire 5000 Composite Index, a measure of the overall U.S. equity market.

Windsor II’s strong showing during the period reflected the advisors’ emphasis on some of the market’s best-performing sectors and on some of the best-performing stocks within those sectors.



Total Returns Six Months Ended
April 30, 2005

Vanguard Windsor II Fund    
  Investor Shares  8.3 %
  Admiral Shares  8.3  
Russell 1000 Value Index  6.7  
Average Large-Cap Value Fund*  4.6  
Dow Jones Wilshire 5000 Index  3.5  

*Derived from data provided by Lipper Inc. 

The adjacent table shows the total returns—capital change plus reinvested dividends—for Windsor II’s Investor and Admiral Shares and the fund’s comparative measures. Information about the fund’s change in share prices during the period and per-share distributions appears in the table on page 4.

STOCKS STALLED AMID UNCERTAINTY

U.S. stocks rallied in the final months of 2004, then drifted lower as the New Year began. Although the economy registered respectable growth during the fiscal half-year, concern about the strength and durability of the expansion seemed to dictate the market’s direction. Segments of corporate America generated unexpectedly robust profits, for example, but every instance of good news seemed to be overshadowed by a high-profile disappointment. Persistently high oil prices and other specters of inflation also cast a pall on the market’s mood.

1




Admiral™ Shares
A lower-cost class of shares available to many longtime shareholders and to those with significant investments in the fund.


The Dow Jones Wilshire 5000 Index returned 3.5% for the six months. As has been the case for much of the past five years, value-oriented stocks outpaced their growth-oriented counterparts. In a reversal of recent trends, large-capitalization stocks bested the market’s smaller companies. On balance, international stocks generated higher returns than the U.S. market.

THE FED STEPPED TO THE FORE

In the bond market, the Federal Reserve Board commanded the spotlight, signaling that its near-term objective was to short-circuit any surge in inflation. The Fed raised its target for the federal funds rate to 2.75% during the half-year, a full percentage point higher than its level at the start of the period. (In early May, the Fed raised its target to 3.00%.) The steady increase in the yield of the 3-month U.S. Treasury bill paralleled the Fed’s actions, closing the period at 2.89%.

The impact on longer-term securities was less pronounced. The yield of the benchmark 10-year Treasury note rose 18 basis points to 4.20%, while the yields of the longest-term securities declined modestly.


Market Barometer Total Returns
Periods Ended April 30, 2005

Six
Months
One
Year
Five
Years*

Stocks        
Russell 1000 Index(Large-caps)  4.0 % 7.2 % -2.7 %
Russell 2000 Index(Small-caps)  -0.1   4.7   4.1  
Dow Jones Wilshire 5000 Index  3.5   7.0   -2.0  
  (Entire market)  
MSCI All Country World Index  
  ex USA (International)  9.1   16.9   0.6  




Bonds        
Lehman Aggregate Bond Index  1.0 % 5.3 % 7.5 %
  (Broad taxable market)  
Lehman Municipal Bond Index  1.9   6.8   7.0  
Citigroup 3-Month Treasury Bill Index  1.1   1.7   2.6  




CPI
Consumer Price Index   1.9 % 3.5 % 2.6 %

*Annualized

YOUR FUND’S ADVISORS MADE THE MOST OF A GOOD SITUATION

With its six-month return of 8.3%, the Windsor II Fund added to the impressive gains it achieved during the 2004 fiscal year. The success was partly a reflection of the advisors’ disciplined execution of the fund’s mandate to invest in stocks with modest valuations and relatively high dividend yields, since value stocks outpaced growth-oriented sectors such as technology during the half-year.

2


The result was also a credit to the advisors’ abilities to make the best of a good situation. In the consumer staples sector, for example, the fund earned impressive returns from several tobacco companies and food and beverage makers, including Imperial Tobacco Group and Altria Group—stocks distinguished by their attractive dividend yields. This sector accounted for a bigger proportion of Windsor II than it did of the Russell 1000 Value Index, a factor that helped the fund to top the index during the period.



Annualized Expense Ratios:
Your fund compared with its peer group
Investor
Shares
Admiral
Shares
Average
Large-Cap
Value
Fund

Windsor II Fund 0.35% 0.24% 1.41%*

* Peer-group expense ratio is derived from data provided by Lipper Inc. and captures information through year-end 2004.

The fund also had relatively large weightings in the health care and integrated oils sectors, and these stocks likewise proved to be key performers. The largest contribution to Windsor II’s return came from holdings in the health care sector, with strong performances from companies such as WellPoint and Baxter International. Among energy-related stocks, the fund earned strong returns from integrated oils giants Occidental Petroleum and ConocoPhillips, two of the fund’s top ten holdings.



Fund Assets Managed April 30, 2005
$Million Percentage

Barrow, Hanley, Mewhinney    
  & Strauss, Inc. $21,429  58%
Equinox Capital Management, LLC 4,364  12 
Tukman Capital Management, Inc. 4,035  11 
Vanguard Quantitative Equity Group 3,572  10 
Hotchkis & Wiley
  Capital Management, LLC 1,928 
Cash Investments* 1,377 

Total $36,705  100%

* These short-term reserves are invested by The Vanguard Group in equity index products to simulate investment in stocks. Each advisor may also maintain a modest cash position.

For more information about some of the fund’s individual holdings, see the Advisor’s Report, which begins on page 5.

Your fund is managed by five investment advisory firms. This combination of managers provides diversification in terms of the fund’s overall security selection, at a very modest cost.

The table at left shows the portion of fund assets that each of the five advisors managed at the end of the half-year. In June, Barrow, Hanley, Mewhinney & Strauss will mark its 20th year as the lead advisor to

3


the fund. Since the fund’s inception in 1985, your fund has benefited from this advisor’s discipline and skill in stock selection. We’re grateful for all that Jim Barrow and his team have done for the fund.

A TIME-TESTED STRATEGY

Since inception, the Windsor II Fund has followed essentially the same set of investment principles, seeking strong performance from the market’s less celebrated—and more reasonably valued—stocks. The strategy is not glitzy, and when growth stocks outperform, the fund’s approach can look out of step with the market’s beat. However, the fund’s strategy is disciplined and consistent, and over time it has been very successful.

This kind of discipline and consistency can be applied to your own investments. By sticking with a portfolio balanced among a mix of low-cost stock, bond, and money market mutual funds that fits your goals and tolerance for risk, investors enhance their ability to meet their long-term goals. If you continue to adhere to these essentials in your investment strategy, you’ll be positioned to benefit no matter what might occur in the financial markets.

Thank you for entrusting your assets to Vanguard.

Sincerely,

John J. Brennan

John J. Brennan

CHAIRMAN AND CHIEF EXECUTIVE OFFICER

MAY 12, 2005



Your Fund's Performance at a Glance October 31, 2004-April 30, 2005

Distributions Per Share

Starting
Share Price
Ending
Share Price
Income
Dividends
Capital
Gains

Windsor II Fund        
  Investor Shares $28.49  $30.54  $0.310  $0.000 
  Admiral Shares 50.59  54.22  0.577  0.000 

4



       ADVISOR’S REPORT


Vanguard Windsor II Fund returned 8.3% for the six months ended April 30, 2005, compared with 3.5% for the Standard & Poor’s 500/Barra Value Index and 6.7% for the Russell 1000 Value Index. The following comments concern the 58% of fund assets that Barrow, Hanley, Mewhinney & Strauss managed as of April 30; four additional advisors oversee the remaining assets.

THE INVESTMENT ENVIRONMENT

For the fiscal year to date, our portfolio has done well versus most benchmarks. You could say this is very much a market of individual stocks, rather than a stock market. The post-election rally has ended, and the underlying trend has gotten nasty. Disappointments, no matter how small, are treated severely by investors. The economy’s growth is slowing, but this is natural as the economic cycle matures and we approach normal capacity utilization. With high oil prices acting like a tax on stretched consumer budgets, organic growth is hard to find. Price increases in industrial commodities are difficult for companies to pass on to consumers, and the weak dollar doesn’t help anybody. Monthly increases in interest rates are also dampening economic activity. The long-term purge of excessive business practices continues. “Managed earnings” are no longer admired, and many of those who were best at it are taking early retirement. Dividends are growing faster than earnings and will likely continue to do so. This trend helps our portfolio because it has a bent towards earnings stability and dividend income.

Investment Philosophy
The fund reflects a belief that superior long-term investment results can be achieved by holding a diversified portfolio of out-of-favor stocks with below-average price/earnings ratios, above-average dividend yields, and the prospect of above-average total returns.

OUR SUCCESSES

Our successes include Occidental Petroleum, ConocoPhillips, WellPoint, and ITT, all of which have enjoyed strong earnings progress. We also benefited from our minimal exposure to Nasdaq and technology issues.

5


OUR SHORTFALLS

Our shortfalls included MBNA, which sold off after the company reported a greater-than-expected shrinkage of its loan portfolio and subsequent profit-margin compression. Verizon, Hewlett-Packard, Compaq (which merged with Hewlett-Packard), and International Paper all had earnings shortfalls.

OUR PORTFOLIO POSITIONING

Our portfolio positioning includes significant energy holdings, a large overweighting in electric utilities, and a growing list of investments in health care issues. From these concentrations we expect to enjoy a defensive stream of earnings. While we are exposed to higher interest rates through our financial stocks, we are significantly less concentrated there than are the benchmark indexes.

James P. Barrow, PORTFOLIO MANAGER

BARROW, HANLEY, MEWHINNEY & STRAUSS, INC.

MAY 12, 2005






6


As of 4/30/2005
FUND PROFILE
This Profile provides a snapshot of the fund's characteristics, compared where indicated with both an appropriate market index and a broad market index. Key terms are defined on page 8.


WINDSOR II FUND
Portfolio Characteristics Fund
Comparative
Index*
Broad
Index**

Number of Stocks 285  695  4,949 
Median Market Cap $37.6B  $32.7B  $26.4B 
Price/Earnings Ratio 15.6x  15.8x  21.2x 
Price/Book Ratio 2.4x  2.2x  2.6x 
Yield    2.5% 1.7%
  Investor Shares 2.1%      
  Admiral Shares 2.2%      
Return on Equity 20.8% 17.3% 15.0%
Earnings Growth Rate 8.9% 9.3% 9.0%
Foreign Holdings 7.8% 0.0% 1.0%
Turnover Rate 30%† —  — 
Expense Ratio    —  — 
  Investor Shares 0.35%†      
  Admiral Shares 0.24%†      
Short-Term Reserves 3% —  — 


Volatility Measures
Fund Comparative
Index*
Fund Broad
Index**

R-Squared 0.95  1.00  0.90  1.00 
Beta 0.94  1.00  0.94  1.00 



Sector Diversification (% of portfolio)
Fund Comparative
Index*
Broad
Index**

Auto & Transportation 1% 2% 2%
Consumer Discretionary 10    9    16   
Consumer Staples 10    6    7   
Financial Services 25    32    23   
Health Care 12    4    13   
Integrated Oils 10    10    4   
Other Energy 1    3    3   
Materials & Processing 3    5    4   
Producer Durables 6    4    5   
Technology 5    5    12   
Utilities 10    13    7   
Other 4    7    4   




Short-Term Reserves 3% —    —   



Ten Largest Holdings (% of total net assets)

Occidental Petroleum Corp.
3.0%
  (oil)
Wells Fargo & Co. 2.9   
  (banking)
ConocoPhillips Co. 2.8   
  (oil)
Pfizer Inc. 2.5   
  (pharmaceuticals)
Altria Group, Inc. 2.5   
  (tobacco)
Citigroup, Inc. 2.5   
  (banking)
Bank of America Corp. 2.3   
  (banking)
Washington Mutual, Inc. 2.2   
  (banking)
Cendant Corp. 2.0   
  (commercial services)
Imperial Tobacco Group ADR 2.0   
  (tobacco)

Top Ten 24.7%

“Ten Largest Holdings” excludes any temporary cash investments and equity index products.



Investment Focus

Investment Focus
* Russell 1000 Value Index.
** Dow Jones Wilshire 5000 Index. Visit our website at Vanguard.com
Annualized. for regularly updated fund information.

7



      GLOSSARY OF INVESTMENT TERMS


Beta. A measure of the magnitude of a fund’s past share-price fluctuations in relation to the ups and downs of a given market index. The index is assigned a beta of 1.00. Compared with a given index, a fund with a beta of 1.20 typically would have seen its share price rise or fall by 12% when the index rose or fell by 10%. A fund’s beta should be reviewed in conjunction with its R-squared (see definition below). The lower the R-squared, the less correlation there is between the fund and the index, and the less reliable beta is as an indicator of volatility.


Earnings Growth Rate. The average annual rate of growth in earnings over the past five years for the stocks now in a fund.


Expense Ratio. The percentage of a fund’s average net assets used to pay its annual administrative and advisory expenses. These expenses directly reduce returns to investors.


Foreign Holdings. The percentage of a fund’s equity assets represented by stocks or depositary receipts of companies based outside the United States.


Median Market Cap. An indicator of the size of companies in which a fund invests; the midpoint of market capitalization (market price x shares outstanding) of a fund’s stocks, weighted by the proportion of the fund’s assets invested in each stock. Stocks representing half of the fund’s assets have market capitalizations above the median, and the rest are below it.


Price/Book Ratio. The share price of a stock divided by its net worth, or book value, per share. For a fund, the weighted average price/book ratio of the stocks it holds.


Price/Earnings Ratio. The ratio of a stock’s current price to its per-share earnings over the past year. For a fund, the weighted average P/E of the stocks it holds. P/E is an indicator of market expectations about corporate prospects; the higher the P/E, the greater the expectations for a company’s future growth.


R-Squared. A measure of how much of a fund’s past returns can be explained by the returns from the market in general, as measured by a given index. If a fund’s total returns were precisely synchronized with an index’s returns, its R-squared would be 1.00. If the fund’s returns bore no relationship to the index’s returns, its R-squared would be 0.


Return on Equity. The annual average rate of return generated by a company during the past five years for each dollar of shareholder’s equity (net income divided by shareholder’s equity). For a fund, the weighted average return on equity for the companies whose stocks it holds.


Short-Term Reserves. The percentage of a fund invested in highly liquid, short-term securities that can be readily converted to cash.


Turnover Rate. An indication of the fund’s trading activity. Funds with high turnover rates incur higher transaction costs and may be more likely to distribute capital gains (which may be taxable to investors).


Yield. A snapshot of a fund’s income from interest and dividends. The yield, expressed as a percentage of the fund’s net asset value, is based on income earned over the past 30 days and is annualized, or projected forward for the coming year. The index yield is based on the current annualized rate of income provided by securities in the index.



8


As of 4/30/2005
PERFORMANCE SUMMARY
All of the returns in this report represent past performance, which is not a guarantee of future results that may be achieved by the fund. (For performance data current to the most recent month-end, which may be higher or lower than that cited, visit our website at www.vanguard.com.) Note, too, that both investment returns and principal value can fluctuate widely, so an investor's shares, when sold, could be worth more or less than their original cost.
The returns shown do not reflect taxes that a shareholder would pay on fund distributions or on the sale of fund shares.


WINDSOR II FUND


Fiscal-Year Total Returns (%) October 31, 1994–April 30, 2005

Fiscal-Year Total Returns (%)

*Six months ended April 30, 2005.
Note: See Financial Highlights tables on pages 18 and 19 for dividend and capital gains information.



Average Annual Total Returns for periods ended March 31, 2005

This table presents average annual total returns through the latest calendar quarter—rather than through the end of the fiscal period. Securities and Exchange Commission rules require that we provide this information.



One Five Ten Years
Inception Date Year Years Capital Income Total

Windsor II Fund            
  Investor Shares 6/24/1985  13.31% 7.71% 10.15% 2.53% 12.68%
  Admiral Shares 5/14/2001  13.43    4.85*   —  —  — 

*Return since inception





9


As of 4/30/2005
     FINANCIAL STATEMENTS (UNAUDITED)

STATEMENT OF NET ASSETS

This Statement provides a detailed list of the fund’s holdings, including each security’s market value on the last day of the reporting period. Securities are grouped and subtotaled by asset type (common stocks, bonds, etc.) and by industry sector. Other assets are added to, and liabilities are subtracted from, the value of Total Investments to calculate the fund’s Net Assets. Finally, Net Assets are divided by the outstanding shares of the fund to arrive at its share price, or Net Asset Value (NAV) Per Share.

At the end of the Statement of Net Assets, you will find a table displaying the composition of the fund’s net assets. Because all income and any realized gains must be distributed to shareholders each year, the bulk of net assets consists of Paid-in Capital (money invested by shareholders). The amounts shown for Undistributed Net Investment Income and Accumulated Net Realized Gains usually approximate the sums the fund had available to distribute to shareholders as income dividends or capital gains as of the statement date, but may differ because certain investments or transactions may be treated differently for financial statement and tax purposes. Any Accumulated Net Realized Losses, and any cumulative excess of distributions over net income or net realized gains, will appear as negative balances. Unrealized Appreciation (Depreciation) is the difference between the market value of the fund’s investments and their cost, and reflects the gains (losses) that would be realized if the fund were to sell all of its investments at their statement-date values.

The fund provides a complete list of its holdings four times in each fiscal year, at the quarter-ends. For the second and fourth fiscal quarters, the lists appear in the fund’s semiannual and annual reports to shareholders. For the first and third fiscal quarters, the fund files the lists with the Securities and Exchange Commission on Form N-Q. Shareholders can look up the fund’s Forms N-Q on the SEC’s website at www.sec.gov. Forms N-Q may also be reviewed and copied at the SEC’s Public Reference Room (see the back cover of this report for further information).



Windsor II Fund Shares Market
Value^
(000)

COMMON STOCKS (94.1%)**



Auto & Transportation (0.7%)    
Union Pacific Corp. 2,359,200  $150,824 
CSX Corp. 1,574,100  63,169 
Burlington Northern
Santa Fe Corp. 347,200  16,752 
Norfolk Southern Corp. 506,000  15,888 
Ford Motor Co. 1,100,853  10,029 
General Motors Corp. 318,068  8,486 
Lear Corp. 106,400  3,606 

     268,754 

Consumer Discretionary (9.3%)
Cendant Corp. 37,455,900  745,747 
(1) Mattel, Inc. 26,023,400  469,722 
Wal-Mart Stores, Inc. 7,585,800  357,595 
Gannett Co., Inc. 4,330,400  333,441 
* Time Warner, Inc. 13,096,494  220,152 
The Walt Disney Co. 7,825,232  206,586 
(1) Service Corp. International 26,080,100  183,604 
Carnival Corp. 3,649,600  178,392 
Eastman Kodak Co. 6,445,900  161,147 
Federated Department
Stores, Inc. 2,426,900  139,546 
* Sears Holdings Corp. 994,026  134,432 
* MGM Mirage, Inc. 578,000  40,350 
McDonald's Corp. 1,352,600  39,645 
Waste Management, Inc. 1,196,100  34,077 
Viacom Inc. Class B 935,601  32,391 
* Interpublic Group of Cos., Inc. 1,537,700  19,775 
Kimberly-Clark Corp. 305,200  19,060 
Yum! Brands, Inc. 384,000  18,033 
Limited Brands, Inc. 653,200  14,168 
VF Corp. 234,500  13,270 
Knight Ridder 177,600  11,491 
J.C. Penney Co., Inc.
(Holding Co.) 196,200  9,302 
Starwood Hotels &
Resorts Worldwide, Inc. 158,600  8,618 

10




Shares Market
Value^
(000)



Nordstrom, Inc. 146,600  $7,452 
ServiceMaster Co. 553,700  7,104 
* AutoNation, Inc. 283,400  5,178 
Regal Entertainment Group
Class A 130,900  2,656 
* Caesars Entertainment, Inc. 120,900  2,412 
* PHH Corp. 87,130  1,947 
Hearst-Argyle Television Inc. 68,400  1,717 
Belo Corp. Class A 60,116  1,409 
Sabre Holdings Corp. 71,300  1,395 
The McClatchy Co. Class A 1,500  106 

     3,421,920 

Consumer Staples (9.4%)
Altria Group, Inc. 14,165,700  920,629 
Imperial Tobacco Group ADR 12,840,000  744,848 
ConAgra Foods, Inc. 19,678,300  526,395 
PepsiCo, Inc. 5,678,300  315,941 
Anheuser-Busch Cos., Inc. 5,263,400  246,696 
The Coca-Cola Co. 5,589,799  242,821 
The Procter & Gamble Co. 2,387,500  129,283 
Sara Lee Corp. 5,209,200  111,425 
Albertson's, Inc. 2,942,961  58,241 
Kraft Foods Inc. 1,223,400  39,650 
Unilever PLC ADR 1,010,400  38,759 
* Safeway, Inc. 1,323,500  28,177 
Reynolds American Inc. 184,400  14,378 
General Mills, Inc. 283,600  14,010 
* Smithfield Foods, Inc. 289,500  8,760 
Tyson Foods, Inc. 410,300  6,930 
Carolina Group 176,500  5,560 
PepsiAmericas, Inc. 180,573  4,458 
SuperValu Inc. 19,302  609 

     3,457,570 

Financial Services (24.9%)
Banks—New York City (1.3%)
JPMorgan Chase & Co. 12,917,164  458,430 
The Bank of New York Co., Inc. 486,200  13,584 
Banks—Outside New York City (6.4%)
Wells Fargo & Co. 18,002,400  1,079,064 
Bank of America Corp. 18,829,115  848,063 
Wachovia Corp. 3,976,584  203,522 
Comerica, Inc. 638,800  36,578 
U.S. Bancorp 1,168,622  32,605 
KeyCorp 851,600  28,239 
UnionBanCal Corp. 379,174  23,342 
National City Corp. 496,200  16,851 
SunTrust Banks, Inc. 220,500  16,059 
BB&T Corp. 345,753  13,557 
Bank of Hawaii Corp. 274,314  12,989 
Huntington Bancshares Inc. 468,291  11,010 
Marshall & Ilsley Corp. 217,800  9,287 
PNC Financial Services Group 104,300  5,552 
Doral Financial Corp. 279,300  3,924 
Compass Bancshares Inc. 71,600  3,080 
Associated Banc-Corp. 34,617  1,070 
Diversified Financial Services (3.8%)
Citigroup, Inc. 19,197,873  901,532 
The Goldman Sachs Group, Inc. 2,341,800  250,081 
MetLife, Inc. 2,671,200  103,910 
American Express Co. 976,600  51,467 
Morgan Stanley 690,060  36,311 
CIT Group Inc. 758,800  30,564 
Merrill Lynch & Co., Inc. 486,400  26,232 
Marsh & McLennan Cos., Inc. 185,300  5,194 
Leucadia National Corp. 41,400  1,440 
Financial—Data Processing Services (0.8%)
Automatic Data Processing, Inc. 6,102,100  265,075 
Deluxe Corp. 308,100  12,302 
Financial—Miscellaneous (2.3%)
MBNA Corp. 26,848,600  530,260 
Freddie Mac 3,489,700  214,686 
Fannie Mae 671,800  36,244 
MBIA, Inc. 293,000  15,347 
* Providian Financial Corp. 842,000  14,036 
Nationwide Financial
Services, Inc. 305,500  10,824 
MGIC Investment Corp. 58,300  3,440 
Fidelity National Financial, Inc. 96,000  3,083 
Radian Group, Inc. 54,700  2,430 
Financial—Small Loan (1.7%)
SLM Corp. 12,841,500  611,769 
Insurance—Life (1.6%)
Manulife Financial Corp. 9,703,415  444,902 
Prudential Financial, Inc. 1,455,600  83,188 
The Principal
Financial Group, Inc. 1,208,600  47,232 
* Conseco, Inc. 910,400  17,516 
Insurance—Multiline (3.4%)
Allstate Corp. 12,842,844  721,254 
St. Paul Travelers Cos., Inc. 6,286,940  225,072 
The Hartford Financial
Services Group Inc. 2,512,327  181,817 

11




Windsor II Fund Shares Market
Value^
(000)



American International
Group, Inc. 485,000  $24,662 
Assurant, Inc. 587,000  19,424 
CIGNA Corp. 175,700  16,161 
SAFECO Corp. 297,800  15,685 
Genworth Financial Inc. 476,300  13,313 
Lincoln National Corp. 109,300  4,915 
Cincinnati Financial Corp. 92,725  3,731 
UnumProvident Corp. 169,200  2,829 
Protective Life Corp. 31,500  1,205 
Loews Corp. 15,200  1,077 
Insurance—Property-Casualty (1.1%)
XL Capital Ltd. Class A 5,230,600  367,711 
The Chubb Corp. 247,100  20,208 
W.R. Berkley Corp. 178,533  5,802 
Real Estate Investment Trusts (0.2%)
Simon Property Group, Inc. REIT 131,900  8,715 
Equity Office
Properties Trust REIT 252,400  7,943 
Equity Residential REIT 177,000  6,080 
Vornado Realty Trust REIT 71,700  5,481 
General Growth
Properties Inc. REIT 139,500  5,456 
ProLogis REIT 115,100  4,557 
Archstone-Smith Trust REIT 123,500  4,442 
Boston Properties, Inc. REIT 64,900  4,314 
Plum Creek Timber Co. Inc. REIT 114,900  3,969 
Kimco Realty Corp. REIT 59,600  3,301 
Avalonbay
Communities, Inc. REIT 45,200  3,254 
Public Storage, Inc. REIT 52,600  3,088 
Duke Realty Corp. REIT 89,200  2,730 
Developers Diversified
Realty Corp. REIT 64,100  2,720 
iStar Financial Inc. REIT 59,300  2,363 
Apartment Investment &
Management Co. Class A REIT 59,300  2,261 
The Macerich Co. REIT 37,100  2,237 
Regency Centers Corp. REIT 41,800  2,201 
Health Care Properties
Investors REIT 83,300  2,136 
Liberty Property Trust REIT 53,600  2,135 
AMB Property Corp. REIT 51,900  2,024 
Weingarten Realty
Investors REIT 52,900  1,905 
Hospitality
Properties Trust REIT 40,000  1,671 
New Plan Excel
Realty Trust REIT 64,200  1,657 
Friedman, Billings,
Ramsey Group, Inc. REIT 81,000  979 
Savings & Loan (2.2%)
Washington Mutual, Inc. 19,381,249  800,833 
Astoria Financial Corp. 105,000  2,784 
Securities Brokers & Services (0.1%)
Lehman Brothers Holdings, Inc. 181,900  16,684 
Bear Stearns Co., Inc. 147,500  13,962 
Countrywide Financial Corp. 361,736  13,091 

     9,095,710 

Health Care (11.7%)
Pfizer Inc. 34,128,945  927,283 
* WellPoint Inc. 4,824,400  616,317 
Schering-Plough Corp. 25,379,200  529,664 
Bristol-Myers Squibb Co. 18,150,900  471,923 
Wyeth 10,409,100  467,785 
Baxter International, Inc. 12,498,800  463,705 
Johnson & Johnson 3,953,100  271,301 
* Medco Health Solutions, Inc. 2,556,758  130,318 
* Triad Hospitals, Inc. 1,846,195  94,617 
Merck & Co., Inc. 2,493,900  84,543 
* Watson Pharmaceuticals, Inc. 2,663,523  79,906 
HCA Inc. 757,400  42,293 
Aetna Inc. 475,400  34,880 
Abbott Laboratories 541,900  26,640 
* Tenet Healthcare Corp. 2,087,000  24,981 
* Health Net Inc. 639,000  21,745 

     4,287,901 

Integrated Oils (10.4%)
Occidental Petroleum Corp. 15,829,600  1,092,242 
ConocoPhillips Co. 9,693,334  1,016,346 
BP PLC ADR 12,009,272  731,365 
ChevronTexaco Corp. 13,497,086  701,848 
ExxonMobil Corp. 4,037,594  230,264 
Petro-Canada 366,300  20,322 
Amerada Hess Corp. 134,899  12,633 
Unocal Corp. 176,900  9,650 
Marathon Oil Corp. 120,500  5,612 

     3,820,282 

Other Energy (1.0%)
Williams Cos., Inc. 8,576,700  145,975 
* Reliant Energy, Inc. 11,330,343  115,230 
Valero Energy Corp. 697,500  47,800 
Anadarko Petroleum Corp. 287,800  21,021 
Devon Energy Corp. 232,762  10,514 

12




Shares Market
Value^
(000)



Apache Corp. 158,570  $8,926 
* NRG Energy 252,119  7,841 
Kerr-McGee Corp. 88,300  6,852 
Noble Energy, Inc. 69,800  4,476 
Sunoco, Inc. 44,500  4,417 
Premcor, Inc. 38,600  2,553 

     375,605 

Materials & Processing (2.7%)
(1) Hanson PLC ADR 7,826,950  360,196 
Alcoa Inc. 5,224,500  151,615 
International Paper Co. 4,287,900  147,032 
MeadWestvaco Corp. 3,900,913  114,882 
Weyerhaeuser Co. 564,500  38,730 
Dow Chemical Co. 668,100  30,686 
E.I. du Pont de Nemours & Co. 547,787  25,806 
* The Mosaic Co. 1,497,800  19,247 
PPG Industries, Inc. 249,900  16,881 
Georgia Pacific Group 405,900  13,910 
Nucor Corp. 253,000  12,928 
Masco Corp. 361,100  11,371 
Bunge Ltd. 173,594  9,860 
Monsanto Co. 148,200  8,687 
Eastman Chemical Co. 150,200  8,111 
Phelps Dodge Corp. 74,700  6,413 
Archer-Daniels-Midland Co. 322,600  5,804 
United States Steel Corp. 100,300  4,289 
Rohm & Haas Co. 87,200  3,807 
Ashland, Inc. 36,000  2,421 
* Owens-Illinois, Inc. 92,300  2,263 
Lafarge North America Inc. 29,600  1,643 

     996,582 

Producer Durables (5.9%)
Emerson Electric Co. 7,421,900  465,130 
Nokia Corp. ADR 27,551,300  440,270 
The Boeing Co. 7,110,300  423,205 
(1) Cooper Industries, Inc. Class A 4,650,800  296,070 
United Technologies Corp. 1,635,200  166,333 
Northrop Grumman Corp. 2,905,500  159,338 
Centex Corp. 1,243,200  71,758 
Lockheed Martin Corp. 818,300  49,875 
Pulte Homes, Inc. 353,600  25,265 
Parker Hannifin Corp. 216,300  12,965 
Lennar Corp. Class A 232,600  11,972 
Ingersoll-Rand Co. 102,600  7,887 
D. R. Horton, Inc. 234,933  7,165 
Pitney Bowes, Inc. 140,300  6,274 
* Xerox Corp. 451,500  5,982 
Deere & Co. 46,200  2,889 
W.W. Grainger, Inc. 45,700  2,527 

     2,154,905 

Technology (4.3%)
International Business
Machines Corp. 3,985,100  304,382 
Microsoft Corp. 11,210,200  283,618 
Hewlett-Packard Co. 12,584,872  257,612 
Electronic Data
Systems Corp. 12,430,495  240,530 
Motorola, Inc. 12,272,600  188,262 
Computer Associates
International, Inc. 3,492,200  93,940 
* Nortel Networks Corp. 26,184,200  65,199 
* Freescale Semiconductor Inc.
Class A 2,428,700  45,465 
Raytheon Co. 1,086,800  40,875 
* Computer Sciences Corp. 336,300  14,622 
General Dynamics Corp. 106,600  11,198 
* Micron Technology, Inc. 1,102,700  10,707 
* Ingram Micro, Inc. Class A 517,300  8,618 
Scientific-Atlanta, Inc. 155,000  4,740 
* Freescale Semiconductor, Inc.
Class B 184,457  3,479 
National Semiconductor Corp. 168,000  3,205 
* Flextronics International Ltd. 237,300  2,646 
* Storage Technology Corp. 87,500  2,433 
* Lucent Technologies, Inc. 838,000  2,036 
* Compuware Corp. 225,100  1,339 
Applera Corp.-Applied
Biosystems Group 60,600  1,285 
Seagate Technology 53,000  932 

     1,587,123 

Utilities (9.4%)
Duke Energy Corp. 20,575,600  600,602 
Entergy Corp. 8,096,200  593,451 
American Electric
Power Co., Inc. 15,611,917  549,852 
Exelon Corp. 10,564,700  522,953 
Verizon Communications Inc. 14,252,354  510,234 
(1) CenterPoint Energy Inc. 22,781,700  269,735 
FirstEnergy Corp. 2,366,000  102,968 
FPL Group, Inc. 1,723,800  70,366 
SBC Communications Inc. 2,074,949  49,384 
BellSouth Corp. 1,146,400  30,368 
ALLTEL Corp. 290,800  16,564 
Sempra Energy 399,300  16,124 
Dominion Resources, Inc. 213,700  16,113 
PPL Corp. 259,200  14,064 
Pinnacle West Capital Corp. 303,600  12,721 
Southern Co. 352,700  11,621 
Edison International 265,200  9,627 
PG&E Corp. 264,000  9,166 
AT&T Corp. 470,469  9,000 

13




Windsor II Fund Shares Market
Value^
(000)



Xcel Energy, Inc. 434,200  $7,460 
CenturyTel, Inc. 209,100  6,417 
Wisconsin Energy Corp. 139,400  4,915 
Citizens Communications Co. 207,400  2,644 
Pepco Holdings, Inc. 116,200  2,518 
Energy East Corp. 91,900  2,391 
TECO Energy, Inc. 129,300  2,148 
Progress Energy, Inc. 41,000  1,722 
MDU Resources Group, Inc. 55,200  1,492 
KeySpan Corp. 13,200  501 
* U.S. Cellular Corp. 3,300  152 

     3,447,273 

Other (4.4%)
General Electric Co. 16,559,700  599,461 
Tyco International Ltd. 18,897,800  591,690 
ITT Industries, Inc. 4,050,500  366,408 
3M Co. 334,800  25,602 
Honeywell International Inc. 511,388  18,287 
Textron, Inc. 99,600  7,505 
Eaton Corp. 73,400  4,305 

     1,613,258 


TOTAL COMMON STOCKS
(Cost $25,822,024)    34,526,883 

TEMPORARY INVESTMENTS (6.8%)**

Exchange-Traded Funds (3.0%)
Vanguard Index Participation
Equity Receipts—
Total Stock Market 8,407,600  944,426 
Value 2,681,500  143,165 

     1,087,591 

Money Market Funds (3.8%)
Vanguard Market Liquidity
Fund, 2.829%† 1,245,884,515  1,245,885 
Vanguard Market Liquidity
Fund, 2.829%†—Note G 139,939,600  139,940 

     1,385,825 


  Face  Market 
  Amount  Value^ 
  (000) (000)

U.S. Agency Obligation (0.0%)
Federal Home Loan Mortgage Corp.††
(2) 3.002%, 7/19/2005 $33,000  $32,786 

TOTAL TEMPORARY INVESTMENTS
(Cost $2,432,879)    2,506,202 

TOTAL INVESTMENTS (100.9%)
(Cost $28,254,903)    37,033,085 

OTHER ASSETS AND
LIABILITIES—NET (-0.9%)    (328,528)

NET ASSETS (100%)    $36,704,557 

^ See Note A in Notes to Financial Statements.
* Non-income-producing security.
** The fund invests a portion of its cash reserves in equity markets through the use of index futures contracts and exchange-traded funds. After giving effect to these investments, the fund's effective common stock and temporary cash investment positions represent 97.8% and 3.1%, respectively, of net assets. See Note E in Notes to Financial Statements.
Money market fund available only to Vanguard funds and certain trusts and accounts managed by Vanguard. Rate shown is the 7-day yield.
†† The issuer operates under a congressional charter; its securities are neither issued nor guaranteed by the U.S. government. If needed, access to additional funding from the U.S. Treasury (beyond the issuer's line of credit) would require congressional action.
(1) Considered an affiliated company of the fund as the fund owns more than 5% of the outstanding voting securities of such company. See Note I in Notes to Financial Statements.
(2) Securities with a value of $32,786,000 have been segregated as initial margin for open futures contracts.
ADR--American Depositary Receipt.
REIT--Real Estate Investment Trust.

14




Market
Value^
(000)

STATEMENT OF ASSETS AND LIABILITIES  
Assets
  Investment in Securities, at Value $37,033,085 
  Receivables for Investment
    Securities Sold 37,441 
  Receivables for Capital Shares Issued 37,927 
  Other Assets—Note C 76,104 

    Total Assets 37,184,557 

Liabilities
  Security Lending Collateral
    Payable to Brokers—Note G 139,940 
  Payables for Investment
    Securities Purchased 263,870 
  Other Liabilities 76,190 

    Total Liabilities 480,000 


NET ASSETS (100%) $36,704,557 




Amount
(000)

AT APRIL 30, 2005, NET ASSETS CONSISTED OF:

Paid-in Capital $27,658,134 
Undistributed Net Investment Income 215,279 
Accumulated Net Realized Gains 57,112 
Unrealized Appreciation (Depreciation)
  Investment Securities 8,778,182 
  Futures Contracts (4,150)

NET ASSETS $36,704,557 

Investor Shares—Net Assets
Applicable to 995,867,370 outstanding $.001
  par value shares of beneficial interest
  (unlimited authorization) $30,408,870 

NET ASSET VALUE PER SHARE—
  INVESTOR SHARES $30.54 

Admiral Shares—Net Assets
Applicable to 116,106,864 outstanding $.001
  par value shares of beneficial interest
  (unlimited authorization) $6,295,687 

NET ASSET VALUE PER SHARE—
  ADMIRAL SHARES $54.22 

See Note E in Notes to Financial Statements for the tax-basis components of net assets.


15


STATEMENT OF OPERATIONS

This Statement shows the types of income earned by the fund during the reporting period, and details the operating expenses charged to each class of its shares. These expenses directly reduce the amount of investment income available to pay to shareholders as income dividends. This Statement also shows any Net Gain (Loss) realized on the sale of investments, and the increase or decrease in the Unrealized Appreciation (Depreciation) of investments during the period.



Windsor II Fund
Six Months Ended April 30, 2005
(000)

INVESTMENT INCOME  
Income
  Dividends* $432,093 
  Interest 14,060 
  Security Lending 837 

    Total Income 446,990 

Expenses
  Investment Advisory Fees—Note B
    Basic Fee 20,619 
    Performance Adjustment 1,372 
  The Vanguard Group—Note C
    Management and Administrative
      Investor Shares 30,257 
      Admiral Shares 2,678 
    Marketing and Distribution
      Investor Shares 1,675 
      Admiral Shares 344 
  Custodian Fees 213 
  Shareholders' Reports
    Investor Shares 313 
    Admiral Shares
  Trustees' Fees and Expenses 31 

    Total Expenses 57,505 
    Expenses Paid Indirectly—Note D (3,557)

    Net Expenses 53,948 

NET INVESTMENT INCOME 393,042 

REALIZED NET GAIN (LOSS)
  Investment Securities Sold* 1,326,487 
  Futures Contracts 14,387 

REALIZED NET GAIN (LOSS) 1,340,874 

CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION)
  Investment Securities 853,115 
  Futures Contracts (9,148)

CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION) 843,967 

NET INCREASE (DECREASE) IN NET ASSETS RESULTING FROM OPERATIONS $2,577,883 

* Dividend income and realized net gain (loss) from affiliated companies of the fund were $29,790,000 and $49,306,000, respectively. See Note I in Notes to Financial Statements.

16


STATEMENT OF CHANGES IN NET ASSETS

This Statement shows how the fund’s total net assets changed during the two most recent reporting periods. The Operations section summarizes information detailed in the Statement of Operations. The amounts shown as Distributions to shareholders from the fund’s net income and capital gains may not match the amounts shown in the Operations section, because distributions are determined on a tax basis and may be made in a period different from the one in which the income was earned or the gains were realized on the financial statements. The Capital Share Transactions section shows the net amount shareholders invested in or redeemed from the fund. Distributions and Capital Share Transactions are shown separately for each class of shares.



Windsor II Fund
Six Months
Ended
April 30, 2005
(000)
Year
Ended
Oct. 31, 2004
(000)

INCREASE (DECREASE) IN NET ASSETS    
Operations
  Net Investment Income $393,042  $588,191 
  Realized Net Gain (Loss) 1,340,874  524,658 
  Change in Unrealized Appreciation (Depreciation) 843,967  3,388,052 

    Net Increase (Decrease) in Net Assets Resulting from Operations 2,577,883  4,500,901 

Distributions
  Net Investment Income
    Investor Shares (291,064) (477,750)
    Admiral Shares (56,343) (85,900)
  Realized Capital Gain
    Investor Shares —  — 
    Admiral Shares —  — 

    Total Distributions (347,407) (563,650)

Capital Share Transactions—Note H
  Investor Shares 2,292,631  2,021,262 
  Admiral Shares 1,100,716  867,039 

    Net Increase (Decrease) from Capital Share Transactions 3,393,347  2,888,301 

  Total Increase (Decrease) 5,623,823  6,825,552 

Net Assets
  Beginning of Period 31,080,734  24,255,182 

  End of Period $36,704,557  $31,080,734 




17


FINANCIAL HIGHLIGHTS

This table summarizes the fund’s investment results and distributions to shareholders on a per-share basis for each class of shares. It also presents the Total Return and shows net investment income and expenses as percentages of average net assets. These data will help you assess: the variability of the fund’s net income and total returns from year to year; the relative contributions of net income and capital gains to the fund’s total return; how much it costs to operate the fund; and the extent to which the fund tends to distribute capital gains. The table also shows the Portfolio Turnover Rate, a measure of trading activity. A turnover rate of 100% means that the average security is held in the fund for one year.


Windsor II Fund Investor Shares
Six Months
Ended
Year Ended October 31,
For a Share Outstanding Throughout Each Period April 30, 2005 2004 2003 2002 2001 2000

Net Asset Value, Beginning of Period $28.49  $24.61  $20.87  $24.50  $27.58  $29.03 

Investment Operations
  Net Investment Income .33  .56  .51  .51  .564  .64 
  Net Realized and Unrealized Gain (Loss)
    on Investments 2.03  3.87  3.75  (3.47) (1.819) 1.08 

    Total from Investment Operations 2.36  4.43  4.26  (2.96) (1.255) 1.72 

Distributions
  Dividends from Net Investment Income (.31) (.55) (.52) (.52) (.585) (.67)
  Distributions from Realized Capital Gains —  —  —  (.15) (1.240) (2.50)

    Total Distributions (.31) (.55) (.52) (.67) (1.825) (3.17)

Net Asset Value, End of Period $30.54  $28.49  $24.61  $20.87  $24.50  $27.58 

Total Return 8.28% 18.15% 20.68% -12.51%  -4.89%  7.22%

Ratios/Supplemental Data
  Net Assets, End of Period (Millions) $30,409  $26,232  $20,843  $17,735  $21,495  $24,070 
  Ratio of Total Expenses to Average Net Assets* 0.35%** 0.37% 0.43% 0.42% 0.40% 0.37%
  Ratio of Net Investment Income to
    Average Net Assets 2.26%** 2.07% 2.31% 2.12% 2.10% 2.36%
  Portfolio Turnover Rate 30%** 22% 29% 41% 33% 26%

Includes performance-based investment advisory fee increases (decreases) of 0.01%, 0.02%, 0.03%, 0.02%, 0.00%, and (0.03%).
**  Annualized.

18



Windsor II Fund Admiral Shares
Six Months
Ended
Year Ended
October 31,

May14* to
Oct. 31,
For a Share Outstanding Throughout Each Period April 30, 2005 2004 2003 2002 2001

Net Asset Value, Beginning of Period $50.59  $43.69  $37.05  $43.50  $50.00 

Investment Operations
  Net Investment Income .622  1.043  .95  .944  .408 
  Net Realized and Unrealized Gain (Loss) on Investments 3.585  6.885  6.65  (6.167) (6.433)

    Total from Investment Operations 4.207  7.928  7.60  (5.223) (6.025)

Distributions
  Dividends from Net Investment Income (.577) (1.028) (.96) (.962) (.475)
  Distributions from Realized Capital Gains —  —  —  (.265) — 

    Total Distributions (.577) (1.028) (.96) (1.227) (.475)

Net Asset Value, End of Period $54.22  $50.59  $43.69  $37.05  $43.50 

Total Return 8.31% 18.30% 20.79% -12.44%  -12.16% 

Ratios/Supplemental Data
  Net Assets, End of Period (Millions) $6,296  $4,849  $3,412  $2,484  $2,039 
  Ratio of Total Expenses to Average Net Assets** 0.24%† 0.26% 0.32% 0.35% 0.35%†
  Ratio of Net Investment Income to Average Net Assets 2.36%† 2.17% 2.41% 2.18% 1.83%†
  Portfolio Turnover Rate 30%† 22% 29% 41% 33%

* Inception.
** Includes performance-based investment advisory fee increases (decreases) of 0.01%, 0.02%, 0.03%, 0.02%, and 0.00%.
Annualized.





SEE ACCOMPANYING NOTES, WHICH ARE AN INTEGRAL PART OF THE FINANCIAL STATEMENTS.

19


NOTES TO FINANCIAL STATEMENTS

Vanguard Windsor II Fund is registered under the Investment Company Act of 1940 as an open-end investment company, or mutual fund. The fund offers two classes of shares, Investor Shares and Admiral Shares. Investor Shares are available to any investor who meets the fund’s minimum purchase requirements. Admiral Shares are designed for investors who meet certain administrative, servicing, tenure, and account-size criteria.

A. The following significant accounting policies conform to generally accepted accounting principles for U.S. mutual funds. The fund consistently follows such policies in preparing its financial statements.

1. Security Valuation: Securities are valued as of the close of trading on the New York Stock Exchange (generally 4:00 p.m. Eastern time) on the valuation date. Equity securities are valued at the latest quoted sales prices or official closing prices taken from the primary market in which each security trades; such securities not traded on the valuation date are valued at the mean of the latest quoted bid and asked prices. Securities for which market quotations are not readily available, or whose values have been materially affected by events occurring before the fund’s pricing time but after the close of the securities’ primary markets, are valued by methods deemed by the board of trustees to represent fair value. Investments in Vanguard Market Liquidity Fund are valued at that fund’s net asset value. Temporary cash investments acquired over 60 days to maturity are valued using the latest bid prices or using valuations based on a matrix system (which considers such factors as security prices, yields, maturities, and ratings), both as furnished by independent pricing services. Other temporary cash investments are valued at amortized cost, which approximates market value.

2. Futures Contracts: The fund uses S&P 500 Index futures contracts to a limited extent, with the objective of maintaining full exposure to the stock market while maintaining liquidity. The fund may purchase or sell futures contracts to achieve a desired level of investment, whether to accommodate portfolio turnover or cash flows from capital share transactions. The primary risks associated with the use of futures contracts are imperfect correlation between changes in market values of stocks held by the fund and the prices of futures contracts, and the possibility of an illiquid market.

Futures contracts are valued at their quoted daily settlement prices. The aggregate principal amounts of the contracts are not recorded in the financial statements. Fluctuations in the value of the contracts are recorded in the Statement of Net Assets as an asset (liability) and in the Statement of Operations as unrealized appreciation (depreciation) until the contracts are closed, when they are recorded as realized futures gains (losses).

3. Federal Income Taxes: The fund intends to continue to qualify as a regulated investment company and distribute all of its taxable income. Accordingly, no provision for federal income taxes is required in the financial statements.

4. Distributions: Distributions to shareholders are recorded on the ex-dividend date.

5. Security Lending: The fund may lend its securities to qualified institutional borrowers to earn additional income. Security loans are required to be secured at all times by collateral at least equal to the market value of securities loaned. The fund invests cash collateral received in Vanguard Market Liquidity Fund, and records a liability for the return of the collateral, during the period the securities are on loan. Security lending income represents the income earned on investing cash collateral, less expenses associated with the loan.

6. Other: Dividend income is recorded on the ex-dividend date. Interest income includes income distributions received from Vanguard Market Liquidity Fund and is accrued daily. Security transactions are accounted for on the date securities are bought or sold. Costs used to determine realized gains (losses) on the sale of investment securities are those of the specific securities sold.

  Each class of shares has equal rights as to assets and earnings, except that each class separately bears certain class-specific expenses related to maintenance of shareholder accounts (included in Management and Administrative expenses) and shareholder reporting. Marketing and distribution expenses are allocated to each class of shares based on a method approved by the board of trustees. Income, other non-class-specific expenses, and gains and losses on investments are allocated to each class of shares based on its relative net assets.

20


B. Barrow, Hanley, Mewhinney & Strauss, Inc.; Equinox Capital Management, LLC; Tukman Capital Management, Inc.; and, Hotchkis and Wiley Capital Management, LLC, each provide investment advisory services to a portion of the fund for a fee calculated at an annual percentage rate of average net assets managed by the advisor. The basic fees of Barrow, Hanley, Mewhinney & Strauss, Inc., Equinox Capital Management, LLC, and Tukman Capital Management, Inc., are subject to quarterly adjustments based on performance for the preceding three years relative to a designated market index: for Barrow, Hanley, Mewhinney & Strauss, Inc., the S&P 500/Barra Value Index; for Equinox Capital Management, LLC, the Russell 1000 Value Index, and for Tukman Capital Management, Inc., the S&P 500 Index. The basic fee of Hotchkis and Wiley Capital Management, LLC is subject to quarterly adjustments based on performance since November 1, 2004, relative to the MSCI US Investable Market 2500 Index.

The Vanguard Group provides investment advisory services to a portion of the fund on an at-cost basis; the fund paid Vanguard advisory fees of $409,000 for the six months ended April 30, 2005.

For the six months ended April 30, 2005, the aggregate investment advisory fee represented an effective annual basic rate of 0.12% of the fund’s average net assets before an increase of $1,372,000 (0.01%) based on performance.

C. The Vanguard Group furnishes at cost corporate management, administrative, marketing, and distribution services. The costs of such services are allocated to the fund under methods approved by the board of trustees. The fund has committed to provide up to 0.40% of its net assets in capital contributions to Vanguard. At April 30, 2005, the fund had contributed capital of $4,725,000 to Vanguard (included in Other Assets), representing 0.01% of the fund’s net assets and 4.72% of Vanguard’s capitalization. The fund’s trustees and officers are also directors and officers of Vanguard.

D. The fund has asked its investment advisors to direct certain security trades, subject to obtaining the best price and execution, to brokers who have agreed to rebate to the fund part of the commissions generated. Such rebates are used solely to reduce the fund’s management and administrative expenses. The fund’s custodian bank has also agreed to reduce its fees when the fund maintains cash on deposit in the non-interest-bearing custody account. For the six months ended April 30, 2005, these arrangements reduced the fund’s management and administrative expenses by $3,555,000 and custodian fees by $2,000. The total expense reduction represented an effective annual rate of 0.02% of the fund’s average net assets.

E. Distributions are determined on a tax basis and may differ from net investment income and realized capital gains for financial reporting purposes. Differences may be permanent or temporary. Permanent differences are reclassified among capital accounts in the financial statements to reflect their tax character. Temporary differences arise when certain items of income, expense, gain, or loss are recognized in different periods for financial statement and tax purposes; these differences will reverse at some time in the future. Differences in classification may also result from the treatment of short-term gains as ordinary income for tax purposes.

The fund’s tax-basis capital gains and losses are determined only at the end of each fiscal year. For tax purposes, at October 31, 2004, the fund had available realized losses of $1,270,148,000 to offset future net capital gains of $401,220,000 through October 31, 2010, and $868,928,000 through October 31, 2011. The fund will use these capital losses to offset net taxable capital gains, if any, realized during the year ending October 31, 2005; should the fund realize net capital losses for the year, the losses will be added to the loss carryforward balances above.

At April 30, 2005, net unrealized appreciation of investment securities for tax purposes was $8,778,182,000, consisting of unrealized gains of $9,630,324,000 on securities that had risen in value since their purchase and $852,142,000 in unrealized losses on securities that had fallen in value since their purchase.

21


NOTES TO FINANCIAL STATEMENTS (CONTINUED)

At April 30, 2005, the aggregate settlement value of open futures contracts expiring in June 2005 and the related unrealized appreciation (depreciation) were:



(000)
Futures Contracts Number of
Long Contracts
Aggregate
Settlement
Value
Unrealized
Appreciation
(Depreciation)

E-mini S&P 500 Index 2,981  $172,675  $5 
S&P 500 Index 418  121,063  (4,155)

Unrealized appreciation (depreciation) on open futures contracts is required to be treated as realized gain (loss) for tax purposes.

F. During the six months ended April 30, 2005, the fund purchased $8,420,090,000 of investment securities and sold $5,041,162,000 of investment securities, other than temporary cash investments.

G. The market value of securities on loan to broker/dealers at April 30, 2005, was $134,404,000 for which the fund received cash collateral of $139,940,000.

H. Capital share transactions of each class of shares were:



Six Months Ended
April 30, 2005

Year Ended
October 31, 2004

Amount
(000)
Shares
(000)
Amount
(000)
Shares
(000)

Investor Shares          
  Issued $3,961,970  129,819    $4,036,083  147,462 
  Issued in Lieu of Cash Distributions 280,075  9,141    455,769  16,962 
  Redeemed (1,949,414) (63,859)   (2,470,590) (90,679)

    Net Increase (Decrease)—Investor Shares 2,292,631  75,101    2,021,262  73,745 

Admiral Shares
  Issued 1,368,617  25,219    1,303,621  26,789 
  Issued in Lieu of Cash Distributions 51,064  939    77,428  1,621 
  Redeemed (318,965) (5,903)   (514,010) (10,659)

    Net Increase (Decrease)—Admiral Shares 1,100,716  20,255    867,039  17,751 

22


I. Certain of the fund’s investments are in companies that are considered to be affiliated companies of the fund because the fund owns more than 5% of the outstanding voting securities of the company. Transactions during the period in securities of affiliated companies were as follows:



(000)
Current Period Transactions
Oct. 31, 2004
Market
Value
Purchases
at Cost
Proceeds from
Securities
Sold
Dividend
Income
Apr. 30, 2005
Market
Value

CenterPoint Energy Inc. $249,353  —  $10,352  $6,929  $269,735 
Cooper Industries, Inc. Class A 297,186  —  —  3,348  296,070 
Hanson PLC ADR 288,814  —  —  9,661  360,196 
Mattel, Inc. n/a*  $179,552  —  9,200  469,722 
Reliant Energy, Inc. 181,861  —  80,448  —  n/a** 
Service Corp. International 172,389  —  —  652  183,604 


  $1,189,603        $29,790  $1,579,327 



* At October 31, 2004, the issuer was not an affiliated company of the fund.
** At April 30, 2005, the security is still held but the issuer is no longer an affiliated company of the fund.

23



       ABOUT YOUR FUND’S EXPENSES


As a shareholder of the fund, you incur ongoing costs, which include costs for portfolio management, administrative services, and shareholder reports (like this one), among others. Operating expenses, which are deducted from a fund’s gross income, directly reduce the investment return of the fund.
A fund’s expenses are expressed as a percentage of its average net assets. This figure is known as the expense ratio. The following examples are intended to help you understand the ongoing costs (in dollars) of investing in your fund and to compare these costs with those of other mutual funds. The examples are based on an investment of $1,000 made at the beginning of the period shown and held for the entire period.
The table below illustrates your fund’s costs in two ways:

Based on actual fund return. This section helps you to estimate the actual expenses that you paid over the period. The “Ending Account Value” shown is derived from the fund’s actual return, and the third column shows the dollar amount that would have been paid by an investor who started with $1,000 in the fund. You may use the information here, together with the amount you invested, to estimate the expenses that you paid over the period.

  To do so, simply divide your account value by $1,000 (for example, an $8,600 account value divided by $1,000 = 8.6), then multiply the result by the number given for your fund under the heading “Expenses Paid During Period.”

Based on hypothetical 5% yearly return. This section is intended to help you compare your fund’s costs with those of other mutual funds. It assumes that the fund had a yearly return of 5% before expenses, but that the expense ratio is unchanged. In this case—because the return used is not the fund’s actual return—the results do not apply to your investment. The example is useful in making comparisons because the Securities and Exchange Commission requires all mutual funds to calculate expenses based on a 5% return.

  You can assess your fund’s costs by comparing this hypothetical example with the hypothetical examples that appear in shareholder reports of other funds.


Six Months Ended April 30, 2005
Windsor II Fund Beginning
Account Value
10/31/2004
Ending
Account Value
4/30/2005
Expenses
Paid During
Period*

Based on Actual Fund Return
Investor Shares $1,000.00  $1,082.80  $1.81 
Admiral Shares 1,000.00  1,083.12  1.24 

Based on Hypothetical 5% Yearly Return
Investor Shares $1,000.00  $1,023.06  $1.76 
Admiral Shares 1,000.00  1,023.60  1.20 

* The calculations are based on expenses incurred in the most recent six-month period. The fund’s annualized six-month expense ratios for that period are 0.35% for Investor Shares and 0.24% for Admiral Shares. The dollar amounts shown as “Expenses Paid” are equal to the annualized expense ratio multiplied by the average account value over the period, multiplied by the number of days in the most recent six-month period, then divided by the number of days in the most recent 12-month period.

Note that the expenses shown in the adjacent table are meant to highlight and help you compare ongoing costs only and do not reflect any transactional costs or account maintenance fees. They do not include your fund’s low-balance fee, which is described in the prospectus. If this fee were applied to your account, your costs would be higher. Your fund does not charge transaction fees, such as purchase or redemption fees, nor does it carry a “sales load.”

The calculations assume no shares were bought or sold during the period. Your actual costs may have been higher or lower, depending on the amount of your investment and the timing of any purchases or redemptions.

You can find more information about the fund’s expenses, including annual expense ratios, in the Financial Statements section of this report. For additional information on operating expenses and other shareholder costs, please refer to the appropriate fund prospectus.

24



       TRUSTEES RENEW ADVISORY ARRANGEMENTS


The board of trustees of Vanguard Windsor II Fund has renewed investment advisory arrangements with Barrow, Hanley, Mewhinney & Strauss, Inc., Hotchkis and Wiley Capital Management, LLC, and The Vanguard Group, Inc., three of the fund’s investment advisors. The board determined that the retention of the three advisors was in the best interests of the fund and its shareholders. The board will review investment advisory agreements with Equinox Capital Management, LLC, and Tukman Capital Management, Inc., later in 2005.

The board considered each arrangement separately, deciding to renew each of them based upon its most recent evaluation of the advisor’s investment staff, portfolio management process, and performance. The trustees considered the factors discussed below, among others. However, no single factor determined whether the board approved the arrangements. Rather, it was the totality of the circumstances that drove the board’s decision.

NATURE, EXTENT, AND QUALITY OF SERVICES

The board considered the quality of investment management over both short- and long-term periods, and took into account the organizational depth and stability of each firm.

Barrow, Hanley, Mewhinney & Strauss, Inc. Barrow, Hanley’s portfolio management team has significant depth and experience. Lead manager James P. Barrow has more than 40 years of investment experience and is backed by a team of nine portfolio managers and six analysts specializing in mid- and large-capitalization value strategies. He has advised the fund since 1985. Barrow, Hanley has assets under management of approximately $46 billion.

Hotchkis and Wiley Capital Management, LLC. Hotchkis and Wiley’s portfolio management team has significant depth and experience, with a dedicated focus on value-oriented investing. Portfolio managers George H. Davis, Jr. and Sheldon J. Lieberman have 22 and 19 years of investment experience, respectively. They have advised the fund since 2003. Hotchkis and Wiley has assets under management of approximately $22 billion.

The Vanguard Group. Vanguard, through its Quantitative Equity Group, has been managing investments for more than two decades. George U. Sauter, Vanguard managing director and chief investment officer, has been in the investment management business since 1985 and oversees more than $580 billion in assets (stocks and bonds). The group adheres to a sound, disciplined investment management process; the team has considerable experience, stability, and depth.

INVESTMENT PERFORMANCE

The board considered the short- and long-term performance of the fund, including any periods of outperformance or underperformance of relevant benchmarks and peer groups. Each investment advisor has carried out its investment strategy in a disciplined fashion, and the results provided by each advisor have been in line with expectations. The fund outperformed the average returns of its peer group over one-, five-, and ten-year periods. Information about the fund’s performance, including some of the data considered by the board, can be found in the “Performance Summary” section of this report.

COST

Vanguard Windsor II Fund’s expense ratio was far below the average expense ratio charged by funds in the fund’s peer group. The fund’s advisory fees were also well below the peer-group average. Information about the fund’s expense ratio appears in the “About Your Fund’s Expenses” section of this report as well as in the “Financial Statements” section,

25


TRUSTEES RENEW ADVISORY ARRANGEMENTS (CONTINUED)


which also includes information about the advisory fee rate. The board did not consider profitability of the advisors in determining whether to approve the advisory fee. Barrow, Hanley and Hotchkis and Wiley are independent firms, and the advisory fee is the result of arm’s-length negotiations. The board does not consider a “profitability” analysis of Vanguard because of Vanguard’s unique “at-cost” structure. Unlike most other mutual fund management companies, Vanguard is owned by the funds it oversees, and only produces “profits” in the form of reduced expenses for fund shareholders.

THE BENEFIT OF ECONOMIES OF SCALE

The board concluded that the fund’s shareholders benefit from economies of scale because of breakpoints in the advisory fee schedule for Barrow, Hanley and Hotchkis and Wiley. The breakpoints reduce the effective rate of the fee as the fund’s assets managed by Barrow, Hanley and Hotchkis and Wiley increase. The board also concluded that the Windsor II Fund’s low-cost arrangement with Vanguard ensures that the fund will realize economies of scale as it grows, with the cost to shareholders declining as the fund’s assets managed by Vanguard increase.

The advisory arrangements with Barrow, Hanley, with Hotchkis and Wiley, and with Vanguard will continue for one year and are renewable by the fund’s board after that for successive one-year periods.







26



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27


THE PEOPLE WHO GOVERN YOUR FUND


The trustees of your mutual fund are there to see that the fund is operated and managed in your best interests since, as a shareholder, you are a part owner of the fund. Your fund trustees also serve on the board of directors of The Vanguard Group, Inc., which is owned by the Vanguard funds and provides services to them on an at-cost basis.

A majority of Vanguard's board members are independent, meaning that they have no affiliation with Vanguard or the funds they oversee, apart from the sizable personal investments they have made as private individuals.
 
Our independent board members bring distinguished backgrounds in business, academia, and public service to their task of working with Vanguard officers to establish the policies and oversee the activities of the funds. Among board members’ responsibilities are



Name
(Year of Birth)
Trustee/Officer
Since

Position(s) Held with
Fund (Number of
Vanguard Funds
Overseen by
Trustee/Officer)

Principal Occupation(s) During the Past Five Years
John J. Brennan*
(1954)
May 1987

Chairman of the
Board, Chief
Executive Officer,
and Trustee
(132)
Chairman of the Board,Chief Executive Officer, and Director/Trustee of The Vanguard Group, Inc., and of each of the investment companies served by The Vanguard Group.

INDEPENDENT TRUSTEES
Charles D. Ellis
(1937)
January 2001
Trustee
(132)
The Partners of `63 (pro bono ventures in education); Senior Advisor to Greenwich Associates (international business strategy consulting); Successor Trustee of Yale University; Overseer of the Stern School of Business at New York University; Trustee of the Whitehead Institute for Biomedical Research.

Rajiv L. Gupta
(1945)
December 2001**
Trustee
(132)
Chairman and Chief Executive Officer of Rohm and Haas Co. (chemicals); Board Member of the American Chemistry Council; Director of Tyco International, Ltd. (diversified manufacturing and services) (since 2005);Trustee of Drexel University and of the Chemical Heritage Foundation.

JoAnn Heffernan
Heisen

(1950)
July 1998
Trustee
(132)
Vice President, Chief Information Officer, and Member of the Executive Committee of Johnson & Johnson (pharmaceuticals/consumer products); Director of the University Medical Center at Princeton and Women's Research and Education Institute.

Burton G. Malkiel
(1932)
May 1977
Trustee
(129)
Chemical Bank Chairman's Professor of Economics, Princeton University; Director of Vanguard Investment Series plc (Irish investment fund) (since November 2001), Vanguard Group (Ireland) Limited (investment management) (since November 2001), BKF Capital (investment management), The Jeffrey Co. (holding company), and CareGain, Inc. (health care management).

André F. Perold
(1952)
December 2004
Trustee
(132)
George Gund Professor of Finance and Banking, Harvard Business School (since 2000); Senior Associate Dean, Director of Faculty Recruiting, and Chair of Finance Faculty, Harvard Business School; Director and Chairman of UNX, Inc. (equities trading firm) (since 2003); Director of registered investment companies advised by Merrill Lynch Investment Managers and affiliates (1985–2004), Genbel Securities Limited (South African financial services firm) (1999–2003), Gensec Bank (1999–2003), Sanlam Investment Management (1999–2001), Sanlam, Ltd. (South African insurance company) (2001–2003), Stockback, Inc. (credit card firm) (2000–2002), and Bulldogresearch.com (investment research) (1999–2001); and Trustee of Commonfund (investment management) (1989–2001).



selecting investment advisors for the funds; monitoring fund operations, performance, and costs; reviewing contracts; nominating and selecting new trustees/directors; and electing Vanguard officers.

Each trustee serves a fund until its termination; or until the trustee’s retirement, resignation, or death; or otherwise as specified in the fund’s organizational documents. Any trustee may be removed at a shareholders’ meeting by a vote representing two-thirds of the net asset value of all shares of the fund together with shares of other Vanguard funds organized within the same trust. The table on these two pages shows information for each trustee and executive officer of the fund. The mailing address of the trustees and officers is P.O. Box 876, Valley Forge, PA 19482.



Name
(Year of Birth)
Trustee/Officer
Since

Position(s) Held with
Fund (Number of
Vanguard Funds
Overseen by
Trustee/Officer)

Principal Occupation(s) During the Past Five Years
Alfred M. Rankin, Jr.
(1941)
January 1993
Trustee
(132)
Chairman, President, Chief Executive Officer, and Director of NACCO
Industries, Inc. (forklift trucks/housewares/lignite); Director of Goodrich Corporation (industrial products/aircraft systems and services); Director of Standard Products Company (supplier for the automotive industry) until 1998.

J. Lawrence Wilson
(1936)
April 1985
Trustee
(132)

Retired Chairman and Chief Executive Officer of Rohm and Haas Co. (chemicals); Director of Cummins Inc. (diesel engines), MeadWestvaco Corp. (packaging products), and AmerisourceBergen Corp. (pharmaceutical distribution); Trustee of Vanderbilt University and of Culver Educational Foundation.

EXECUTIVE OFFICERS*

R. Gregory Barton
(1951)
June 2001

Secretary
(132)

Managing Director and General Counsel of The Vanguard Group, Inc.; Secretary of The Vanguard Group, Inc. and of each of the investment
companies served by The Vanguard Group since June 2001.

Thomas J. Higgins
(1957)
July 1998
Treasurer
(132)
Principal of The Vanguard Group, Inc.; Treasurer of each of the investment companies served by The Vanguard Group.

* Officers of the funds are “interested persons” as defined in the Investment Company Act of 1940.
** December 2002 for Vanguard Equity Income Fund, Vanguard Growth Equity Fund, the Vanguard Municipal Bond Funds, and the Vanguard State Tax-Exempt Funds.

More information about the trustees is in the Statement of Additional Information, available from The Vanguard Group.




VANGUARD SENIOR MANAGEMENT TEAM

Mortimer J. Buckley, Information Technology.
James H. Gately, Investment Programs and Services.
Kathleen C. Gubanich, Human Resources.
F. William McNabb, III, Client Relationship Group.
Michael S. Miller, Planning and Development.
Ralph K. Packard, Finance.
George U. Sauter, Chief Investment Officer.



John C. Bogle, Founder; Chairman and Chief Executive Officer, 1974-1996.



The Vanguard Group (R)
Post Office Box 2600
Valley Forge, PA 19482-2600




Vanguard, The Vanguard Group, Vanguard.com, Admiral, PlainTalk, Windsor, and the ship logo are trademarks of The Vanguard Group, Inc.

All other marks are the exclusive property of their respective owners.

All comparative mutual fund data are from Lipper Inc. or Morningstar, Inc., unless otherwise noted.

For More Information
This report is intended for the funds' shareholders. It may not be distributed to prospective investors unless it is preceded or accompanied by the current fund prospectus. To receive a free copy of the prospectus or the Statement of Additional Information, or to request additional information about the funds or other Vanguard funds, please contact us at one of the adjacent telephone numbers or by e-mail through Vanguard.com. Prospectuses may also be viewed online.

You can obtain a free copy of Vanguard's proxy voting guidelines by visiting our website, www.vanguard.com, and searching for "proxy voting guidelines," or by calling Vanguard at 800-662-2739. They are also available from the SEC's website, www.sec.gov. In addition, you may obtain a free report on how the fund voted the proxies for securities it owned during the 12 months ended June 30. To get the report, visit either www.vanguard.com or www.sec.gov.

You can review and copy information about your fund at the SEC's Public Reference Room in Washington, D.C. To find out more about this public service, call the SEC at 202-942-8090. Information about your fund is also available on the SEC's website, and you can receive copies of this information, for a fee, by sending a request in either of two ways: via e-mail addressed to publicinfo@sec.gov or via regular mail addressed to the Public Reference Section, Securities and Exchange Commission, Washington, DC 20549-0102.
World Wide Web
www.vanguard.com

Fund Information
800-662-7447

Direct Investor
Account Services

800-662-2739

Institutional Investor
Services

800-523-1036

Text Telephone
800-952-3335




















© 2005 The Vanguard Group, Inc.
All rights reserved.
Vanguard Marketing
Corporation, Distributor.

Q732 062005



Item 2: Not Applicable

Item 3: Not Applicable

Item 4: Not Applicable

Item 5: Not applicable.

Item 6: Not applicable.

Item 7: Not applicable.

Item 8: Not applicable.

Item 9: Not applicable.

Item 10: Not applicable.

Item 11: Controls and Procedures

        (a) Disclosure Controls and Procedures. The Principal Executive and Financial Officers concluded that the Registrant's Disclosure Controls and Procedures are effective based on their evaluation of the Disclosure Controls and Procedures as of a date within 90 days of the filing date of this report.

        (b) Internal Control Over Financial Reporting. There were no significant changes in Registrant’s Internal Control Over Financial Reporting or in other factors that could significantly affect this control subsequent to the date of the evaluation, including any corrective actions with regard to significant deficiencies and material weaknesses.

Item 12: Exhibits.

        Certifications.

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

VANGUARD WINDSOR FUNDS

BY: (signature)
(HEIDI STAM)
JOHN J. BRENNAN*
CHIEF EXECUTIVE OFFICER

Date:   June 14, 2005

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, this report has been signed below by the following persons on behalf of the registrant and in the capacities and on the dates indicated.

VANGUARD WINDSOR FUNDS

BY: (signature)
(HEIDI STAM)
JOHN J. BRENNAN*
CHIEF EXECUTIVE OFFICER

Date:   June 14, 2005

VANGUARD WINDSOR FUNDS

BY: (signature)
(HEIDI STAM)
THOMAS J. HIGGINS*
TREASURER

Date:   June 14, 2005

*By Power of Attorney. Filed on December 20, 2004, see File Number 002-14336. Incorporated by Reference.