8-K

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, DC 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d)

of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): October 19, 2023

ALPINE INCOME PROPERTY TRUST, INC.

(Exact name of registrant as specified in its charter)

Maryland	Commission File Number 001-39143	84-2769895
(State or other jurisdiction of incorporation or organization)		(I.R.S. Employer Identification No.)

369 N. New York Avenue, Suite 201 Winter Park, Florida	32789
(Address of principal executive offices)	(Zip Code)

Registrant’s Telephone Number, including area code

(407) 904-3324

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐	Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐	Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐	Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐	Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities Registered Pursuant to Section 12(b) of the Act

Title of each class	Trading Symbol	Name of each exchange on which registered
Common Stock, $0.01 Par Value	PINE	NYSE

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company  ☒

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.  ☒

Item 2.02. Results of Operations and Financial Condition

On October 19, 2023, Alpine Income Property Trust, Inc., a Maryland corporation (the "Company"), issued an earnings press release and an investor presentation relating to the Company’s financial results for the quarter ended September 30, 2023. Copies of the press release and investor presentation are attached hereto as Exhibits 99.1 and 99.2, respectively, and are incorporated herein by reference.

The information in Item 2.02 of this Current Report, including Exhibits 99.1 and 99.2 is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, unless it is specifically incorporated by reference therein.

Item 7.01. Regulation FD Disclosure

On October 19, 2023, the Company issued an earnings press release and an investor presentation relating to the Company’s financial results for the quarter ended September 30, 2023. Copies of the press release and investor presentation are attached hereto as Exhibits 99.1 and 99.2, respectively, and are incorporated herein by reference.

The furnishing of these materials is not intended to constitute a representation that such furnishing is required by Regulation FD or other securities laws, or that the materials include material investor information that is not otherwise publicly available. In addition, the Company does not assume any obligation to update such information in the future.

The information in Item 7.01 of this Current Report, including Exhibits 99.1 and 99.2 is being furnished and shall not be deemed to be “filed” for purposes of Section 18 of the Exchange Act or otherwise subject to the liabilities of that Section. The information in this Current Report shall not be incorporated by reference into any registration statement or other document pursuant to the Securities Act or the Exchange Act, unless it is specifically incorporated by reference therein.

Item 9.01. Financial Statements and Exhibits

(d) Exhibits

99.1 Earnings Press Release dated October 19, 2023

99.2 Investor Presentation dated October 19, 2023

104 Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURES

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

Date: October 19, 2023

Alpine Income Property Trust, Inc.

By: /s/ Matthew M. Partridge

Senior Vice President, Chief Financial Officer and Treasurer

(Principal Financial Officer)

EX-99.1

3

Press Release

Contact:Matthew M. Partridge

Senior Vice President, Chief Financial Officer & Treasurer

(407) 904-3324

mpartridge@alpinereit.com

FOR IMMEDIATE RELEASE ALPINE INCOME PROPERTY TRUST REPORTS THIRD QUARTER 2023 OPERATING RESULTS

WINTER PARK, FL – October 19, 2023 – Alpine Income Property Trust, Inc. (NYSE: PINE) (the “Company”or “PINE”) today announced its operating results and earnings for the quarter ended September 30, 2023.

Select Highlights

◾ Reported Net Loss per diluted share attributable to the Company of ($0.05) for the quarter ended September 30, 2023.

◾ Reported FFO per diluted share of $0.37 for the quarter ended September 30, 2023, a decrease of 7.5% from the comparable prior year period.

◾ Reported AFFO per diluted share of $0.38 for the quarter ended September 30, 2023, a decrease of 9.5% from the comparable prior year period.

◾ Acquired three retail net lease retail properties during the third quarter of 2023 for total acquisition volume of $19.4 million, reflecting a weighted average going-in cash cap rate of 9.0%.

◾ Originated a $7.8 million first mortgage construction loan at a fixed interest rate of 8.5%, secured by a 33-acre land development project anchored by Wawa in a submarket of Indianapolis, Indiana.

◾ Sold eight retail net lease properties during the third quarter of 2023 for total disposition volume of $20.6 million at a weighted average exit cash cap rate of 6.3%, generating total gains of $2.6 million.

◾ Increased investment grade-rated tenant exposure to 64% as of September 30, 2023, up from 49% as of September 30, 2022.

◾ Repurchased 280,332 shares of the Company’s common stock during the third quarter of 2023 for a total cost of $4.7 million, or an average price of $16.78 per share.

◾ Paid a cash dividend for the third quarter of 2023 of $0.275 per share, representing an annualized yield of 6.7% based on the closing price of the Company’s common stock on October 18, 2023.

◾ Book value as of September 30, 2023 was $19.12 per share.

CEO Comments

"Our third quarter results were driven by our differentiated asset recycling program and continued focus on identifying value in a transactions market that we believe has been slow to reprice in the rising interest rate environment," said John P. Albright, President and Chief Executive Officer of Alpine Income Property Trust. "Our transaction activities during the quarter were well-diversified, as we took advantage of strong buyer demand for our non-investment grade assets, acquired properties supported by attractive real estate fundamentals at above market cap rates, and invested in

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our existing portfolio with the repurchase of nearly $5 million of our common equity. As we look forward to the balance of the year, we’ve reduced our guidance in consideration of more conservative expectations regarding the timing of investment activity, a tenant bankruptcy, and increased borrowing costs. Given that we have significantly upgraded our portfolio over the past few years, we believe we are well-suited for what is becoming a more challenging environment.”

Quarterly Operating Results Highlights

The table below provides a summary of the Company’s operating results for the quarter ended September 30, 2023 (in thousands, except per share data):

	Three Months Ended September 30, 2023		Three Months Ended September 30, 2022		Variance to Comparable Period in the Prior Year
Total Revenues	$	11,559	$	11,520	$	39	0.3%
Net Income (Loss)	$	(939)	$	11,170	$	(12,109)	(108.4%)
Net Income (Loss) Attributable to PINE	$	(837)	$	9,770	$	(10,607)	(108.6%)
Net Income (Loss) per Diluted Share Attributable to PINE	$	(0.05)	$	0.72	$	(0.77)	(107.4%)
FFO (1)	$	5,867	$	5,425	$	442	8.1%
FFO per Diluted Share (1)	$	0.37	$	0.40	$	(0.03)	(7.5%)
AFFO (1)	$	5,932	$	5,676	$	256	4.5%
AFFO per Diluted Share (1)	$	0.38	$	0.42	$	(0.04)	(9.5%)
Dividends Declared and Paid, per Share	$	0.275	$	0.275	$	0.000	0.0%

(1) See the “Non-GAAP Financial Measures” section and tables at the end of this press release for a discussion and reconciliation of Net Income to non-GAAP financial measures, including FFO, FFO per diluted share, AFFO, and AFFO per diluted share.

Year-to-Date Operating Results Highlights

The table below provides a summary of the Company’s operating results for the nine months ended September 30, 2023 (in thousands, except per share data):

	Nine Months Ended September 30, 2023		Nine Months Ended September 30, 2022		Variance to Comparable Period in the Prior Year
Total Revenues	$	34,063	$	33,599	$	464	1.4%
Net Income	$	2,896	$	28,430	$	(25,534)	(89.8%)
Net Income Attributable to PINE	$	2,582	$	24,858	$	(22,276)	(89.6%)
Net Income per Diluted Share Attributable to PINE	$	0.16	$	1.84	$	(1.68)	(91.1%)
FFO (1)	$	17,264	$	18,414	$	(1,150)	(6.2%)
FFO per Diluted Share (1)	$	1.10	$	1.36	$	(0.26)	(19.1%)

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AFFO (1)	$	17,410	$	18,473	$	(1,063)	(5.8%)
AFFO per Diluted Share (1)	$	1.11	$	1.37	$	(0.26)	(19.0%)
Dividends Declared and Paid, per Share	$	0.825	$	0.815	$	0.010	1.2%

⁽¹⁾ See the “Non-GAAP Financial Measures” section and tables at the end of this press release for a discussion and reconciliation of Net Income to non-GAAP financial measures, including FFO, FFO per diluted share, AFFO, and AFFO per diluted share.

Investments

During the three months ended September 30, 2023, the Company acquired three high-quality net lease properties for total acquisition volume of $19.4 million, reflecting a weighted average going-in cash cap rate of 9.0%. As of the acquisition date, the properties had a weighted average remaining lease term of 12.6 years, were located in three states, and were leased to tenants operating in three retail sectors, including the dollar stores, health & fitness, and general merchandise sectors.

During the nine months ended September 30, 2023, the Company acquired 12 high-quality net lease properties for total acquisition volume of $79.9 million, reflecting a weighted average going-in cash cap rate of 7.4%. As of the acquisition date, the properties had a weighted average remaining lease term of 8.7 years, were located in seven states, and were leased to tenants operating in ten retail sectors, including the off-price retail, general merchandise, quick service restaurant, casual dining, consumer electronics, sporting goods, home improvement, dollar stores, and health & fitness sectors. Approximately 61% of annualized base rents acquired are generated from a tenant or the parent of a tenant with an investment grade credit rating.

During the three and nine months ended September 30, 2023, the Company entered into a first mortgage construction loan agreement to provide $7.8 million of funding towards the development of a 33-acre land development project anchored by Wawa in a submarket of Indianapolis, Indiana. The two-year first mortgage is interest-only through maturity, includes an origination fee, and bears a fixed interest rate of 8.5%.

Dispositions

During the three months ended September 30, 2023, the Company sold eight properties for total disposition volume of $20.6 million at a weighted average exit cash cap rate of 6.3%, generating total gains of $2.6 million.

During the nine months ended September 30, 2023, the Company sold 22 properties for total disposition volume of $99.6 million at a weighted average exit cash cap rate of 6.2%, generating total gains of $7.8 million.

Property Portfolio

The Company’s portfolio consisted of the following as of September 30, 2023:

Number of Properties	138
Square Feet	3.9 million
Annualized Base Rent	$39.2 million
Weighted Average Remaining Lease Term	7.1 years
States where Properties are Located	35
Occupancy	99.1%

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% of Annualized Base Rent Attributable to Investment Grade Rated Tenants (1)(2)	64%
% of Annualized Base Rent Attributable to Credit Rated Tenants (1)(3)	87%

Any differences are a result of rounding.

⁽¹⁾ Annualized Base Rent (“ABR”) represents the annualized in-place straight-line base rent required by the tenant’s lease. ABR is a non-GAAP financial measure.  We believe this non-GAAP financial measure is useful to investors because it is a widely accepted industry measure used by analysts and investors to compare the real estate portfolios and operating performance of REITs.  

⁽²⁾ The Company defines an Investment Grade Rated tenant as a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners of Baa3, BBB-, or NAIC-2 or higher.

⁽³⁾ The Company defines a Credit Rated Tenant as a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners.

The Company’s portfolio included the following top tenants that represent 2.0% or greater of the Company's total annualized base rent as of September 30, 2023:

Tenant	Credit Rating (1)	% of Annualized Base Rent
Walgreens	BBB	12%
Lowe’s	BBB+	9%
Dick’s Sporting Goods	BBB	9%
Dollar Tree/Family Dollar	BBB	8%
Dollar General	BBB	5%
Walmart	AA	5%
Best Buy	BBB+	4%
At Home	CCC	4%
Hobby Lobby	N/A	3%
Home Depot	A	3%
LA Fitness	B-	2%
Kohl’s	BB	2%
Burlington	BB+	2%
Other		32%
Total		100%

Any differences are a result of rounding.

⁽¹⁾ Credit rating is from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners, as applicable, as of September 30, 2023. The Company defines an Investment Grade Rated tenant as a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners of Baa3, BBB-, or NAIC-2 or higher.

The Company’s portfolio consisted of the following industries as of September 30, 2023:

Industry	% of Annualized Base Rent
Dollar Stores	13%
Pharmacy	13%
Home Improvement	13%
Sporting Goods	12%
Home Furnishings	8%
General Merchandise	6%
Consumer Electronics	6%
Grocery	5%
Entertainment	5%

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Off-Price Retail		4%
Health & Fitness		4%
Specialty Retail		3%
Automotive Parts		2%
Convenience Stores		2%
Farm & Rural Supply		1%
Office Supplies		1%
Quick Service Restaurant		1%
Casual Dining		< 1%
Pet Supplies		< 1%
Other (1)		< 1%
Total	23 Industries	100%

Any differences are a result of rounding.

⁽¹⁾ Includes four industries collectively representing less than 1% of the Company’s ABR as of September 30, 2023.

The Company’s portfolio included properties in the following states as of September 30, 2023:

State	% of Annualized Base Rent
New Jersey	12%
Texas	9%
New York	9%
Michigan	8%
Ohio	7%
Georgia	5%
Florida	5%
Illinois	4%
Oklahoma	4%
West Virginia	4%
Alabama	3%
Minnesota	3%
Kansas	3%
Arizona	2%
Wisconsin	2%
Louisiana	2%
Missouri	2%
Massachusetts	2%
Maryland	2%
Nevada	2%
South Carolina	2%
Pennsylvania	2%
Kentucky	1%
Connecticut	1%
Indiana	1%
New Mexico	1%
Nebraska	<1%

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Maine		<1%
Arkansas		<1%
North Carolina		< 1%
Washington		< 1%
South Dakota		< 1%
California		< 1%
Virginia		< 1%
Mississippi		< 1%
Total	35 States	100%

Any differences are a result of rounding.

Capital Markets and Balance Sheet

During the quarter ended September 30, 2023, the Company completed the following notable capital markets activity:

◾ Repurchased 280,332 shares of the Company’s common stock on the open market under the previously authorized $15.0 million buyback program for a total cost of $4.7 million, or an average price of $16.78 per share.

The following table provides a summary of the Company’s long-term debt as of September 30, 2023:

Component of Long-Term Debt	Principal		Interest Rate	Maturity Date
2026 Term Loan (1)	$	100.0 million	SOFR + 10 bps + [1.35% - 1.95%]	May 2026
2027 Term Loan (2)	$	100.0 million	SOFR + 10 bps + [1.25% - 1.90%]	January 2027
Revolving Credit Facility (3)	$	50.0 million	SOFR + 10 bps + [1.25% - 2.20%]	January 2027
Total Debt/Weighted Average Rate	$	250.0 million	3.36%

⁽¹⁾ As of September 30, 2023, the Company has utilized interest rate swaps to fix SOFR and achieve a weighted average fixed interest rate of 2.05% plus the SOFR adjustment of 0.10% and the applicable spread for the $100 million 2026 Term Loan balance.

⁽²⁾ As of September 30, 2023, the Company has utilized interest rate swaps to fix SOFR and achieve a weighted average fixed interest rate of 1.18% plus the SOFR adjustment of 0.10% and the applicable spread for the $100 million 2027 Term Loan balance.

⁽³⁾ As of September 30, 2023, the Company has utilized interest rate swaps to fix SOFR and achieve a weighted average fixed interest rate of 3.21% plus the SOFR adjustment of 0.10% and the applicable spread for the $50 million balance on the Company’s Revolving Credit Facility.

As of September 30, 2023, the Company held an 89.0% interest in Alpine Income Property OP, LP, the Company’s operating partnership (the “Operating Partnership” or “OP”).  There were 1,703,494 OP Units held by third parties outstanding and 13,769,609 shares of the Company’s common stock outstanding, for total outstanding common stock and OP Units held by third parties of 15,473,103, as of September 30, 2023.

As of September 30, 2023, the Company’s net debt to Pro Forma EBITDA was 6.9 times, and as defined in the Company’s credit agreement, the Company’s fixed charge coverage ratio was 3.4 times. As of September 30, 2023, the Company’s net debt to total enterprise value was 47.9%. The Company calculatestotal enterprise value as the sum of net debt and the market value of the Company's outstanding common shares and OP Units, as if the OP Units have been converted to common shares.

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Dividend

On August 23, 2023, the Company announced a cash dividend for the third quarter of 2023 of $0.275 per share, payable on September 29, 2023 to stockholders of record as of the close of business on September 14, 2023. The third quarter 2023 cash dividend represents payout ratios of 74.3% and 72.4% of the Company’s third quarter 2023 FFO per diluted share and AFFO per diluted share, respectively.

2023 Outlook

The Company has revised its outlook for 2023 to take into account the Company’s year-to-date performance and revised expectations regarding the Company’s investment activities, forecasted capital markets transactions, and other significant assumptions.  

The Company’s revised outlook for 2023 is as follows:

	Revised Outlook Range for 2023				Change from Prior Outlook
	Low		High	Low			High
Acquisitions	$100 million	to	$125 million	-		to	-
Dispositions	$100 million	to	$125 million	-		to	-
FFO per Diluted Share	$1.45	to	$1.47	($0.05)		to	($0.06)
AFFO per Diluted Share	$1.46	to	$1.48	($0.06)		to	($0.07)
Weighted Average Diluted Shares Outstanding	15.6 million	to	15.6 million	0.1 million		to	(0.4) million

Third Quarter 2023 Earnings Conference Call & Webcast

The Company will host a conference call to present its financial and operating results for the quarter ended September 30, 2023, on Friday, October 20, 2023, at 9:00 AM ET.

A live webcast of the call will be available on the Investor Relations page of the Company’s website at www.alpinereit.com or at the link provided in the event details below. To access the call by phone, please go to the link provided in the event information below and you will be provided with dial-in details.

Webcast:https://edge.media-server.com/mmc/p/fg68mtir

Dial-In:https://register.vevent.com/register/BI7fdbafb88c2e4305bc44b67274dc0cca 

We encourage participants to dial into the conference call at least fifteen minutes ahead of the scheduled start time. A replay of the earnings call will be archived and available online through the Investor Relations section of the Company’s website at www.alpinereit.com.

About Alpine Income Property Trust, Inc.

Alpine Income Property Trust, Inc. (NYSE: PINE) is a publicly traded real estate investment trust that seeks to deliver attractive risk-adjusted returns and dependable cash dividends by investing in, owning and operating a portfolio of single tenant net leased commercial income properties that are predominately leased to high-quality publicly traded and credit-rated tenants.

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We encourage you to review our most recent investor presentation which is available on our website at http://www.alpinereit.com.

Safe Harbor

This press release may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “might,” “will,” “likely,” “anticipates,” “intends,” “plans,” “seeks,” “believes,” “estimates,” “expects,” “continues,” “projects” and similar references to future periods, or by the inclusion of forecasts or projections. Forward-looking statements are based on the Company’s current expectations and assumptions regarding capital market conditions, the Company’s business, the economy and other future conditions. Because forward-looking statements relate to the future, by their nature, they are subject to inherent uncertainties, risks and changes in circumstances that are difficult to predict. As a result, the Company’s actual results may differ materially from those contemplated by the forward-looking statements. Important factors that could cause actual results to differ materially from those in the forward-looking statements include general business and economic conditions, continued volatility and uncertainty in the credit markets and broader financial markets, risks inherent in the real estate business, including tenant defaults, potential liability relating to environmental matters, credit risk associated with the Company investing in commercial loans and investments, illiquidity of real estate investments and potential damages from natural disasters, the impact of epidemics or pandemics (such as the COVID-19 Pandemic and its variants) on the Company’s business and the business of its tenants and the impact of such epidemics or pandemics on the U.S. economy and market conditions generally, other factors affecting the Company’s business or the business of its tenants that are beyond the control of the Company or its tenants, and the factors set forth under “Risk Factors” in the Company’s Annual Report on Form 10-K for the year ended December 31, 2022, the Company’s Quarterly Report on Form 10-Q for the quarter ended September 30, 2023 and other risks and uncertainties discussed from time to time in the Company’s filings with the U.S. Securities and Exchange Commission. Any forward-looking statement made in this press release speaks only as of the date on which it is made. The Company undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise.

Non-GAAP Financial Measures

Our reported results are presented in accordance with accounting principles generally accepted in the United States of America (“GAAP”). We also disclose Funds From Operations (“FFO”) Adjusted Funds From Operations (“AFFO”), and Pro Forma Earnings Before Interest, Taxes, Depreciation and Amortization (“Pro Forma EBITDA”), all of which are non-GAAP financial measures. We believe these non-GAAP financial measures are useful to investors because they are widely accepted industry measures used by analysts and investors to compare the operating performance of REITs.

FFO, AFFO, and Pro Forma EBITDA do not represent cash generated from operating activities and are not necessarily indicative of cash available to fund cash requirements; accordingly, they should not be considered alternatives to net income as a performance measure or cash flows from operations as reported on our statement of cash flows as a liquidity measure and should be considered in addition to, and not in lieu of, GAAP financial measures.

We compute FFO in accordance with the definition adopted by the Board of Governors of the National Association of Real Estate Investment Trusts, or NAREIT. NAREIT defines FFO as GAAP net income or loss adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries.

To derive AFFO, we modify the NAREIT computation of FFO to include other adjustments to GAAP net income related to non-cash revenues and expenses such as loss on extinguishment of debt, amortization of above- and below-market lease related intangibles, straight-line rental revenue, amortization of deferred financing costs, non-cash

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compensation, and other non-cash income or expense. Such items may cause short-term fluctuations in net income but have no impact on operating cash flows or long-term operating performance. We use AFFO as one measure of our performance when we formulate corporate goals.

To derive Pro Forma EBITDA, GAAP net income or loss is adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries, non-cash revenues and expenses such as straight-line rental revenue, amortization of deferred financing costs, loss on extinguishment of debt, above- and below-market lease related intangibles, non-cash compensation, and other non-cash income or expense. Cash interest expense is also excluded from Pro Forma EBITDA, and GAAP net income or loss is adjusted for the annualized impact of acquisitions, dispositions and other similar activities.

FFO is used by management, investors and analysts to facilitate meaningful comparisons of operating performance between periods and among our peers primarily because it excludes the effect of real estate depreciation and amortization and net gains or losses on sales, which are based on historical costs and implicitly assume that the value of real estate diminishes predictably over time, rather than fluctuating based on existing market conditions. We believe that AFFO is an additional useful supplemental measure for investors to consider because it will help them to better assess our operating performance without the distortions created by other non-cash revenues or expenses. We also believe that Pro Forma EBITDA is an additional useful supplemental measure for investors to consider as it allows for a better assessment of our operating performance without the distortions created by other non-cash revenues, expenses or certain effects of the Company’s capital structure on our operating performance. FFO, AFFO, and Pro Forma EBITDA may not be comparable to similarly titled measures employed by other companies.

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Alpine Income Property Trust, Inc.

Consolidated Balance Sheets

(In thousands, except share and per share data) 

	As of
	(Unaudited) September 30, 2023		December 31, 2022
ASSETS
Real Estate:
Land, at Cost	$	150,425	$	176,857
Building and Improvements, at Cost		332,654		322,510
Total Real Estate, at Cost		483,079		499,367
Less, Accumulated Depreciation		(31,517)		(22,313)
Real Estate—Net		451,562		477,054
Assets Held for Sale		4,410		—
Commercial Loans and Investments		6,874		—
Cash and Cash Equivalents		6,265		9,018
Restricted Cash		11,166		4,026
Intangible Lease Assets—Net		51,624		60,432
Straight-Line Rent Adjustment		1,483		1,668
Other Assets		24,293		21,233
Total Assets	$	557,677	$	573,431
LIABILITIES AND EQUITY
Liabilities:
Accounts Payable, Accrued Expenses, and Other Liabilities	$	5,625	$	4,411
Prepaid Rent and Deferred Revenue		1,884		1,479
Intangible Lease Liabilities—Net		5,184		5,050
Long-Term Debt		249,099		267,116
Total Liabilities		261,792		278,056
Commitments and Contingencies
Equity:
Preferred Stock, $0.01 par value per share, 100 million shares authorized, no shares issued and outstanding as of September 30, 2023 and December 31, 2022		—		—
Common Stock, $0.01 par value per share, 500 million shares authorized, 13,769,609 shares issued and outstanding as of September 30, 2023 and 13,394,677 shares issued and outstanding as of December 31, 2022		138		134
Additional Paid-in Capital		244,300		236,841
Retained Earnings		1,075		10,042
Accumulated Other Comprehensive Income		17,706		14,601
Stockholders' Equity		263,219		261,618
Noncontrolling Interest		32,666		33,757
Total Equity		295,885		295,375
Total Liabilities and Equity	$	557,677	$	573,431

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Alpine Income Property Trust, Inc.

Consolidated Statements of Operations

(Unaudited)

(In thousands, except share, per share and dividend data) 

	Three Months Ended					Nine Months Ended
	September 30, 2023			September 30, 2022		September 30, 2023		September 30, 2022
Revenues:
Lease Income	$	11,447		$	11,520	$	33,951	$	33,599
Interest Income from Commercial Loans and Investments		112			—		112		—
Total Revenues		11,559			11,520		34,063		33,599
Operating Expenses:
Real Estate Expenses		1,722			1,816		4,731		4,193
General and Administrative Expenses		1,652			1,460		4,823		4,370
Provision for Impairment		2,864			—		2,864		—
Depreciation and Amortization		6,528			5,866		19,286		17,232
Total Operating Expenses		12,766			9,142		31,704		25,795
Gain on Disposition of Assets		2,586			11,611		7,782		27,248
Gain (Loss) on Extinguishment of Debt		—			(284)		23		(284)
Net Income from Operations		1,379			13,705		10,164		34,768
Investment and Other Income		125			9		226		9
Interest Expense		(2,443)			(2,544)		(7,494)		(6,347)
Net Income (Loss)		(939)			11,170		2,896		28,430
Less: Net Income (Loss) Attributable to Noncontrolling Interest		(102)			1,400		314		3,572
Net Income (Loss) Attributable to Alpine Income Property Trust, Inc.	$	(837)		$	9,770	$	2,582	$	24,858
Per Common Share Data:
Net Income (Loss) Attributable to Alpine Income Property Trust, Inc.
Basic	$	(0.06)		$	0.82	$	0.18	$	2.11
Diluted	$	(0.05)		$	0.72	$	0.16	$	1.84
Weighted Average Number of Common Shares:
Basic	13,946,194		11,888,171			14,001,774		11,799,151
Diluted (1)	15,649,688			13,591,665		15,705,268		13,502,645
Dividends Declared and Paid	$	0.275		$	0.275	$	0.825	$	0.815

⁽¹⁾ Includes the weighted average impact of 1,703,494 shares underlying OP units including (i) 1,223,854 shares underlying OP Units issued to CTO Realty Growth, Inc. and (ii) 479,640 shares underlying OP Units issued to an unrelated third party.

Page 11

Alpine Income Property Trust, Inc.

Non-GAAP Financial Measures

Funds From Operations and Adjusted Funds From Operations

(Unaudited)

(In thousands, except per share data) 

	Three Months Ended					Nine Months Ended
	September 30, 2023			September 30, 2022		September 30, 2023		September 30, 2022
Net Income (Loss)		$	(939)	$	11,170	$	2,896	$	28,430
Depreciation and Amortization			6,528		5,866		19,286		17,232
Provision for Impairment			2,864		—		2,864		—
Gain on Disposition of Assets			(2,586)		(11,611)		(7,782)		(27,248)
Funds from Operations		$	5,867	$	5,425	$	17,264	$	18,414
Adjustments:
Straight-Line Rent Adjustment			(112)		(209)		(386)		(737)
Loss (Gain) on Extinguishment of Debt			—		284		(23)		284
COVID-19 Rent Repayments			—		—		—		45
Non-Cash Compensation			79		79		238		236
Amortization of Deferred Financing Costs to Interest Expense			179		150		530		407
Amortization of Intangible Assets and Liabilities to Lease Income			(110)		(78)		(299)		(248)
Other Non-Cash Expense			29		25		86		72
Adjusted Funds from Operations		$	5,932	$	5,676	$	17,410	$	18,473
FFO per Diluted Share		$	0.37	$	0.40	$	1.10	$	1.36
AFFO per Diluted Share		$	0.38	$	0.42	$	1.11	$	1.37

Page 12

Alpine Income Property Trust, Inc.

Non-GAAP Financial Measures

Reconciliation of Net Debt to Pro Forma EBITDA

(Unaudited)

(In thousands) 

	Three Months Ended
	September 30, 2023
Net Income (Loss)	$	(939)
Adjustments:
Depreciation and Amortization		6,528
Provision for Impairment		2,864
Gains on Disposition of Assets		(2,586)
Straight-Line Rent Adjustment		(112)
Non-Cash Compensation		79
Amortization of Deferred Financing Costs to Interest Expense		179
Amortization of Intangible Assets and Liabilities to Lease Income		(110)
Other Non-Cash Expense		29
Interest Expense, Net of Deferred Financing Costs Amortization		2,264
EBITDA	$	8,196
Annualized EBITDA	$	32,784
Pro Forma Annualized Impact of Current Quarter Acquisitions and Dispositions, Net (1)		949
Pro Forma EBITDA	$	33,733
Total Long-Term Debt		249,099
Financing Costs, Net of Accumulated Amortization		901
Cash and Cash Equivalents		(6,265)
Restricted Cash		(11,166)
Net Debt	$	232,569
Net Debt to Pro Forma EBITDA		6.9x

⁽¹⁾ Reflects the pro forma annualized impact on Annualized EBITDA of the Company’s investments and disposition activity during the three months ended September 30, 2023.

Page 13

EX-99.2

Exhibit 99.2

October 2023 Investor Presentation

2 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com National, Investment Grade Tenant-Focused Net Lease Portfolio Ticker Symbol (NYSE) PINE Equity Market Capitalization $253M Total Enterprise Value (TEV) $486M TEV Per Square Foot $125 Implied Cap Rate 7.9% Annualized Dividend Yield 6.7% Common Shares & OP Units Outstanding2 15.5M Number of Net Lease Properties 138 Number of States with a Property 35 Total Portfolio Square Feet 3.9M Current Occupancy 99.1% Annualized Base Rent (ABR) $39.2M % of ABR from Investment Grade-Rated Tenants1 64% % of ABR from Credit Rated Tenants1 87% As of September 30, 2023, unless otherwise noted. 1. A credit rated, or investment grade rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners (NAIC). 2. As of October 19, 2023; includes 1,703,494 OP Units held by third parties in Alpine Income Property OP, LP, the Company’s operating partnership (the “Operating Partnership” or “OP”).

3 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Alpine’s Value Proposition Meaningful Valuation Upside with In-Place Yield and Long-Term Growth Accretive Asset Recycling Driving Attractive Portfolio Metrics Pure play, 100% retail portfolio growing through accretive asset recycling of predominantly non-investment grade assets at attractive pricing, with reinvestment focused on investment grade-rated tenants and high-quality assets with strong real estate fundamentals. Opportunity to Invest Below Replacement Cost PINE’s total enterprise value (TEV) is $125 per square foot and book value is $19.12 per share, allowing shareholders to invest meaningfully below replacement cost in a portfolio rooted in higher credit quality tenants in major markets throughout the United States. Significant Discount to Peer Group PINE trades at a significant discount compared to its investment grade-focused peers, implying considerable valuation upside. Stable & Attractive Dividend PINE has grown its quarterly dividend by 37.5% since the beginning of 2020 and now provides one of the highest dividend yields of its net lease peer group. As of September 30, 2023, unless otherwise noted. 1. All dividend yields, payout ratios and 2023E FFO multiples are based on the closing stock price on September 29, 2023, using current annualized dividends and 2023E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 10/1/2023 report. 2023E FFO per share for PINE reflects the midpoint of guidance provided on October 19, 2023. 2. Based on 2023 Average Household Income (5-mile) and 2023 Total Population (5-mile) data from Esri. Payout Ratio % 6.7% FCPT PINE O ADC SRC NTST NNN EPRT 2023E FFO Payout Ratio Dividend Yield 13.9x 13.6x 13.5x 12.3x 12.1x 11.3x 11.0x 9.2x ADC FCPT NTST EPRT O PINE NNN SRC 2023E FFO Multiple 1  Total Enterprise Value of $124 per square foot  $100,120 Total Portfolio Weighted Average 5-Mile Average Household Income2  114,475 Total Portfolio Weighted Average 5-Mile Total Population2 1 1 PINE’s top 10 tenants now include investment grade-rated industry leaders such as:

4 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Accretive Asset Recycling 5.8% 5.5% 5.8% 5.5% 6.5% 6.1% 6.2% 6.3% Q3 2020 Q3 2021 Q2 2022 Q3 2022 Q4 2022 Q1 2023 Q2 2023 Q3 2023 Retail Disposition Cap Rates Retail Properties Sold As of September 30, 2023. PINE has demonstrated a consistent ability to sell retail properties at attractive valuations, regardless of the tenant credit quality, to drive accretive acquisitions of predominantly investment grade-rated tenants at an average positive spread of more than 100 basis points between its retail disposition and retail acquisition cap rates.

5 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Opportunity to Invest Below Replacement Cost High-Quality Portfolio with Valuation Upside PINE’s total enterprise value (TEV) is $125 per square foot, allowing shareholders to invest below estimated replacement cost in a portfolio rooted in higher growth, major markets throughout the United States with comparable tenants to the investment grade-focused net lease peers. Better Margin of Safety with Stickier Tenants With an average cash rent per square foot of $10.05, occupancy costs for PINE’s portfolio tenants are meaningfully below market rents given the inflationary pressure on building and land costs, suggesting tenants will be more likely to exercise their renewal options at expiration. Significant Valuation Discount to Peer Group Similar tenant exposures in comparable or better markets, with an underlying real estate valuation per square foot 48% below the peer average. Creating Value Through Capital Recycling PINE has maintained its disposition guidance, implying it will continue to monetize assets at attractive private market valuations, resulting in accretive net investment spreads once disposition proceeds are reinvested. 1. Value is based on Total Enterprise Value for each peer net lease company is from the Stifel Triple-Net REITs Comp Sheets 10/1/2023 report. 2. Portfolio size is based on total square feet and is from available information within each company’s published information available through each company’s website, as of September 30, 2023. Portfolio information for PINE is as of September 30, 2023. FCPT NNN EPRT O ADC NTST SRC PINE $0 $100 $200 $300 $400 $500 0 50 100 150 200 250 300 Value 1 Per Square Foot 2 Portfolio Size (Square Feet) 2 Peer Average $241

6 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Significant Implied Valuation Upside 13.9x 13.6x 13.5x 12.3x 12.1x 11.3x 11.0x 9.2x ADC FCPT NTST EPRT O PINE NNN SRC 2023E FFO Multiple 1 PINE trades at a 2.4x multiple discount to the investment grade-focused peer group average, implying significant valuation upside Investment Grade-Focused Peer Average 13.7x 68% 59% 68% 18% Not Disclosed 40% 64% 19% As of September 30, 2023, unless otherwise noted. 1. All dividend yields, payout ratios and 2023E FFO multiples are based on the closing stock price on September 30, 2023, using current annualized dividends and 2023E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 10/1/2023 report. 2023E FFO per share for PINE reflects the midpoint of guidance provided on October 19, 2023. 2. A credit rated, or investment grade (“IG”) rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners. 3. Percentage of rents associated with investment grade-rated tenants based on published information available through each company’s website as of September 30, 2023. IGRATED Disclosed % of Rents from Investment Grade-Rated Tenants2,3

7 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Relative Outsized In-Place Dividend Yield 1. All dividend yields and payout ratios are based on the closing stock price on September 30, 2023, using current annualized dividends and 2023E FFO per share estimates for the peer net lease companies from the Stifel Triple-Net REITs Comp Sheets 10/1/2023 report. 2023E FFO per share for PINE reflects the midpoint of guidance provided on October 19, 2023. 83% 76% 75% 74% 74% 71% 70% 64% 6.1% 6.7% 6.1% 5.3% 8.0% 5.3% 6.4% 5.2% FCPT PINE O ADC SRC NTST NNN EPRT 2023E FFO Payout Ratio Dividend Yield Peer Average 6.1% PINE’s dividend is strongly supported by a conservative payout ratio and a portfolio built with an intense focus on real estate fundamentals, high-quality tenancy and long-term stability.

8 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Disciplined Investment Strategy National Focus, Emphasizing Attractive Supply/Demand Dynamics National focus, with an emphasis on major metropolitan statistical areas that exhibit attractive population trends, business-friendly policies and strong underlying supply/demand fundamentals Real Estate Fundamentals and Analytics Driven Underwriting Real estate-oriented underwriting utilizing consumer location data analytics, competition indexing, market rent benchmarking and comprehensive risk assessments Industry-Leading Tenants and Well-Performing Operating Sectors Focused on aligning with tenants operating in essential business sectors, displaying stable and resilient operating trends and/or a forward-thinking, omni-channel strategy Relative Asset Value Investing Through Long-Term Relationships Concentrated on relative value-investing through deep broker, developer and tenant relationships and management’s ability to identify high-quality risk-adjusted opportunities in a highly fragmented transaction market

9 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Thoughtful Investment Execution $47 $75 $99 $117 $139 $220 $275 $377 $442 $486 $523 $564 $564 $625 $644 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 Q1 2023 Q2 2023 Q3 2023 IPO 2021 Q4 2019 Cumulative Investment Activity Since IPO 2022 PINE has prudently invested capital into stable tenants with attractive underlying real estate and strong demographics. As of September 30, 2023. $ in millions. 2023

10 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Improving Portfolio Size, Diversity and Quality As of September 30, 2023. 1. A credit rated, or investment grade (“IG”) rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners. 2019 (IPO) Number of Net Lease Properties 20 48 113 148 138 Number of States with a Property 12 18 32 34 35 Total Portfolio Square Feet 0.9M 1.6M 3.3M 3.7M 3.9M Annualized Base Rent (ABR) $13.3M $21.1M $36.9M $40.4M $39.2M Top Tenant as a % of ABR 21% Wells Fargo (S&P: A+) 15% Wells Fargo (S&P: A+) 8% Wells Fargo (S&P: A+) 11% Walgreens (S&P: BBB) 12% Walgreens (S&P: BBB) Top Sector as a % of ABR 21% Financial Services 15% General Merchandise 12% Home Furnishings 13% Sporting Goods 13% Dollar Stores Top State as a % of ABR 26% Florida 21% Florida 18% Texas 17% Texas 12% New Jersey % of ABR from IG Rated Tenants1 36% 46% 45% 54% 64% % of ABR from Credit Rated Tenants1 89% 83% 74% 79% 87% % of ABR from Office Properties 43% 27% 8% - % - % 2020 2021 2022 2023

11 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Investment Grade-Focused Portfolio Credit Rating1 BBB 12% BBB+ 9% BBB 9% BBB 8% BBB 5% AA 5% BBB+ 4% CCC 4% N/A 3% A 3% 38% 100% ABR % Other 5% 1% 4% 11% 9% 12% 9% 49% Lease Rollover Schedule % of ABR Expiring 7.1 Years of Weighted Average Lease Term Remaining As of September 30, 2023. 1. A credit rated, or investment grade rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners (NAIC).

12 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com High-Quality Top Tenant Base Disclosed % of Rents from Investment Grade-Rated Tenants1,2 RATED IG 68% 68% 59% 19% 18% As of September 30, 2023, unless otherwise noted. 1. A credit rated, or investment grade (“IG”) rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners. 2. Top ten tenants and percentage of rents associated with investment grade-rated tenants based on published information available through each company’s website as of September 30, 2023. Not Disclosed 64% 40%

13 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Excellent Tenant Credit and Operational Transparency Investment Grade 64% Not Rated 13% Non-Investment Grade 23% Dollar Stores 13% Pharmacy 13% Home Improvement 13% Sporting Goods 12% Home Furnishings 8% General Merchandise 6% Consumer Electronics 6% Grocery 5% Entertainment 5% Off-Price Retail 4% Other 15% 100% ABR % As of September 30, 2023. 1. A credit rated, or investment grade (“IG”) rated tenant (rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners. ▪ 93% of ABR comes from tenants or the parent of a tenant that are credit rated1 or publicly traded, suggesting relatively better tenant financial and operational transparency Sector

14 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Major Market, Demographic-Driven Net Lease Portfolio ▪ Geographically diversified portfolio focused on major markets and areas benefitting from demographic shifts and attractive supply/demand dynamics ▪ 51% of ABR comes from metropolitan statistical areas1 with more than one million people % of Annualized Base Rent By State 3% - 7% > 7% 2% - 3% < 2% As of September 30, 2023. 1. MSA, or metropolitan statistical area, is the formal definition of a region that consists of a city and surrounding communities that are linked by social and economic factors, as established by the U.S. Office of Management and Budget. The names of the MSA have been shortened for ease of reference. 2. Based on 2023 Average Household Income (5-mile) and 2023 Total Population (5-mile) data from Esri. Total Portfolio Weighted Average 5-Mile Average Household Income $100,120 2 Total Portfolio Weighted Average 5-Mile Total Population 114,475 2 ▪ 42% of portfolio ABR comes from the top 10 MSAs1 , with nearly 50% of ABR from the top 10 MSA’s1 comes from the in-demand markets of Houston, Atlanta, Tampa, Philadelphia and New York ▪ Properties in the top 10 MSAs have a weighted average 5-mile average household income of $114,9002 ▪ Properties in the top 10 MSAs have a weighted average 5-mile total population of 141,950 people2

15 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Consistent Dividend Growth Stable, Well-Covered Dividend ▪ Current midpoint of 2023 guidance1 implies a 75% 2023E FFO per share dividend payout ratio ▪ 37.5% increase in the quarterly cash dividend since the beginning of 2020 Annualized Per Share Cash Dividend $1.10 Annualized Per Share Cash Dividend Yield 6.7% As of September 30, 2023, unless otherwise noted. 1. 2023E FFO per share for PINE is the midpoint of guidance, as provided on October 19, 2023. $0.060 $0.200 $0.200 $0.200 $0.220 $0.240 $0.250 $0.255 $0.270 $0.270 $0.270 $0.275 $0.275 $0.275 $0.275 $0.275 Q4 2019 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 Q1 2023 Q2 2023 Q3 2023 IPO Q4 2019 Dividend Per Share Paid 2020 2021 2022 2023

16 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Research Coverage Near Unanimous Buy or Outperform rated by Independent Analysts Baird Wes Golladay Outperform $20.00 B. Riley John Massocca Buy $20.00 BTIG Mike Gorman Buy $23.00 Colliers Barry Oxford Buy $20.00 Janney Rob Stevenson Buy $19.00 Jones Matthew Erdner Buy $22.00 Raymond James RJ Milligan Outperform $19.00 Stifel Simon Yarmak Buy $20.00 Truist Anthony Hau Hold $17.00 Average $20.00 Institution Covering Analyst Rating Price Target As of October 16, 2023.

17 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Financial Strength PINE has a demonstrated access to capital, is focused on maintaining reasonable leverage, and has completely fixed its attractive cost of debt through 2026. Equity Market Capitalization1 $253M Net Debt Outstanding1,2 $233M Total Enterprise Value (TEV)1 $486M Well-Capitalized Balance Sheet Q3 2023 48% Q3 2023 6.9x Q4 2022 47% Q4 2022 7.1x Q4 2021 50% Q4 2021 8.1x No Near-Term Capital Markets Exposure Improved Leverage Profile $50 $100 $100 2023 2024 2025 2026 2027 2028 2029 2030 Revolving Credit Facility Unsecured Term Loans Well-Staggered Debt Maturity Schedule Net Debt to TEV3 Net Debt to Pro Forma EBITDA4 Debt Outstanding 1 5 ▪ PINE has no debt maturities until May 2026 ▪ No current floating interest rate exposure ▪ More than $217 million1 of potential liquidity via cash, restricted cash and undrawn revolving credit facility commitments As of September 30, 2023, unless otherwise noted. $ in millions; any differences a result of rounding. 1. As of September 30, 2023. 2. Net Debt Outstanding is the Company’s outstanding debt, minus the Company’s cash, cash equivalents and restricted cash. 3. Net Debt to TEV (Total Enterprise Value) is the Company’s outstanding debt, minus the Company’s cash, cash equivalents and restricted cash, as a percentage of the Company’s enterprise value. 4. See the “Non-GAAP Financial Information” section and tables at the end of this presentation for a discussion and reconciliation of Net Income to non-GAAP financial measures. 5. Reflects $50.0 million outstanding under the Company’s $250 million senior unsecured revolving credit facility; the Company’s senior unsecured revolving credit facility matures in January 2027 and includes a one-year extension option, subject to satisfaction of certain conditions; the maturity date reflected assumes the Company exercises the one-year extension option.

18 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com 2023 Guidance Range Acquisitions $100 million - $125 million $100 million - $125 million — - — Dispositions $100 million - $125 million $100 million - $125 million — - — FFO Per Diluted Share $1.50 - $1.53 $1.45 - $1.47 ($0.05) - ($0.06) AFFO Per Diluted Share $1.52 - $1.55 $1.46 - $1.48 ($0.06) - ($0.07) Weighted Average Diluted Shares Outstanding 15.5 million - 16.0 million 15.6 million - 15.6 million 0.1 million - (0.4) million Low High The Company’s 2023 revised guidance takes into account the Company’s year-to-date performance and revised expectations regarding the Company’s investment activities, forecasted capital markets transactions, and other significant assumptions. 2023 revised guidance was provided in the Company’s Third Quarter 2023 Operating Results press release filed on October 19, 2023. Low High Low High Previous Guidance Revised Guidance Increase (Decrease)

19 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Corporate Responsibility Alpine Income Property Trust, through its external manager, is committed to sustainability, strong corporate governance, and meaningful corporate social responsibility programs. Committed Focus Committed to maintaining an environmentally conscious culture, the utilization of environmentally friendly & renewable products, and the promotion of sustainable business practices Tenant Alignment Alignment with environmentally aware tenants who have strong sustainability programs and initiatives embedded into their corporate culture and business practices Social Responsibility Environmental Responsibility Corporate Governance ▪ Independent Chairman of the Board and 5 of 6 Directors classified as independent ▪ Annual election of all Directors ▪ Annual Board of Director evaluations ▪ Stock ownership requirements for all Directors ▪ Prohibition against hedging and pledging Alpine Income Property Trust stock ▪ Robust policies and procedures for approval of related party transactions ▪ Opted out of business combination and control share acquisition statutes in the Maryland General Corporation Law ▪ All team members adhere to a comprehensive Code of Business Conduct and Ethics policy Inclusive and Supportive Company Culture Dedicated to an inclusive and supportive office environment filled with diverse backgrounds and perspectives, with a demonstrated commitment to financial, mental and physical wellness Notable Community Outreach Numerous and diverse community outreach programs, supporting environmental, artistic, civil and social organizations in the community

20 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com External Management Alignment As of October 19, 2023. Aligned Ownership CTO currently owns an approximate 15% interest in PINE, meaningfully aligning its interests with PINE shareholders Independent Board of Directors PINE has its own independent Board of Directors and realizes significant economies of scale from the 32-member CTO team without the corresponding G&A expense Shadow Pipeline for External Growth PINE has a potential shadow pipeline within the CTO portfolio as a result of its right of first refusal on all CTO single tenant net lease asset sales Internalization on the Horizon Internalization of management for PINE is anticipated in the future when the Company approaches or exceeds critical mass Opportunities for Collaboration PINE reviews transaction opportunities resulting from CTO’s acquisition efforts that it otherwise would not see in the market through normal single tenant acquisition efforts and relationships Benefits and Alignment of External Management Notable Management Agreement Terms ▪ Five-year initial term (initial expiration November 2024), with one-year extension options thereafter ▪ Quarterly management fee of 0.375%, calculated on equity, net of share buybacks and issuance costs ▪ Terminable with payment of a one-time fee of 3x the annualized average management fee for the preceding 24-months Alpine Income Property Trust is externally managed by CTO Realty Growth (NYSE: CTO) under an agreement that, combined with CTO’s ownership in PINE, provides economies of scale, significant shareholder alignment and a flexible/collapsible structure.

21 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Board of Directors Our Board has a well-balanced mix of perspectives and experiences and maintains relevant policies to ensure shareholder alignment, risk management, corporate oversight and the highest ethical standards. Andrew C. Richardson Chairman of the Board, Independent Director Currently Chief Executive Officer of RMC Living. Former Chief Operating Officer of Waypoint Real Estate Investments, Chief Financial Officer and President of Land and Development of iStar, Inc. (NYSE: STAR), Chief Financial Officer of The Howard Hughes Corporation (NYSE: HHC) and Chief Financial Officer of NorthStar Realty Finance Corp. Chairman of the Board and Chairman of the Audit Committee. Mark O. Decker Jr. Independent Director Currently Managing Director of Proterra Investment Partners. Former President, Chief Executive Officer and Chief Investment Officer, and Director of CenterSpace and Former Managing Director and U.S. Group Head of Real Estate Investment and Corporate Banking at BMO Capital Markets. Member of the Audit and Governance Committees. Jeffrey S. Yarckin Independent Director Currently Founder, President, and COO of TriGate Capital, LLC. Former Co-President and Chief Executive Officer of ORIX Capital Markets, LLC. Former Founding Partner of the Lone Star Funds. Chairman of the Compensation Committee and a member of the Governance Committee. John P. Albright President & CEO Currently President & Chief Executive Officer of Alpine Income Property Trust (NYSE: PINE) and CTO Realty Growth (NYSE: CTO). Former Co-Head and Managing Director of Archon Capital, a Goldman Sachs Company; Executive Director of Merchant Banking – Investment Management at Morgan Stanley; and Managing Director of Crescent Real Estate (NYSE: CEI). Rachel Elias Wein Independent Director Currently Founder and Chief Executive Officer of WeinPlus. Former development executive with The Sembler Company and senior associate with Ernst & Young’s Real Estate Advisory practice. Member of the Audit Committee and the Compensation Committee. M. Carson Good Independent Director Currently President of Good Capital Group. Former Managing Director and Florida Broker of Record for Jones Lang LaSalle (NYSE: JLL) and current Chairman of the Board of the Greater Orlando Airport Authority (GOAA). Chairman of the Governance Committee and a member of the Compensation Committee

22 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Key Takeaways Significant Discount to Peer Group Meaningful upside opportunity as PINE has the lowest 2023E FFO multiples of its investment grade-focused net lease peer group. Stable & Growing Dividend PINE has grown its quarterly dividend by 37.5% since the beginning of 2020 and currently has a very efficient 2023E FFO1 implied payout ratio of approximately 75%. Small Asset Base is an Opportunity for Outsized Growth Small asset denominator means management can drive outsized growth relative to its net lease peers. Disciplined Investment Strategy Real estate and credit-focused underwriting, targeting investments that exhibit strong demographic trends, leased to high-quality, industry-leading tenants. High-Quality, Transparent and Growing Portfolio 100% retail portfolio rooted in publicly-traded/credit-rated tenants and larger markets means there is a high-quality, stable asset base and an opportunity to add a diverse array of new tenants, markets and sectors. Financial Stability Balance sheet with ample liquidity and no near-term debt maturities provides financial stability and flexibility. Aligned Sponsorship & Management Externally managed by CTO Realty Growth (NYSE: CTO), a publicly traded REIT that owns 15% of PINE and is committed to internalization of management once critical mass is attained. As of September 30, 2023, unless otherwise noted. 1. 2023E FFO per share for PINE is the midpoint of guidance, as provided on October 19, 2023.

23 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Disclaimer This presentation may contain “forward-looking statements.” Forward-looking statements include statements that may be identified by words such as “could,” “may,” “might,” “will,” “likely,” “anticipates,” “intends,” “plans,” “seeks,” “believes,” “estimates,” “expects,” “continues,” “projects” and similar references to future periods, or by the inclusion of forecasts or projections. Forward-looking statements are based on the Company’s current expectations and assumptions regarding capital market conditions, the Company’s business, the economy and other future conditions. Because forward-looking statements relate to the future, by their nature, they are subject to inherent uncertainties, risks and changes in circumstances that are difficult to predict. As a result, the Company’s actual results may differ materially from those contemplated by the forward-looking statements. Important factors that could cause actual results to differ materially from those in the forward-looking statements include general business and economic conditions, continued volatility and uncertainty in the credit markets and broader financial markets, risks inherent in the real estate business, including tenant defaults, potential liability relating to environmental matters, credit risk associated with the Company investing in commercial loans and investments, illiquidity of real estate investments and potential damages from natural disasters, the impact of the COVID-19 Pandemic and its variants on the Company’s business and the business of its tenants and the impact on the U.S. economy and market conditions generally, other factors affecting the Company’s business or the business of its tenants that are beyond the control of the Company or its tenants, and the factors set forth under “Risk Factors” in the Company’s Annual Report on Form 10-K for the year ended December 31, 2022, the Company’s Quarterly Report on Form 10-Q for the quarter ended September 30, 2023 and other risks and uncertainties discussed from time to time in the Company’s filings with the U.S. Securities and Exchange Commission. Any forward-looking statement made in this presentation speaks only as of the date on which it is made. The Company undertakes no obligation to publicly update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise. References in this presentation: 1. All information is as of September 30, 2023, unless otherwise noted. 2. Annualized straight-line Base Rent (“ABR” or “Rent”) and the statistics based on ABR are calculated based on our current portfolio as of September 30, 2023. 3. Dividends are set by the Board of Directors and declared on a quarterly basis and there can be no assurances as to the likelihood or amount of dividends in the future. 4. A credit rated, or investment grade rated tenant (a tenant carrying a rating of BBB-, Baa3 or NAIC-2 or higher) is a tenant or the parent of a tenant with a credit rating from S&P Global Ratings, Moody’s Investors Service, Fitch Ratings or the National Association of Insurance Commissioners (NAIC).

24 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Non-GAAP Financial Information Our reported results are presented in accordance with accounting principles generally accepted in the United States of America (“GAAP”). We also disclose Funds From Operations (“FFO”), Adjusted Funds From Operations (“AFFO”) and Pro Forma Earnings Before Interest, Taxes, Depreciation and Amortization (“Pro Forma EBITDA”), all of which are non-GAAP financial measures. We believe these non-GAAP financial measures are useful to investors because they are widely accepted industry measures used by analysts and investors to compare the operating performance of REITs. FFO, AFFO, and Pro Forma EBITDA do not represent cash generated from operating activities and are not necessarily indicative of cash available to fund cash requirements; accordingly, they should not be considered alternatives to net income as a performance measure or cash flows from operations as reported on our statement of cash flows as a liquidity measure and should be considered in addition to, and not in lieu of, GAAP financial measures. We compute FFO in accordance with the definition adopted by the Board of Governors of the National Association of Real Estate Investment Trusts, or NAREIT. NAREIT defines FFO as GAAP net income or loss adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries. To derive AFFO, we modify the NAREIT computation of FFO to include other adjustments to GAAP net income related to non-cash revenues and expenses such as loss on extinguishment of debt, amortization of above- and below-market lease related intangibles, straight-line rental revenue, amortization of deferred financing costs, non-cash compensation, and other non-cash income or expense. Such items may cause short-term fluctuations in net income but have no impact on operating cash flows or long-term operating performance. We use AFFO as one measure of our performance when we formulate corporate goals. To derive Pro Forma EBITDA, GAAP net income or loss is adjusted to exclude extraordinary items (as defined by GAAP), net gain or loss from sales of depreciable real estate assets, impairment write-downs associated with depreciable real estate assets and real estate related depreciation and amortization, including the pro rata share of such adjustments of unconsolidated subsidiaries, non-cash revenues and expenses such as straight-line rental revenue, amortization of deferred financing costs, loss on extinguishment of debt, above- and below-market lease related intangibles, non-cash compensation, and other non-cash income or expense. Cash interest expense is also excluded from Pro Forma EBITDA, and GAAP net income or loss is adjusted for the annualized impact of acquisitions, dispositions and other similar activities. FFO is used by management, investors and analysts to facilitate meaningful comparisons of operating performance between periods and among our peers primarily because it excludes the effect of real estate depreciation and amortization and net gains or losses on sales, which are based on historical costs and implicitly assume that the value of real estate diminishes predictably over time, rather than fluctuating based on existing market conditions. We believe that AFFO is an additional useful supplemental measure for investors to consider because it will help them to better assess our operating performance without the distortions created by other non-cash revenues or expenses. We also believe that Pro Forma EBITDA is an additional useful supplemental measure for investors to consider as it allows for a better assessment of our operating performance without the distortions created by other non-cash revenues, expenses or certain effects of the Company’s capital structure on our operating performance. FFO, AFFO, and Pro Forma EBITDA may not be comparable to similarly titled measures employed by other companies.

25 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Statement of Operations Alpine Income Property Trust, Inc. Consolidated Statements of Operations (Unaudited) (In thousands, except share, per share and dividend data) 1. Includes the weighted average impact of 1,703,494 shares underlying OP units including (i) 1,223,854 shares underlying OP Units issued to CTO Realty Growth, Inc. and (ii) 479,640 shares underlying OP Units issued to an unrelated third party. Three Months Ended Nine Months Ended September 30, 2023 September 30, 2022 September 30, 2023 September 30, 2022 Revenues: Lease Income $ 11,447 $ 11,520 $ 33,951 $ 33,599 Interest Income from Commercial Loan Investments 112 — 112 — Total Revenues 11,559 11,520 34,063 33,599 Operating Expenses: Real Estate Expenses 1,722 1,816 4,731 4,193 General and Administrative Expenses 1,652 1,460 4,823 4,370 Provision for Impairment 2,864 — 2,864 — Depreciation and Amortization 6,528 5,866 19,286 17,232 Total Operating Expenses 12,766 9,142 31,704 25,795 Gain of Disposition of Assets 2,586 11,611 7,782 27,248 Gain (Loss) on Extinguishment of Debt — (284) 23 (284) Net Income from Operations 1,379 13,705 10,164 34,768 Investment and Other Income 125 9 226 9 Interest Expense (2,443) (2,544) (7,494) (6,347) Net Income (Loss) (939) 11,170 2,896 28,430 Less: Net Income (Loss) Attributable to Noncontrolling Interest (102) 1,400 314 3,572 Net Income (Loss) Attributable to Alpine Income Property Trust, Inc. $ (837) $ 9,770 $ 2,582 $ 24,858 Per Common Share Data: Net Income (Loss) Basic $ (0.06) $ 0.82 $ 0.18 $ 2.11 Diluted $ (0.05) $ 0.72 $ 0.16 $ 1.84 Weighted Average Number of Common Shares: Basic 13,946,194 11,888,171 14,001,774 11,799,151 Diluted1 15,649,688 13,591,665 15,705,268 13,502,645 Dividends Declared and Paid $ 0.275 $ 0.275 $ 0.825 $ 0.815

26 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Non-GAAP Financial Measures Reconciliation Alpine Income Property Trust, Inc. Non-GAAP Financial Measures Funds From Operations and Adjusted Funds From Operations (Unaudited) (In thousands, except per share data) Three Months Ended Nine Months Ended September 30, 2023 September 30, 2022 September 30, 2023 September 30, 2022 Net Income (Loss) $ (939) $ 11,170 $ 2,896 $ 28,430 Depreciation and Amortization 6,528 5,866 19,286 17,232 Provision for Impairment 2,864 — 2,864 — Gains on Disposition of Assets (2,586) (11,611) (7,782) (27,248) Funds from Operations $ 5,867 $ 5,425 $ 17,264 $ 18,414 Adjustments: Gain (Loss) on Extinguishment of Debt — 284 (23) 284 Amortization of Intangible Assets and Liabilities to Lease Income (110) (78) (299) (248) Straight-Line Rent Adjustment (112) (209) (386) (737) COVID-19 Rent Repayments — — — 45 Non-Cash Compensation 79 79 238 236 Amortization of Deferred Financing Costs to Interest Expense 179 150 530 407 Other Non-Cash Expense 29 25 86 72 Adjusted Funds from Operations $ 5,932 $ 5,676 $ 17,410 $ 18,473 FFO per Diluted Share $ 0.37 $ 0.40 $ 1.10 $ 1.36 AFFO per Diluted Share $ 0.38 $ 0.42 $ 1.11 $ 1.37

27 © 2023 Alpine Income Property Trust, Inc. | alpinereit.com Net Debt-to-EBITDA Pro Forma Reconciliation Alpine Income Property Trust, Inc. Non-GAAP Financial Measures Reconciliation of Net Debt to Pro Forma EBITDA (Unaudited) (In thousands) Three Months Ended September 30, 2023 Net Income (Loss) $ (939) Adjustments: Depreciation and Amortization 6,528 Provision for Impairment 2,864 Gains on Disposition of Assets (2,586) Straight-Line Rent Adjustment (112) Non-Cash Compensation 79 Amortization of Deferred Financing Costs to Interest Expense 179 Amortization of Intangible Assets and Liabilities to Lease Income (110) Other Non-Cash (Income) Expense 29 Interest Expense, net of Deferred Financing Costs Amortization 2,264 EBITDA $ 8,196 Annualized EBITDA $ 32,784 Pro Forma Annualized Impact of Current Quarter Acquisitions and Dispositions, Net1 949 Pro Forma EBITDA $ 33,733 Total Long-Term Debt $ 249,099 Financing Costs, Net of Accumulated Amortization 901 Cash and Cash Equivalents (6,265) Restricted Cash (11,166) Net Debt $ 232,569 Net Debt to Pro Forma EBITDA 6.9x 1. Reflects the pro forma annualized impact on Annualized EBITDA of the Company’s acquisition and disposition activities during the three months ended September 30, 2023.

Investor Inquiries: Matthew M. Partridge, Chief Financial Officer, (407) 904-3324, mpartridge@alpinereit.com

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Document and Entity Information	Oct. 19, 2023
Cover [Abstract]
Document Type	8-K
Document Period End Date	Oct. 19, 2023
Entity File Number	001-39143
Entity Registrant Name	ALPINE INCOME PROPERTY TRUST, INC.
Entity Incorporation, State or Country Code	MD
Entity Tax Identification Number	84-2769895
Entity Address, Address Line One	369 N. New York Avenue
Entity Address, Adress Line Two	Suite 201
Entity Address, City or Town	Winter Park
Entity Address, State or Province	FL
Entity Address, Postal Zip Code	32789
City Area Code	407
Local Phone Number	904-3324
Written Communications	false
Soliciting Material	false
Pre-commencement Tender Offer	false
Pre-commencement Issuer Tender Offer	false
Title of 12(b) Security	Common Stock, $0.01 Par Value
Trading Symbol	PINE
Security Exchange Name	NYSE
Entity Emerging Growth Company	true
Entity Ex Transition Period	true
Entity Central Index Key	0001786117
Amendment Flag	false