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Revenue Recognition - Disaggregation of Revenue (Details) - USD ($)
$ in Thousands
 3 Months Ended 6 Months Ended
Jun. 30, 2019
Jun. 30, 2018
Jun. 30, 2019
Jun. 30, 2018
Disaggregation of Revenue [Line Items]        
Revenues $ 538,432 $ 481,488 $ 959,356 $ 910,454
Tobacco        
Disaggregation of Revenue [Line Items]        
Revenues 294,501 274,833 551,257 541,949
Tobacco | Core Discount Brands - EAGLE 20’s, PYRAMID, GRAND PRIX, LIGGETT SELECT, and EVE        
Disaggregation of Revenue [Line Items]        
Revenues 267,277 248,370 500,383 489,901
Tobacco | Other Brands        
Disaggregation of Revenue [Line Items]        
Revenues 27,224 26,463 50,874 52,048
Real estate        
Disaggregation of Revenue [Line Items]        
Revenues 243,931 206,655 408,099 368,505
Total real estate revenues 243,931 206,655 408,099 368,505
Real estate | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 137,067 95,294 222,299 174,450
Real estate | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 42,450 45,460 74,978 79,450
Real estate | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,760 36,697 57,361 61,388
Real estate | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 32,654 29,204 53,461 53,217
Real estate | Commission brokerage income        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 207,158 179,411 345,448 318,307
Real estate | Commission brokerage income | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 104,301 76,175 169,980 136,583
Real estate | Commission brokerage income | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 39,880 43,228 70,991 75,906
Real estate | Commission brokerage income | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,324 31,909 54,295 56,307
Real estate | Commission brokerage income | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,653 28,099 50,182 49,511
Real estate | Development marketing        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 23,176 15,525 37,199 26,745
Real estate | Development marketing | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 22,718 10,559 34,104 21,169
Real estate | Development marketing | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 129 0 252
Real estate | Development marketing | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 436 4,788 3,066 5,081
Real estate | Development marketing | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 22 49 29 243
Real estate | Property management revenue        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 10,218 8,741 18,569 17,079
Real estate | Property management revenue | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 10,048 8,560 18,215 16,698
Real estate | Property management revenue | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 170 181 354 381
Real estate | Property management revenue | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Property management revenue | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Title fees        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 2,400 1,922 3,633 2,911
Real estate | Title fees | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Title fees | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 2,400 1,922 3,633 2,911
Real estate | Title fees | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Title fees | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Total Douglas Elliman revenue        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 242,952 205,599 404,849 365,042
Real estate | Total Douglas Elliman revenue | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 137,067 95,294 222,299 174,450
Real estate | Total Douglas Elliman revenue | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 42,450 45,460 74,978 79,450
Real estate | Total Douglas Elliman revenue | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,760 36,697 57,361 61,388
Real estate | Total Douglas Elliman revenue | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,675 28,148 50,211 49,754
Real estate | Other real estate revenues        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 979 1,056 3,250 3,463
Real estate | Other real estate revenues | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Other real estate revenues | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Other real estate revenues | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 0
Real estate | Other real estate revenues | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues $ 979 $ 1,056 $ 3,250 $ 3,463