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Revenue Recognition - Disaggregation of Revenue (Details) - USD ($)
$ in Thousands
 3 Months Ended 9 Months Ended
Sep. 30, 2019
Sep. 30, 2018
Sep. 30, 2019
Sep. 30, 2018
Disaggregation of Revenue [Line Items]        
Revenues $ 504,790 $ 513,869 $ 1,464,146 $ 1,424,323
Tobacco        
Disaggregation of Revenue [Line Items]        
Revenues 303,260 302,009 854,517 843,958
Tobacco | Core Discount Brands - EAGLE 20’s, PYRAMID, GRAND PRIX, LIGGETT SELECT, and EVE        
Disaggregation of Revenue [Line Items]        
Revenues 273,918 274,405 774,301 764,306
Tobacco | Other Brands        
Disaggregation of Revenue [Line Items]        
Revenues 29,342 27,604 80,216 79,652
Real estate        
Disaggregation of Revenue [Line Items]        
Revenues 201,530 211,860 609,629 580,365
Total real estate revenues 201,530 211,860 609,629 580,365
Real estate | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 88,485 103,907 310,784 278,357
Real estate | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 48,299 49,789 123,277 129,239
Real estate | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 32,622 30,579 89,983 91,967
Real estate | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 32,124 27,585 85,585 80,802
Real estate | Commission brokerage income        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 172,925 177,481 518,373 495,788
Real estate | Commission brokerage income | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 73,081 79,192 243,061 215,775
Real estate | Commission brokerage income | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 47,066 48,996 118,057 124,902
Real estate | Commission brokerage income | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 25,008 22,491 79,303 78,798
Real estate | Commission brokerage income | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 27,770 26,802 77,952 76,313
Real estate | Development marketing        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 18,526 24,677 55,725 51,422
Real estate | Development marketing | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 6,920 16,187 41,024 37,356
Real estate | Development marketing | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 0 0 0 252
Real estate | Development marketing | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 7,614 8,088 10,680 13,169
Real estate | Development marketing | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 3,992 402 4,021 645
Real estate | Property management revenue        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 8,668 8,147 27,237 25,226
Real estate | Property management revenue | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 8,484 8,528 26,699 25,226
Real estate | Property management revenue | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 184 (381) 538
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 1,049 1,174 4,682 4,085
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 1,049 1,174 4,682 4,085
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 201,168 211,479 606,017 576,521
Real estate | Total Douglas Elliman revenue | New York City        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 88,485 103,907 310,784 278,357
Real estate | Total Douglas Elliman revenue | Northeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 48,299 49,789 123,277 129,239
Real estate | Total Douglas Elliman revenue | Southeast        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 32,622 30,579 89,983 91,967
Real estate | Total Douglas Elliman revenue | West        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 31,762 27,204 81,973 76,958
Real estate | Other real estate revenues        
Disaggregation of Revenue [Line Items]        
Total real estate revenues 362 381 3,612 3,844
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 $ 362 $ 381 $ 3,612 $ 3,844