Revenue Recognition (Disaggregation of Revenue) (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2020	Sep. 30, 2019	Sep. 30, 2020	Sep. 30, 2019
Tobacco
Disaggregation of Revenue [Line Items]
Revenues	$ 318,850	$ 303,260	$ 918,429	$ 854,517
Tobacco | Core Discount Brands - Eagle 20’s, Pyramid, Montego, Grand Prix, Liggett Select, and Eve
Disaggregation of Revenue [Line Items]
Revenues	300,487	283,621	864,880	798,272
Tobacco | Other Brands
Disaggregation of Revenue [Line Items]
Revenues	18,363	19,639	53,549	56,245
Real estate
Disaggregation of Revenue [Line Items]
Total real estate revenues	228,981	201,530	529,650	609,629
Real estate | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	56,302	88,485	174,142	310,784
Real estate | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	80,213	48,299	151,632	123,277
Real estate | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	49,447	32,622	112,326	89,983
Real estate | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	43,019	32,124	91,550	85,585
Real estate | Commission and other brokerage income - existing home sales
Disaggregation of Revenue [Line Items]
Total real estate revenues	187,831	172,925	443,290	518,373
Real estate | Commission and other brokerage income - existing home sales | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	43,039	73,081	129,009	243,061
Real estate | Commission and other brokerage income - existing home sales | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	58,909	47,066	129,264	118,057
Real estate | Commission and other brokerage income - existing home sales | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	43,883	25,008	97,293	79,303
Real estate | Commission and other brokerage income - existing home sales | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	42,000	27,770	87,724	77,952
Real estate | Commission and other brokerage income - development marketing
Disaggregation of Revenue [Line Items]
Total real estate revenues	10,669	18,526	34,430	55,725
Real estate | Commission and other brokerage income - development marketing | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	4,571	6,920	18,195	41,024
Real estate | Commission and other brokerage income - development marketing | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0	0	0
Real estate | Commission and other brokerage income - development marketing | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	5,564	7,614	15,033	10,680
Real estate | Commission and other brokerage income - development marketing | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	534	3,992	1,202	4,021
Real estate | Property management revenue
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,584	8,668	26,195	27,237
Real estate | Property management revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,334	8,484	25,513	26,699
Real estate | Property management revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	250	184	682	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	912	1,049	2,611	4,682
Real estate | Title fees | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	358	0	1,425	0
Real estate | Title fees | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	554	1,049	1,186	4,682
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	207,996	201,168	506,526	606,017
Real estate | Total Douglas Elliman revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	56,302	88,485	174,142	310,784
Real estate | Total Douglas Elliman revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	59,713	48,299	131,132	123,277
Real estate | Total Douglas Elliman revenue | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	49,447	32,622	112,326	89,983
Real estate | Total Douglas Elliman revenue | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	42,534	31,762	88,926	81,973
Real estate | Other real estate revenues
Disaggregation of Revenue [Line Items]
Total real estate revenues	20,985	362	23,124	3,612
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	20,500	0	20,500	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	$ 485	$ 362	$ 2,624	$ 3,612