Revenue Recognition - Disaggregation of Revenue (Details) - USD ($) $ in Thousands	3 Months Ended								12 Months Ended
	Dec. 31, 2020	Sep. 30, 2020	Jun. 30, 2020	Mar. 31, 2020	Dec. 31, 2019	Sep. 30, 2019	Jun. 30, 2019	Mar. 31, 2019	Dec. 31, 2020	Dec. 31, 2019	Dec. 31, 2018
Disaggregation of Revenue [Line Items]
Total revenues	$ 554,590	$ 547,831	$ 445,760	$ 454,488	$ 439,565	$ 504,790	$ 538,432	$ 420,924	$ 2,002,669	$ 1,903,711	$ 1,870,262
Tobacco
Disaggregation of Revenue [Line Items]
Total revenues									1,204,501	1,114,840	1,111,094
Tobacco | Core Discount Brands - Eagle 20’s, Pyramid, Montego, Grand Prix, Liggett Select and Eve
Disaggregation of Revenue [Line Items]
Total revenues									1,133,660	1,040,419	1,026,370
Tobacco | Other Brands
Disaggregation of Revenue [Line Items]
Total revenues									70,841	74,421	84,724
Real Estate
Disaggregation of Revenue [Line Items]
Total revenues									798,168	788,871	759,168
Real Estate | New York City
Disaggregation of Revenue [Line Items]
Total revenues									247,075	376,600	366,032
Real Estate | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									227,937	171,677	172,348
Real Estate | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									182,485	126,181	114,788
Real Estate | West
Disaggregation of Revenue [Line Items]
Total revenues									140,671	114,413	106,000
Real Estate | Commission brokerage income
Disaggregation of Revenue [Line Items]
Total revenues									687,746	669,489	651,171
Real Estate | Commission brokerage income | New York City
Disaggregation of Revenue [Line Items]
Total revenues									186,229	293,009	285,325
Real Estate | Commission brokerage income | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									204,814	164,724	166,100
Real Estate | Commission brokerage income | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									160,404	106,587	99,720
Real Estate | Commission brokerage income | West
Disaggregation of Revenue [Line Items]
Total revenues									136,299	105,169	100,026
Real Estate | Development marketing
Disaggregation of Revenue [Line Items]
Total revenues									47,362	72,925	64,287
Real Estate | Development marketing | New York City
Disaggregation of Revenue [Line Items]
Total revenues									24,590	48,850	48,072
Real Estate | Development marketing | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									0	0	252
Real Estate | Development marketing | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									22,081	19,594	15,068
Real Estate | Development marketing | West
Disaggregation of Revenue [Line Items]
Total revenues									691	4,481	895
Real Estate | Property management revenue
Disaggregation of Revenue [Line Items]
Total revenues									35,115	35,461	33,350
Real Estate | Property management revenue | New York City
Disaggregation of Revenue [Line Items]
Total revenues									34,209	34,741	32,635
Real Estate | Property management revenue | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									906	720	715
Real Estate | Property management revenue | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Property management revenue | West
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Title fees
Disaggregation of Revenue [Line Items]
Total revenues									3,764	6,233	5,281
Real Estate | Title fees | New York City
Disaggregation of Revenue [Line Items]
Total revenues									2,047	0	0
Real Estate | Title fees | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									1,717	6,233	5,281
Real Estate | Title fees | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Title fees | West
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Total Douglas Elliman revenue
Disaggregation of Revenue [Line Items]
Total revenues									773,987	784,108	754,089
Real Estate | Total Douglas Elliman revenue | New York City
Disaggregation of Revenue [Line Items]
Total revenues									247,075	376,600	366,032
Real Estate | Total Douglas Elliman revenue | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									207,437	171,677	172,348
Real Estate | Total Douglas Elliman revenue | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									182,485	126,181	114,788
Real Estate | Total Douglas Elliman revenue | West
Disaggregation of Revenue [Line Items]
Total revenues									136,990	109,650	100,921
Real Estate | Other real estate revenues
Disaggregation of Revenue [Line Items]
Total revenues									24,181	4,763	5,079
Real Estate | Other real estate revenues | New York City
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Other real estate revenues | Northeast
Disaggregation of Revenue [Line Items]
Total revenues									20,500	0	0
Real Estate | Other real estate revenues | Southeast
Disaggregation of Revenue [Line Items]
Total revenues									0	0	0
Real Estate | Other real estate revenues | West
Disaggregation of Revenue [Line Items]
Total revenues									$ 3,681	$ 4,763	$ 5,079