Revenue Recognition - Disaggregation of Revenue (Details) - USD ($) $ in Thousands	3 Months Ended								12 Months Ended
	Dec. 31, 2019	Sep. 30, 2019	Jun. 30, 2019	Mar. 31, 2019	Dec. 31, 2018	Sep. 30, 2018	Jun. 30, 2018	Mar. 31, 2018	Dec. 31, 2019	Dec. 31, 2018	Dec. 31, 2017
Disaggregation of Revenue [Line Items]
Total revenues	$ 439,565	$ 504,790	$ 538,432	$ 420,924	$ 445,939	$ 513,869	$ 481,488	$ 428,966	$ 1,903,711	$ 1,870,262	$ 1,807,476
Tobacco
Disaggregation of Revenue [Line Items]
Total revenues									1,114,840	1,111,094	1,080,950
Tobacco | Core Discount Brands - Pyramid, Grand Prix, Liggett Select, Eve and EAGLE 20’s
Disaggregation of Revenue [Line Items]
Total revenues									1,008,050	1,005,071	969,796
Tobacco | Other Brands
Disaggregation of Revenue [Line Items]
Total revenues									106,790	106,023	111,154
Real Estate
Disaggregation of Revenue [Line Items]
Total revenues									788,871	759,168	727,364
Total real estate revenues									788,871	759,168	727,364
Real Estate | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									376,600	366,032	401,304
Real Estate | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									171,677	172,348	175,201
Real Estate | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									126,181	114,788	90,758
Real Estate | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									114,413	106,000	60,101
Real Estate | Commission and other brokerage income
Disaggregation of Revenue [Line Items]
Total real estate revenues									669,489	651,171	633,093
Real Estate | Commission and other brokerage income | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									293,009	285,325	332,319
Real Estate | Commission and other brokerage income | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									164,724	166,100	168,834
Real Estate | Commission and other brokerage income | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									106,587	99,720	79,547
Real Estate | Commission and other brokerage income | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									105,169	100,026	52,393
Real Estate | Development marketing
Disaggregation of Revenue [Line Items]
Total real estate revenues									72,925	64,287	52,061
Real Estate | Development marketing | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									48,850	48,072	37,761
Real Estate | Development marketing | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	252	402
Real Estate | Development marketing | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									19,594	15,068	11,211
Real Estate | Development marketing | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									4,481	895	2,687
Real Estate | Property management income
Disaggregation of Revenue [Line Items]
Total real estate revenues									35,461	33,350	31,924
Real Estate | Property management income | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									34,741	32,635	31,224
Real Estate | Property management income | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									720	715	700
Real Estate | Property management income | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Property management income | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Title fees
Disaggregation of Revenue [Line Items]
Total real estate revenues									6,233	5,281	5,265
Real Estate | Title fees | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Title fees | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									6,233	5,281	5,265
Real Estate | Title fees | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Title fees | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Total Douglas Elliman Realty revenue
Disaggregation of Revenue [Line Items]
Total real estate revenues									784,108	754,089	722,343
Real Estate | Total Douglas Elliman Realty revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									376,600	366,032	401,304
Real Estate | Total Douglas Elliman Realty revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									171,677	172,348	175,201
Real Estate | Total Douglas Elliman Realty revenue | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									126,181	114,788	90,758
Real Estate | Total Douglas Elliman Realty revenue | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									109,650	100,921	55,080
Real Estate | Other real estate revenues
Disaggregation of Revenue [Line Items]
Total real estate revenues									4,763	5,079	5,021
Real Estate | Other real estate revenues | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Other real estate revenues | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Other real estate revenues | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues									0	0	0
Real Estate | Other real estate revenues | West
Disaggregation of Revenue [Line Items]
Total real estate revenues									$ 4,763	$ 5,079	$ 5,021