Revenue Recognition - Disaggregation of Revenue (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2018	Mar. 31, 2017
Tobacco
Disaggregation of Revenue [Line Items]
Total tobacco revenues	$ 267,116	$ 257,454
Tobacco | Core Discount Brands - Pyramid, Grand Prix, Liggett Select, Eve and EAGLE 20’s
Disaggregation of Revenue [Line Items]
Total tobacco revenues	241,531	227,572
Tobacco | Other Brands
Disaggregation of Revenue [Line Items]
Total tobacco revenues	25,585	29,882
Real Estate
Disaggregation of Revenue [Line Items]
Total real estate revenues	161,850	157,754
Real Estate | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	79,156	97,446
Real Estate | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	33,990	24,740
Real Estate | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	24,691	26,023
Real Estate | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	24,013	9,545
Real Estate | Commission and other brokerage income
Disaggregation of Revenue [Line Items]
Total real estate revenues	138,896	134,504
Real Estate | Commission and other brokerage income | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	60,408	80,819
Real Estate | Commission and other brokerage income | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	32,678	23,630
Real Estate | Commission and other brokerage income | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	24,398	22,928
Real Estate | Commission and other brokerage income | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	21,412	7,127
Real Estate | Development marketing
Disaggregation of Revenue [Line Items]
Total real estate revenues	11,220	12,389
Real Estate | Development marketing | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	10,610	9,014
Real Estate | Development marketing | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	123	79
Real Estate | Development marketing | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	293	3,095
Real Estate | Development marketing | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	194	201
Real Estate | Property management income
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,338	7,783
Real Estate | Property management income | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,138	7,613
Real Estate | Property management income | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	200	170
Real Estate | Property management income | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Property management income | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Title fees
Disaggregation of Revenue [Line Items]
Total real estate revenues	989	861
Real Estate | Title fees | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Title fees | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	989	861
Real Estate | Title fees | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Title fees | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Total Douglas Elliman Realty revenue
Disaggregation of Revenue [Line Items]
Total real estate revenues	159,443	155,537
Real Estate | Total Douglas Elliman Realty revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	79,156	97,446
Real Estate | Total Douglas Elliman Realty revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	33,990	24,740
Real Estate | Total Douglas Elliman Realty revenue | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	24,691	26,023
Real Estate | Total Douglas Elliman Realty revenue | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	21,606	7,328
Real Estate | Other real estate revenues
Disaggregation of Revenue [Line Items]
Total real estate revenues	2,407	2,217
Real Estate | Other real estate revenues | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Other real estate revenues | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Other real estate revenues | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0
Real Estate | Other real estate revenues | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	$ 2,407	$ 2,217