Revenue Recognition - Disaggregation of Revenue (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2020	Jun. 30, 2019	Jun. 30, 2020	Jun. 30, 2019
Tobacco
Disaggregation of Revenue [Line Items]
Revenues	$ 312,510	$ 294,501	$ 599,579	$ 551,257
Tobacco | Core Discount Brands - EAGLE 20’s, PYRAMID, GRAND PRIX, LIGGETT SELECT, and EVE
Disaggregation of Revenue [Line Items]
Revenues	283,951	267,277	542,166	500,383
Tobacco | Other Brands
Disaggregation of Revenue [Line Items]
Revenues	28,559	27,224	57,413	50,874
Real estate
Disaggregation of Revenue [Line Items]
Total real estate revenues	133,250	243,931	300,669	408,099
Real estate | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	50,125	138,936	117,840	224,962
Real estate | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	36,215	40,521	71,419	72,255
Real estate | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	25,979	31,760	62,879	57,421
Real estate | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	20,931	32,714	48,531	53,461
Real estate | Commission brokerage income
Disaggregation of Revenue [Line Items]
Total real estate revenues	114,748	207,158	255,459	345,448
Real estate | Commission brokerage income | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	35,861	104,301	85,970	169,980
Real estate | Commission brokerage income | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	35,631	39,880	70,355	70,991
Real estate | Commission brokerage income | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	23,232	31,324	53,410	54,295
Real estate | Commission brokerage income | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	20,024	31,653	45,724	50,182
Real estate | Development marketing
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,506	23,176	23,761	37,199
Real estate | Development marketing | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	5,173	22,718	13,624	34,104
Real estate | Development marketing | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0	0	0
Real estate | Development marketing | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	2,747	436	9,469	3,066
Real estate | Development marketing | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	586	22	668	29
Real estate | Property management revenue
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,832	10,218	17,611	18,569
Real estate | Property management revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	8,617	10,048	17,179	18,215
Real estate | Property management revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	215	170	432	354
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	843	2,400	1,699	3,633
Real estate | Title fees | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	474	1,869	1,067	2,663
Real estate | Title fees | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	369	471	632	910
Real estate | Title fees | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	0	0	60
Real estate | Title fees | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	0	60	0	0
Real estate | Total Douglas Elliman revenue
Disaggregation of Revenue [Line Items]
Total real estate revenues	132,929	242,952	298,530	404,849
Real estate | Total Douglas Elliman revenue | New York City
Disaggregation of Revenue [Line Items]
Total real estate revenues	50,125	138,936	117,840	224,962
Real estate | Total Douglas Elliman revenue | Northeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	36,215	40,521	71,419	72,255
Real estate | Total Douglas Elliman revenue | Southeast
Disaggregation of Revenue [Line Items]
Total real estate revenues	25,979	31,760	62,879	57,421
Real estate | Total Douglas Elliman revenue | West
Disaggregation of Revenue [Line Items]
Total real estate revenues	20,610	31,735	46,392	50,211
Real estate | Other real estate revenues
Disaggregation of Revenue [Line Items]
Total real estate revenues	321	979	2,139	3,250
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	$ 321	$ 979	$ 2,139	$ 3,250