37. Alan Jackson’s House

Price: $4.9 million

Location: 6500 Coconut Ridge, Smithville, TN

Square Footage: 6,114 Sq Ft.

If you need proof that the housing market is fucked, look no further than the list price for country crooner Alan Jackson’s insane waterfront home. In a different economy the asking price for this estate would definitely be 8 figures for all of these features: in addition to the 5 br main house there’s a 4 bedroom guest house, a 1 bedroom cabin, 2 story houseboat with private docking, and a garage complete with a rooftop helipad. Oh, and there’s a 1 acre building site on top of all of that. No wonder Jackson and his wife think the estate’s too much land for them now that all their kids have left the nest.