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Location: Alton, N.H.
The Skinny: There's no bulk discount for buying both of the homes on this gargantuan estate, which was built on the strangely enduring appeal of NASCAR racing as tapped into by its owner, New Hampshire Motor Speedway founder Bob Bahre: the ask is a record-breaking $49M all in, and $24M and $25M respectively for putting the homes on a separate tab. The luxe compound on the shores of Lake Winnipesaukee certainly seems like the sort of place a guy who made his fortune on car racing would build, with a helipad, a giant entertainment barn, and a grotto (there's always a grotto). The expansive spread includes 63,000 square feet of living space, with 12 bedrooms and 14 bathrooms, and more than 16 acres of land chockablock with tennis courts, boathouses, and an infinity pool (there's always an infinity pool). According to local media reports, Bahre is looking to downsize, which, given the size of this estate, won't be hard—even the recently sold Fleur de Lys estate in Los Angeles topped out at "just" 50,000 square feet.