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Location: Chappaqua, N.Y.
The Skinny: You've got to hand it to this country estate in N.Y.'s Westchester County: it's outrageously opulent. Because let's face it, doing opulence—hardcore, money-to-burn, next-level New Gilded Age-style opulence—right is tough. There's a fine, but distinct, line between luxury and opulence, and it takes grit and a pile of lucre to get from one to the other. For instance, possessing a full-size outdoor basketball court is totally luxurious, and while plenty of people would stop there, satisfied with a job of conspicuous consumption well-done, the owners of this house took that next, all-important step across the threshold into opulence; they built themselves an indoor basketball court as well. An infinity pool is luxurious; building a pool cottage so you can watch TV after a swim without that tedious walk all the way back to the main house is totally opulent. And it goes without saying that having a 20,000 square foot home with two fitness rooms that sits on 87 acres (including a private lake) is country-squire opulent. The downside to all this opulence? Trying to sell a home like this: it's been on and off the market since 2010, with the original $27.5M ask drifting slowly down to the current asking price of $19.9M.