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Location: Millbrook, N.Y.
The Skinny: Despite the handsome and classic architecture, the main house on this sprawling country estate in Upstate New York was actually built in 1988. The detailing, aside from the rope lights in the kitchen and tiling in the bathroom, certainly belies the house's youth and the old-money landscaping, with mature trees and worn wood fences, helps to keep up the act. The estate's 149 acres allow for great privacy, but that space also holds some spectacular equestrian facilities, including an "18-stall barn, a 20,000 square foot indoor ring and 2 additional outdoor rings." The humans aren't short on amenities either, with a swimming pool, a tennis court, an automated skeet shooting system, a skating rink, motorcross track, home theater, gym, spa, and indoor basketball court. Plus there are two additional houses—a 3,200-square-foot guest house and a caretaker's cottage—to complement the 15-room, six-bedroom main house. With all this taken into account, it's no wonder the staggering compound is asking $27M.
· Sky Blue Farm [Houlihan Lawrence]