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Location: Head of the Harbor, N.Y.
The Skinny: One of Long Island's great historic estates, East Farm began as a family homestead in 1689, with a farmhouse built in 1710. Through the years, various additions and outbuildings were added to the property, including the substantial alterations performed in the early 1900s by former owner and noted estate architect Archibald Brown. In 1993, the entire 30-acre farm was added to the National Register of Historic Places, but by 1999, a new owner was proposing radical changes. The existing house was relocated to the edge of the property, the Brown-designed additions were removed, and it was renamed the "Wine Tasting House." While preservationists rightly objected to the demolition of the Brown additions, many were also pleased that the classic estate was not subdivided and developed as multiple home sites. A 26,500-square-foot megamansion rose on the original site, complete with indoor and outdoor swimming pools, a marble terrace, a rooftop deck, and a lighthouse-like turret. Now listed for $26.5M, the property also boasts a pair of vineyards, a tennis court, and a historic 3,000-square-foot guest house.