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Location: West Falmouth, Mass.
The Skinny: This shingle-style estate on Frederick Law Olmsted-planned Chapoquoit Island is the pinnacle of preppy summering. Located within a private association, with easy access to the prime sailing grounds of Buzzards Bay, the five-bedroom cottage sprawls over 3,800 square feet and enjoys dazzling water views from nearly every room. The listing focuses on the cottage's beautiful exterior, saving only one HDR-heavy photo for the interior, so its safe to assume that plenty of work is necessary on the inside to bring this 1902 beauty up to modern standards. Listed for $4.5M, the house sits on 1.43 acres, with a pond and a coveted private dock.
· 140 Associates Rd [Realtor.com]