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Location: Edgartown, Massachusetts

Price: Last listed for $9,350,000

The Martha's Vineyard whaling village turned blue-blood enclave of Edgartown, Massachusetts, is a showplace for classic New England coastal architecture, with plenty of shingles and widow's walks, but the most desirable real estate is determined by location, not architecture. This 0.19-acre estate on the coveted inner harbor waterfront has been on the market for several years without garnering a sale, and now the owners are getting restless. After more than 80 years of family stewardship, they've moved to auction the property. The six-bed, five-bath mini-compound will begin accepting bids on October 22, with the auction set to close a week later. Will the rare waterfront swimming pool be enough to drive bidding close to the previous $9,350,000 asking price?