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Location: Vineyard Haven, Mass.
The Skinny: Sequestered at the end of a long private drive on Martha's Vineyard's north shore, this 22-acre compound combines rural seclusion with the looks of a casual, clean-cut vacation escape. Three separate structures dot the landscape here—a main house, a guest house, and a "pond house"—all sharing 300 feet of private beach, accessed by a narrow boardwalk. The grounds feature rolling lawns, a private pond, and stone walls, while the three structures are left in varying states of casual disrepair, but with immaculately maintained interiors. Inland, the property also has a private tennis court and artist's studio. For $10.5M, this might be the ultimate expression of a casual, preppy form of luxury.
· 556 Chappaquonsett Road [Sotheby's]