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Cuttyhunk Island, part of the Elizabeth Islands off the southern coast of Massachusetts is located between Buzzards Bay and Vineyard Sound. Just 550± acres with a year-round population of approximately 30 residents, the quaint island offers a quiet, beautiful, ocean environment perfect for fishing, sailing, reading and relaxing. The island’s population swells as summer residents, vacationers and boaters head over when the weather warms. Pleasantries on the island include brunches at the Fishing Club, seasonal food shacks by the pier, and small yacht club that primarily provides activities for children. The offering includes a stately custom main residence (Winter House), a one-story seasonal residence (Annex), a two-story seasonal residence (Rose Cottage), a large barn, and two accessory structures on 7.90± acres (surveyed) with impressive panoramic water views to the north, east, and south.
  • Winter House includes 8,221± square feet of living area (measured) with eight bedrooms, eight in-suite full bathrooms, one half bathroom, and 10 fireplaces (not currently functional).
  • Winter House offers an enclosed porch with 703± square feet of area and a large 3,000± square foot unfinished basement
  • Ceiling heights within Winterhouse range from 10’-4” on the first floor to 8’-0” on the third floor
  • The Annex includes 768± square feet of living area with one bedroom and one full bathroom
  • Rose Cottage has 819± square feet of living area with three bedrooms and one full bathroom
  • The three residences were built circa 1917
  • Much of the site is open lawn area with a long, paved driveway that extends through the property
  • Footpaths lead to Broadway and to Cuttyhunk's Avalon Inn
  • A 2.63± acre Conservation Restriction runs along the western boundary of the property

Property Details

Slater Anderson




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