Historic Island Estate
Sets Record Sale

Winter House on Cuttyhunk has Sold

Winter House on Cuttyhunk Aerial
Winter House on Cuttyhunk Island, one of the Elizabeth Islands off the south coast of Massachusetts and adjacent to Martha’s Vineyard, just set a new sales record — trading for $2,400,000. Asked what makes this property so attractive, here’s what brokers Slater Anderson and Terry Boyle had to say about it: location, history, legacy.


Cuttyhunk Aerial
Just 550± acres with a year-round population of approximately 30 residents, the quaint island is a quiet, beautiful, ocean environment perfect for fishing, sailing, reading and relaxing. Sited on 7.90± acres high above the ocean, Winter House offers a long sweeping lawn and panoramic water views to the north, east, and south. Properties listed for sale on Cuttyhunk are rare, and large available estate properties (almost) unheard of.


Winter House on Cuttyhunk MA2072-4_13_CC
Winter House on Cuttyhunk, MA2072-4_12_CC Winter House on Cuttyhunk, MA2072-4_11_CC

Winter House was built a century ago by Edgartown resident, William Madison Wood, President of the American Woolen Company, as a wedding present for his son. Though used mainly in the summer, the house was equipped for year-round living, thus the name Winter House. Offered to the open market for the first time, multiple bids to purchase were submitted. Winter House was ultimately sold to a buyer with family ties to the property and island.


Winter House on Cuttyhunk, MA2072-4_3_CC
Winter House had sat shuttered for many years. There had been interest in converting the historic house into a resort by a Vineyard hotelier whose projects included Winnetu Oceanside Resort, Mattakesett Properties in Katama and the Nantucket Hotel and Resort. The proposed development didn’t gain traction within the island community, so Winter House was put up for sale to the general market.
Winter House on Cuttyhunk, MA2072-4_22_CC

This landmark property was purchased by a family who intends to renovate the stately home for their own use. We hope they, like previous owners, create generations of memories at Winter House.

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Contact us:

Slater Anderson | sanderson@landvest.com | 617-357-8990
Terry Boyle | tboyle@landvest.com | 617-357-0432