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The Housing Market Correction Is Here. The Reset Isn't.05.19.2026

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  For over 25 years, I have analyzed housing and macroeconomic trends and how they shape real estate markets across New England. Following its peak in the fourth quarter of 2022, I expected the housing market to follow a more familiar correction pattern. As affordability spiked, prices would [...]

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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 Marthas Vineyard, just set a new sales record -- trading for $2,400,000. Asked what makes this property so attractive, heres what brokers Slater Anderson and Terry Boyle had to say about it: location, history, legacy.  

LOCATION

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.

HISTORIC PROPERTY

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.  

LEGACY POTENTIAL

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 didnt 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.

Want to see more? Watch here

 

ADDITIONAL LANDVEST PROJECTS ON CUTTYHUNK

[gallery link="file" size="medium" ids="108813,108723,108733,108753,108743,108713"]  

Want to get more of the inside scoop,
or check out a great property?

Contact us:

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

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