Better Homes Real Estate

55 Winterset DriveChatham, MA 02633Price: $2,295,000

  • Price: $2,295,000
  • Est. Mortgage of $/month
  • 108 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 7.32% last updated on Oct 22, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $2,295,000List Price
  • 4Bedrooms
  • 4Bathrooms
  • 4,066Square Feet

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Renovated and expanded Contemporary Cape at the end of a cul-de-sac on just under two acres allows for a unique amount of privacy while being less than a five minute drive to Chatham Village, Chatham Lighthouse, the Chatham Bars Inn and all that Chatham has to offer. As part of Great Hill Estates, this home has deeded rights to Lover's Lake for swimming, kayaking and canoeing. This home offers large open spaces perfect for entertaining and large gatherings. The first floor has a family room with vaulted beamed ceiling and wood burning fireplace open to a kitchen with large island and dining area, another large living room with gas fireplace open to a wraparound deck for grilling, dining and enjoying the views of nature looking out over the property. Enjoy a first floor primary with ensuite bathroom including laundry and a half bath. Upstairs are two more bedrooms, one as a second primary bedroom with sitting area and fireplace, another bedroom, and a full bath. The lower level has a bedroom, a full bath, second laundry, and walk-out access to a stone patio with custom stone seating area and a built-in gas fire-pit. Features including central a/c, hardwood floors, two car attached garage, brand new Bosch heating system and newer roof. Just steps away from the Cape Cod Rail Trail Bike Path, tennis courts, and pickleball courts. Home is being offered fully furnished.

Property Details of 55 Winterset Drive

Property Details

Interior Features

Exterior Features

Utilities and Appliances

Listed by Janet Stuart of Coldwell Banker Realty

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This site was last updated October 28, 2026 7:24 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

Better Homes and Gardens Real Estate | The Shanahan Group has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

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