Discover Your Cape Cod

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

  • Price: $2,295,000
  • Est. Mortgage of $/month
  • 98 Days on Market
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Federal 30-year interest rate: 7.4% last updated on Oct 15, 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
  • 1.94Acreage
  • 4,066Square Feet
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Set up high on approximately 2 acres in Chatham's Great Hill, this sun-drenched, wonderfully renovated 4-bedroom, 3.5-bath home offers deeded rights to Lovers Lake for swimming, kayaking and canoeing, along with privacy, space, and convenient access to the best of Chatham. The property is set at the end of a quiet cul-de-sac with treetop views, a private natural setting, and wraparound decks. The first floor features two great rooms with beamed ceilings and fireplaces, an open kitchen with granite countertops, island seating and a large dining area, a half bath, plus a primary bedroom with en-suite full bath, laundry, and great closet space. Upstairs is a second primary bedroom with walk-in closet, fireplace and sitting area, additional bedroom, and a full bath. The walkout lower level includes a good-sized fourth bedroom, full bath, full laundry, and access to a stone patio with gas fire pit and built-in stone seating. Hardwood floors, abundant windows and doors, central AC throughout, a 2-car garage with exterior access door, a brand-new Bosch heating system, and a new roof add to the home's appeal. Enjoy convenient access to Chatham Village, the bike path, and Chatham's beaches.

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Listed by Janet Stuart of Coldwell Banker Realty

broker reciprocity The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Cape Realty Group are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor Cape Realty Group shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless.

This site was last updated October 17, 2026 8:51 PM EDT. All properties are subject to prior sale, changes, or withdrawal.

Cape Realty 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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