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4 Beds
4 Baths
4,066 sqft

$2,295,000

55 Winterset Drive, Chatham MA, 02633

Price per sqft$564.44
Built in1970
Property size4,066 sqft
Property typeResidential

Overview

Active

Listed Jul 12, 2026

Updated 19h ago

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.

$15,269/mo

Est. mortgage payment based on a $2,295,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
22603375

Interior Features

Bedrooms
4
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.94 Acres

Other Property Details

Taxes
$5,655
Tax Frequency
Annually
Association Fee Frequency
Yearly
Garage
Yes

Courtesy of Coldwell Banker Realty, Janet Stuart

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. (CCIMLS). Real estate listings provided by CCIMLS and held by brokerage firms other than Colleen and Sabrina Riley are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. This site was last updated 10/24/2026. Neither the listing broker nor Colleen and Sabrina Riley shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal.

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