55 WINTERSET DRIVE, CHATHAM MA, 02633

$2,295,000

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Cape Cod MLS #22603375

Status: Price Change
Year Built: 1970
Total Rooms: 8
Full Bathrooms: 3
Bedrooms: 4
Half Bathrooms: 1
Waterview: No
To Beach: .1 miles to Lover's Lake beach mi.
Waterfront: No
Lot Size: 1.94 acres
Living Area: 4066 ft2
Price Change: 09/11/2026
Listing Date: 07/12/26 DOM: 109 days
Total Assessment: $1,540,900
Improvements Assessment: $1,152,900
Special Assessment: N/A
Annual Taxes: $5,655
Tax Year: 2026
Land Assessment: 0
Zoning: R60
Lead Paint: Unknown
Flood Zone: N/A

55 WINTERSET DRIVE, CHATHAM MA, 02633

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


General Information:

VILLAGE: Chatham
STYLE: Single Family Residence
HEAT/COOLING: Natural Gas
GARAGE: YES
BASEMENT:
Basement Type:
Convenient To: Bike Path, Cape Cod Rail Trail, Conservation Area, Golf Course, House of Worship, Major Highway, Marina, Medical Facility, Public Tennis, School, Shopping, Convenient to WaterBody 1: Lovers Lake, Convenient to WaterBody 2: Hardings Beach
Association: Yes - fee includes Beach Access

Exterior Features:

Exterior Features: Private Yard
Pool:
Dock: N
Siding:
Roof: Shingle, Asphalt

Interior Features:

Fireplace: 4
Flooring: Carpet, Hardwood

Interior Features: Eat-in Kitchen, Central Vacuum, Breakfast Bar, Recessed Lighting, Kitchen Island
Equipment/Appliances: Water Heater

Mechanical Features:

Heating/Cooling: Natural Gas
Utilities:

Listing Office Contact:


Listing Courtest of:
Coldwell Banker Realty
Listing Agent: Janet Stuart (617-515-3824)

55 WINTERSET DRIVE CHATHAM MA 02633 Property Information Last Updated October 28, 2026 at 11:45:19 PM EDT.

 

CCIAOR MLS IDX listing courtesy of Coldwell Banker Realty