55 WINTERSET DRIVE, CHATHAM MA, 02633

$2,390,000

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Cape Cod MLS #22603375

Status: Active
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
Listing Date: 07/12/26 DOM: 42 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

OPEN HOUSE: Sun, August 23, 11:30 AM - 12:30 PM

55 WINTERSET DRIVE, CHATHAM MA, 02633

Spectacular four bedroom home set on almost 2 acres in sought-after Great Hill Estates.With deeded rights to private Lovers Lake perfect for swimming, kayaking and fishing. Located at the end of a quiet cul-de-sac, this home offers privacy and views of nature at every turn. Dramatic cathedral ceilings, 4 fireplaces, open floor plan & wraparound deck with elevated views of the expansive property all perfect for entertaining and large family gatherings. The 1st floor has two large family rooms w/ soaring ceilings and floor to ceiling fireplaces, kitchen with granite and island open to a dining area, a primary suite with en-suite bath and laundry and a half bath. Upstairs is a second primary suite w/ fireplace and sitting area, an additional bedroom and a full bath. The walkout lower level has a bedroom, full bath, another washer/dryer and leads to a stone patio with fire pit. Close to Chatham Village, bike path and Chatham beaches. Home is being offered fully furnished if desired.


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 August 23, 2026 at 9:45:17 PM EDT.

 

CCIAOR MLS IDX listing courtesy of Coldwell Banker Realty