55 Winterset Drive
Chatham, MA, 02633 $ 2,295,000
Bedrooms4 Baths3.1 Sq 4,066 Monthly Estimate*
$ 15,851
for $2,295,000 with 4 bedrooms and 3 full baths, 1 half bath. This 4,066 square foot home was built in 1970 on a lot size of 1.94.
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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FeaturesGeneralHeating Natural Gas
Cooling Central Air
Roof Asphalt Shingle
Appliances Natural Gas Water Heater
HOA Fee 75
Garage Spaces 2
Patio/Porch Features Deck Patio
Architectural Style Cape Cod Contemporary
Construction Materials Shingle Siding
Year Built 1970
Stories Count 3
Property Subtype Single Family Residence
Tax Year 2026
Assoc Fee Paid Per Annually
County Barnstable
Property Type Residential
Association Amenities Beach Access
HOA true
Attached Garage false
Subdivision Name Great Hills
Garage Y/N true
Total Rooms 8
Full Baths 3
Status Active
Directions Old Queen Anne Road to Winterset Drive house located at the end on the left.
City Chatham
MLS Area Chatham
Lot Size Units Acres
Lot Size Square Feet 84506
Tax Annual Amount 5655
Showing Instructions Call Listing Agent Janet Stuart at 617-515-3824 for all showings.
Building Area Units Square Feet
Standard Status Active
Tax Assessed Value 1540900
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InteriorInterior Amenities Central Vacuum Recessed Lighting
Basement Finished Full
Flooring Hardwood Carpet
Total Fireplaces 4
Air Conditioning Y/N true
Heating Y/N true
Half Baths 1
Total Bedrooms 4
Total Baths 4
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ExteriorFencing Partial
Parking Features Direct Access Garage Door Opener Off Street Paved
Lot Features Corner Lot
Water Source Public
Total Parking 14
Lot Size Area 1.94
Building Area Total 4066
Lot Size Acres 1.94
Waterfront Y/N false
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* Excluded FeaturesList ByJanet StuartListing Agent
Coldwell Banker RealtyBroker
janet.stuart@nemoves.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $15,851
- Monthly Property Taxes
- $471
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Chatham, MA
Average List Price $3,195,176
Percent of Sale Price 39%
About Chatham, MA 6,037 Population
-10% Since 2002
$ 69,389 Median Income
60.04 Median Age
13% Households with Children
Trends Information provided by ATTOM Data Solutions.
0 Elementary School
0 Middle School
Pricing History| Date | Price | Price Change | Description |
|---|
| 9/11/2026 | $2,295,000 | -3.97% | Price Down |
| 9/7/2026 | $2,390,000 | | Listed Price |