Thomas D. Brown Real Estate Associates
Rentals 508-349-2700
300 Route 6
PO Box 2003
Truro, MA 02666

55 Winterset Drive Chatham MA 02633 | MLS #22603375

MLS #22603375 image #0
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.
Current real estate data for Single Family in Chatham as of Sep 20, 2026
59
Single Family Listed
120
Avg DOM
1,174
Avg $ / SqFt
$3,465,415
Avg List Price

Property Details

Price:
$2,295,000
MLS #:
22603375
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills
Neighborhood:
chatham
Listed Date:
Jul 12, 2026
Finished Sq Ft:
4,066
Total Sq Ft:
4,066
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
ChathamChathamGreat Hills

Schools

Interior

Appliances
Natural Gas, Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
4
Flooring
Hardwood, Carpet
Heating
Natural Gas
Interior Features
Central Vacuum, Recessed Lighting

Exterior

Association Amenities
Beach Access
Construction Materials
Shingle Siding
Fencing
Partial
Garage Spaces
2
Lot Features
Corner Lot
Parking Features
Direct Access, Garage Door Opener, Off Street, Paved
Parking Spots
14
Parking Total
14
Patio And Porch Features
Deck, Patio
Roof
Asphalt, Shingle
Stories
3

Financial

HOA Fee
$75
HOA Fee Frequency
Annually
Tax Year
2026
Taxes
$5,655

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Subdivisions in Chatham

Property Summary

    Located in the Great Hills subdivision, 55 Winterset Drive Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $2,295,000 and features 4 beds, 4 baths, and has approximately 4,066 square feet of living space, and was originally constructed in 1970. The current price per square foot is $564. The average price per square foot for Single Family listings in Chatham is $1,174. The average listing price for Single Family in Chatham is $3,465,415. To schedule a showing of MLS#22603375 at 55 Winterset Drive in Chatham, MA, contact your Thomas D Brown R E Associates agent at 508-487-1112.

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Raised in Orleans and now a resident of Truro, Lucy is extremely familiar with life on the Outer Cape. She is experienced in real estate sales on Cape Cod and has been involved in construction, development and real estate for over thirty-five years here on the Outer Cape. She presently handles all facets of marketing for both Brown Associates and Cape Vacation Rentals. Degree in Sales & Marketing; formerly associated with Nickerson Realty Corp. where she handled all phases of land development, a…

More About Lucy
55 Winterset Drive
Chatham, MA