55 Winterset Drive
Chatham, MA, 02633
$2,495,000
Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham’s most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover’s Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick fireplaces, open concept kitchen/dining room, multiple french doors, and wrap-around decks invite the outside in as sunlight & breezes waft throughout. A 1st floor primary bdrm with ample closets, ensuite bath & laundry complements the spectacular 1st floor living. Upstairs a second primary bdrm with fireplace & walk-in closet, a guest room & bath offer flexibility. The daylight lower level consists of a 4th bdrm, bath, laundry area & an unfinished room that opens to a patio with a custom masonry stone bench & fire pit. The sprawling lawn & stunning stone walls provide the perfect backdrop for a future swimming pool, tennis court & guest house or ADU. Plus potential to subdivide a 2nd lot. Minutes to the bike path, Chatham’s bustling village & ocean beaches. May be sold furnished.
Current real estate data for Single Family in Chatham as of Jun 26, 2025
78
Single Family Listed
124
Avg DOM
$2,905,129
Avg List Price
Property Details
Price:
$2,495,000
MLS #:
22502257
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Great Hills Estates
Listed Date:
May 6, 2025
Total Sq Ft:
4,072
Lot Size:
84,506 sqft / 1.94 acres (approx)
Year Built:
1970
Schools
School District:
Monomoy
Interior
Appliances
Dishwasher, Washer, Refrigerator, Microwave, Gas Water Heater
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Fireplaces Total
4
Flooring
Hardwood, Carpet, Tile, Other
Heating
Hot Water, Other
Laundry Features
Laundry Room, In Basement
Exterior
Community Features
Deeded Beach Rights
Construction Materials
Shingle Siding
Exterior Features
Garden
Parking Features
Basement
Parking Spots
6
Roof
Asphalt, Pitched, Flat
Financial
HOA Frequency
Annually
Tax Year
2025
Taxes
$5,179
Map
Contact Us
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Community
- Address55 Winterset Drive Chatham MA
- SubdivisionGreat Hills Estates
- CityChatham
- CountyBarnstable
- Zip Code02633
Subdivisions in Chatham
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Property Summary
- Located in the Great Hills Estates subdivision, 55 Winterset Drive Chatham MA is a Single Family for sale in Chatham, MA, 02633. It is listed for $2,495,000 and features 4 beds, 4 baths, and has approximately 0 square feet of living space, and was originally constructed in 1970. The average listing price for Single Family in Chatham is $2,905,129. To schedule a showing of MLS#22502257 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 Lucy55 Winterset Drive
Chatham, MA
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