55 Winterset Drive
Chatham, MA, 02633
$2,390,000
Spectacular four bedroom home set on one of the largest lots in sought-after Great Hill Estates. With deeded rights to Lover’s Lake for swimming, kayaking & fishing just a short path away. Located at the end of a quiet cul-de-sac, this home offers true privacy & 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. Possible subdivision opportunity.
Current real estate data for Single Family in Chatham as of Jul 26, 2026
58
Single Family Listed
101
Avg DOM
1,009
Avg $ / SqFt
$2,873,457
Avg List Price
Property Details
Price:
$2,390,000
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
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, Eat-in Kitchen, Kitchen Island, Breakfast Bar
Laundry Features
Laundry Room
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
Map
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Community
- Address55 Winterset Drive Chatham MA
- SubdivisionGreat Hills
- CityChatham
- CountyBarnstable
- Zip Code02633
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 $2,390,000 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 $588. The average price per square foot for Single Family listings in Chatham is $1,009. The average listing price for Single Family in Chatham is $2,873,457. 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…
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55 Winterset Drive
Chatham, MA