Sold Jun 23, 2026$2,350,000
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Active
55 Winterset Drive
Chatham, MA 02633
Offered at$2,390,000
Residential · Active · MLS #73548377
Listing Courtesy of Coldwell Banker Realty - Concord | Janet Stuart
4Bedrooms
4Bathrooms
4,072Square feet
1970Year built
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MLS PIN data
About this home
Spectacular four bedroom home set on almost two acres in sought-after Great Hill. Enjoy breezy nights and summer days with deeded rights to 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, four fireplaces, open floor plan and wraparound decks with elevated views of the expansive property, all perfect for entertaining and large family gatherings. The first floor has two large great rooms with soaring beamed ceilings and floor-to-ceiling fireplaces, a large kitchen with granite and island with seating open to a dining area, a primary suite with en-suite full bathroom with washer dryer and lots of closets, and a half bath. Upstairs is a second primary bedroom with walk-in closet, its own fireplace and sitting area, an additional bedroom, and a full bath. The walkout lower level has a bedroom with full windows, a full bath, and another washer/dryer which all leads to a stone patio with fire pit and custom built stone seating.. Close to Chatham Village, bike bath and Chatham beaches.
Property information
Details at a glance
Interior
- Rooms
- 8
- Heating
- Baseboard, Natural Gas
- Cooling
- Central Air, Ductless
- Flooring
- Tile, Carpet, Hardwood
- Fireplaces
- 4
Building
- Style
- Single Family Residence
- Year built
- 1970
- Garage
- 2
- Parking
- 14
- Foundation
- Concrete Perimeter
- Roof
- Shingle
Land & utilities
- Lot size
- 1.94 acres
- Water
- Public
- Sewer
- Private Sewer
- Zoning
- res
Financial
- Annual taxes
- $5,655
- Assessment year
- 2026
- HOA fee
- 75
Listing history
Price and status timeline
No additional public listing history was supplied for this property.
Property value estimate
An informed starting point
Automated estimates are not appraisals or guarantees of market value.
Comparable sales
Recent properties for context
Sold Jul 8, 2026$2,250,000
23 Stony Brook Rd
Photo insights
Condition signals
Overall presentationabove average
Generated from listing photography; not a substitute for an inspection.
Local market context
How this home compares in Chatham
MetricThis propertyChatham
List price$2,390,000$2,850,00016% below local
Price / sq ft$587$1,14549% below local
Days on market549141% below local
Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.
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Common questions
About 55 Winterset Drive
Can I schedule a private showing?
Yes. Request a tour of 55 Winterset Drive and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.