Price Reduced40
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord · on 2 MLSs

No listing photos
3
Beds
5
Baths
2,476
Sqft
2005
Year built
Range $2,562,567 – $2,995,013 · as of August 30, 2026
ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $2,929,840 in January 2026; lowest $1,011,173 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$555,758
Estimated monthly payment
$17,935/mo
Loan amount $2,223,032. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
School ratings (A+ to F) from HJN community data.
Chatham Elementary School
PK-4 · Regular · Monomoy Regional School District
146 students · 8.0:1 student–teacher
Monomoy Regional Middle School
5-7 · Regular · Monomoy Regional School District
395 students · 9.8:1 student–teacher
Cape Cod Lighthouse Charter School
6-8 · Regular · Cape Cod Lighthouse Charter
251 students · 11.8:1 student–teacher
Within 2 miles of this home: 39+ restaurants and cafés, 1 grocery store, 30+ parks and green spaces, and 2 transit stops.
Place data from OpenStreetMap.
Branches
Pain D’Avion
Sweet Tomatoes Neopolitan Pizza
Main Street
Chatham Fish & Chips
Chatham Filling Station
Red Nun Bar & Grill
Main Street
Codo Mexican Kitchen
Mexican restaurant
Three Fins Coffee Roasting
Crowell Road
Chatham Village Market
Conservation Land
Veterans' Park
Off Old Harbor Road / Patten Lane Parcel
Oyster Pond Furlong
Main Street Route 28
Nickerson Park
Queen Anne Road / Oyster Pond
Route 28 Main Street
Chatham - Anchorage/Crowell Rd
Chatham - Rotary
Cape Cod & Islands Association of REALTORS
MLS Property Information Network (MLS PIN)Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Price Reduced40
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord · on 2 MLSs
72$2,199,000
3 bd · 3 ba · 2,848 sqft
312 Round Cove Road, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties · on 2 MLSs
48$2,199,900
3 bd · 3 ba · 2,576 sqft
20 Lords Pond Road, Chatham, MA
The Grattan Group · Christie's International Real Estate Atlantic Brokerage
Price Reduced78$2,699,000
3 bd · 3 ba · 2,205 sqft
336 Stage Island Road, Chatham, MA
Guthrie Schofield Group · Berkshire Hathaway HomeServices Robert Paul Properties · on 2 MLSs

$3,299,900
3 bd · 4 ba · 3,157 sqft
9 Bassing Harbor Road, Chatham, MA
The Grattan Group · Christie's International Real Estate Atlantic Brokerage
42$2,199,900
3 bd · 4 ba · 2,576 sqft
20 Lords Pond Lane, Chatham, MA
Andrew Grattan · Christie's International Real Estate Atlantic Brokerage





Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Chatham camera map1 CCTV camera mapped within 1 mile of this home. None within ½ mile. Nearest: 0.7 mi southeast.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| CCTV cameras | 0 | 1 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
CCTV cameras are fixed video cameras that record a street, building or other area.