Price Reduced42
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord

No listing photos
3
Beds
3.5
Baths
1,863
Sqft
2016
Year built
Range $2,141,981 – $2,584,131 · as of August 30, 2026
ATTOM automated valuation model · 55 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $2,995,000 in July 2024; lowest $1,071,468 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$472,611
Estimated monthly payment
$15,372/mo
Loan amount $1,890,445. 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
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.
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: 0.9 mi north.
| 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.
Price Reduced42
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord
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
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
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
Price Reduced44$1,695,000
2 bd · 4 ba · 2,331 sqft
43 Tobey Turtle Road, Chatham, MA
Timothy P Bailey · John C Ricotta & Assoc.





Within 2 miles of this home: 33 restaurants and cafés, 1 grocery store, 32+ parks and green spaces, and 2 transit stops.
Place data from OpenStreetMap.
Cuvée
Chatham Village Cafe
Chatham Perk
Buffy's Ice Cream
Main Street
Aplaya Kitchen and Tiki Bar
Main Street
Snowy Owl Coffee
The Chatham Squire
Main Street
Impudent Oyster
Chatham Bars Avenue
Chatham Village Market
Lighthouse Beach
Bridge Street Lot 10
Ive Parcel
Off Morris Island Road
Morris Island Road / Bridge St
28 Bridge Street
Ivy Lane
Lighthouse Park
Main Street
Chatham - Rotary
Chatham - Anchorage/Crowell Rd