Price Reduced38
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord

No listing photos
5
Beds
3
Baths
2,472
Sqft
1860
Year built
Range $2,514,491 – $3,133,237 · 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 $3,197,385 in October 2024; lowest $1,523,064 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$564,773
Estimated monthly payment
$18,347/mo
Loan amount $2,259,091. 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
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: 0.7 mi northeast.
| 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.
Within 2 miles of this home: 40+ restaurants and cafés, 1 grocery store, 28+ parks and green spaces, and 2 transit stops.
Place data from OpenStreetMap.
Emack & Bolio's
Aplaya Kitchen and Tiki Bar
Main Street
The Chatham Squire
Main Street
Snowy Owl Coffee
Bluefins Sushi and Sake Bar
Viera On Main
Chatham Cookware
Wild Goose Tavern
Chatham Village Market
Stage Harbor Road
Cedar Street
Honeysuckle Lane
Lot 2 Off Elizabaths Way
Crocker Rise Ii
Snug Harbor Road / Mill Pond
Crocker Rise I
Hardings Lane
Chatham - Rotary
Chatham - Anchorage/Crowell Rd