Price Reduced37
$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
1.5
Baths
2,813
Sqft
1999
Year built
Range $1,691,764 – $2,086,377 · 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 $1,889,071 in August 2026; lowest $809,510 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$377,814
Estimated monthly payment
$12,312/mo
Loan amount $1,511,257. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
School ratings (A+ to F) from HJN community data.
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
Chatham Elementary School
PK-4 · Regular · Monomoy Regional School District
146 students · 8.0:1 student–teacher
The Laurel School
PK-5 · Alternative/Other
38 students · 5.8:1 student–teacher
Monomoy Regional High School
8-12 · Regular · Monomoy Regional School District
738 students · 11.8:1 student–teacher
Cape Cod Region Vocational Technical
9-12 · Vocational Education · Cape Cod Regional Vocational Technical
682 students · 10.9:1 student–teacher
Harwich Elementary School
PK-4 · Regular · Monomoy Regional School District
449 students · 9.9:1 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.
Price Reduced37
$2,295,000
4 bd · 4 ba · 4,072 sqft
55 Winterset Drive, Chatham, MA
Janet Stuart · Coldwell Banker Realty - Concord
42$1,650,000
3 bd · 3 ba · 1,902 sqft
764 Riverview Drive, Chatham, MA
Dawn Boynton · 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
27$1,415,000
3 bd · 3 ba · 1,920 sqft
112 Soundview Ave, Chatham, MA
Dawn Marie Boynton · Berkshire Hathaway HomeServices Robert Paul Properties · on 2 MLSs
47$1,495,000
3 bd · 2 ba · 1,238 sqft
87 Cranberry Lane, Chatham, MA
David C Carter · Compass Massachusetts, LLC
43$1,495,000
2 bd · 2 ba · 1,810 sqft
39 Jedidiah Way, Chatham, MA
The Grattan Group · Christie's International Real Estate Atlantic Brokerage · on 2 MLSs





Within 2 miles of this home: 32 restaurants and cafés, 3 grocery stores, 32+ parks and green spaces, and 2 transit stops.
Place data from OpenStreetMap.
Hangar B Eatery
LiBAYtion
Outer Bar & Grille
The Corner Store
Twenty-Eight Atlantic
Dunkin
Route 137
400 East
Italian restaurant
Pate’s
Main Street
Stop & Shop
RPM Carpets & Floor Coverings
Long Pond Road
Chatham Village Market
Orleans Road
Muddy Creek Pleasant Bay Est Es
Pinkwink Pond
Muddy Creek
Trout Pond
Stillwater Pond
Muddy Creek South
Roberts Gift
Stop & Shop - East Harwich
Chatham - Anchorage/Crowell Rd