Price Reduced41$1,549,000
5 bd · 3 ba · 4,208 sqft
20 Winter Street, Medfield, MA

No listing photos
5
Beds
4.5
Baths
4,004
Sqft
2005
Year built
Range $1,948,283 – $2,160,817 · 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 $2,164,484 in September 2025; lowest $1,213,857 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$410,910
Estimated monthly payment
$13,380/mo
Loan amount $1,643,640. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
School ratings (A+ to F) from HJN community data.
Thomas Blake Middle School
6-8 · Regular · Medfield School District
574 students · 10.9:1 student–teacher
Medfield Senior High School
9-12 · Regular · Medfield School District
704 students · 12.7:1 student–teacher
Montrose School
6-12 · Regular
199 students · 7.5:1 student–teacher
Memorial School
PK-1 · Regular · Medfield School District
412 students · 18.6:1 student–teacher
Dale Street
4-5 · Regular · Medfield School District
384 students · 13.3:1 student–teacher
Ralph Wheelock School
2-3 · Regular · Medfield School District
404 students · 18.1:1 student–teacher
Dover-Sherborn Middle School
6-8 · Regular · Dover-Sherborn School District
471 students · 9.5:1 student–teacher
Dover-Sherborn High School
9-12 · Regular · Dover-Sherborn School District
610 students · 9.8:1 student–teacher
Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Gail LiDonni · Legacy Properties

MLS Property Information Network (MLS PIN)Within 2 miles of this home: 9 restaurants and cafés, 2 grocery stores, and 32+ parks and green spaces.
Place data from OpenStreetMap.
Blue Moon Bagel Cafe
Takara's
Asian restaurant
Starbucks
Main Street
Zebra's Bistro Restaurant
American restaurant
Go Fresh
China Sky
North Street
Noon Hill Grill
Dunkin
Main Street
Shaw's
Brothers Marketplace
Main Street
Pinecroft Farm
Hawthorne Village Conservation Area
June Pond
Fork Factory Brook
Rocky Woods Reservation
Echo Lake
Conservation Restriction
Notch Pond