40
$1,850,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group

No listing photos
4
Beds
2.5
Baths
2,514
Sqft
1925
Year built
Range $1,545,542 – $1,665,628 · 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 $1,605,585 in August 2026; lowest $983,381 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$321,117
Estimated monthly payment
$10,482/mo
Loan amount $1,284,468. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 39+ restaurants and cafés, 3 grocery stores, 38+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Black Horse Tavern
Waterfield Road
First House Pub
Frozen Hoagies
Main Street
Comella's
D'Agostino's Delicatessen
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
Starbucks
Main Street
Stop & Shop
Main Street
Whole Foods Market
Mystic Valley Parkway
Ebisuya Japanese Market
Riverside Avenue
Brooks Parkhurst Town Forest
Dennett Park
Ginn Field
Stone Family Playground
Brooks Pond
Brooks Estate
Mystic Valley Parkway
Manchester Field
Main Street @ Highland Avenue
Main Street opposite Highland Avenue
Main Street @ Gateway South
Main Street @ Everell Road
Main Street @ Town Way
Main Street @ Ridgefield Road
Main Street @ Marshall Road
Main Street @ Madison Avenue West
School ratings (A+ to F) from HJN community data.
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 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.
40
$1,850,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
Price Reduced42$1,649,000
3 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
Price Reduced41$1,749,000
3 bd · 4 ba · 3,010 sqft
1 Town Way, Winchester, MA
Vita Realty Group · Compass
38$1,299,000
3 bd · 2 ba · 2,350 sqft
39 Forest St, Winchester, MA
Danielle Storella · Berkshire Hathaway HomeServices Commonwealth Real Estate
32$1,529,000
4 bd · 4 ba · 2,709 sqft
25 Arlington St, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington




