Price Reduced40
$1,650,000
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
5
Beds
3.5
Baths
4,204
Sqft
1900
Year built
Range $2,044,049 – $2,277,269 · as of October 21, 2026
ATTOM automated valuation model · 55 published estimates over 6.8 years · shaded band is the model's own published low-to-high range
Highest reading $3,338,336 in June 2024; lowest $1,317,097 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$432,132
Estimated monthly payment
$13,807/mo
Loan amount $1,728,527. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
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
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 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.
Price Reduced40
$1,650,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
42$1,650,000
5 bd · 4 ba · 3,722 sqft
117 Highland, Winchester, MA
Dara Singleton · Better Homes and Gardens Real Estate - The Shanahan Group
37$1,749,000
5 bd · 4 ba · 3,508 sqft
17 Churchill Rd, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington
Price Reduced40$2,149,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
Price Reduced30$2,750,000
6 bd · 7 ba · 6,968 sqft
14 Nassau Drive, Winchester, MA
Weidong Li · WINN Real Estate & Consulting
Price Reduced36$1,749,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group





Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 37+ parks and green spaces, and 32+ transit stops.
Place data from OpenStreetMap.
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
Black Horse Tavern
Waterfield Road
D'Agostino's Delicatessen
First House Pub
Nourish Your Soul
Frozen Hoagies
Main Street
The Bagel Bar
Stop & Shop
Main Street
Whole Foods Market
Cambridge Road
Ginn Field
Stone Family Playground
Brooks Parkhurst Town Forest
Shannon Beach
Mystic Valley Parkway
Manchester Field
Glen Green
Town Common
Wedgemere
Main Street @ Ridgefield Road
Main Street @ Everell Road
Main Street @ Marshall Road
Main Street @ Madison Avenue West
Main Street @ Lincolnshire Way
Main Street @ Chestnut Street
Main Street @ Mystic Avenue