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
2.5
Baths
2,548
Sqft
1961
Year built
Range $1,426,174 – $1,510,661 · 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 $1,739,628 in June 2024; lowest $976,411 in January 2024. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$293,683
Estimated monthly payment
$9,421/mo
Loan amount $1,174,734. 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
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Brooks Elementary School
PK-5 · Regular · Medford School District
556 students · 12.6:1 student–teacher
St Raphael School
PK-8 · Regular
255 students · 13.9:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 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
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
42$1,449,000
4 bd · 3 ba · 2,855 sqft
15 Madison Ave W, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest
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
Price Reduced40$1,049,000
4 bd · 3 ba · 2,411 sqft
24 Richardson St, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest





Within 2 miles of this home: 39+ restaurants and cafés, 3 grocery stores, 38+ parks and green spaces, and 36+ transit stops.
Place data from OpenStreetMap.
Magnificent Muffin and Bagel Shoppe
Amore Pizza & Kitchen
C.B. Scoops
Hong Kong Village
Chinese restaurant
Amici's
Italian restaurant
Paul Revere Restaurant
El Vaquero
Mexican restaurant
Lucy's
Whole Foods Market
Mystic Valley Parkway
Stop & Shop
Main Street
Ebisuya Japanese Market
Riverside Avenue
Dennett Park
Brooks Parkhurst Town Forest
Brooks Pond
Brooks Estate
Honor Roll Park
Victory Park
Mystic Lakes State Park
Hastings Heights Park
713 Winthrop St opp Robinson Rd
Winthrop St @ Robinson Rd
Main Street @ Town Way
Winthrop St @ Winford Way
Winthrop St opp Winford Way
Main Street @ Gateway South
Main Street opposite Highland Avenue
Playstead Rd @ Winthrop St - W Medford Sq