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
4,839
Sqft
1989
Year built
Range $2,098,175 – $2,324,371 · 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 $2,420,000 in September 2023; lowest $1,590,532 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$442,255
Estimated monthly payment
$14,044/mo
Loan amount $1,769,018. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
Muraco Elementary School
KG-5 · Regular · Winchester School District
352 students · 10.9:1 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
Acera School
KG-10 · Special Program Emphasis
144 students · 4.0:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Greater Boston Academy
PK-8 · Regular
136 students · 21.6:1 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
Price Reduced42$2,250,000
6 bd · 4 ba · 3,534 sqft
7 Lakeview Terrace, Winchester, MA
Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate
Price Reduced42$1,999,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
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





Within 2 miles of this home: 37+ restaurants and cafés, 2 grocery stores, 37+ parks and green spaces, and 32+ transit stops.
Place data from OpenStreetMap.
Eighty Eight Cafe
Chinese restaurant · Washington Street
Swanton Street Diner
Swanton Street
Domino's
Main Street
China Sky
Converse Place
Lucia's Ristorante & Bar
Italian restaurant
Eleni's Mediterranean Grille
Toscano's Italian Kitchen
Main Street
Caffè Nero
Stop & Shop
Main Street
Natural Food Exchange
Pleasant Street
Middlesex Fells Reservation
Long Pond
Middle Reservoir
North Reservoir
Highland Park
Leonard Field
Aberjona River
Sheepfold
Main St @ Lake St
Main St @ Vine St
757 Main Street
Winchester Center
Main Street @ Fairview Terrace
Main Street @ Washington Street
Main Street @ Clark Street
Main Street opposite Richardson Street