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
Baths
2,810
Sqft
1955
Year built
Range $1,541,035 – $1,995,157 · 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 $1,768,096 in October 2026; lowest $817,149 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$353,619
Estimated monthly payment
$11,320/mo
Loan amount $1,414,477. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
Acera School
KG-10 · Special Program Emphasis
144 students · 4.0:1 student–teacher
Muraco Elementary School
KG-5 · Regular · Winchester School District
352 students · 10.9:1 student–teacher
Goodyear Elementary School
KG-5 · Regular · Woburn School District
352 students · 11.1:1 student–teacher
South Elementary School
PK-4 · Regular · Stoneham School District
347 students · 12.3:1 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
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
Shamrock Elementary School
KG-5 · Regular · Woburn School District
284 students · 10.4:1 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
New42$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 Reduced40$2,149,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
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





Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Winchester camera map3 license-plate readers mapped within 1 mile of this home, all identified as Flock Safety devices. None within ½ mile. Nearest: 0.7 mi north. Operator named in the data: Woburn Police.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| License-plate readers | 0 | 3 |
| of which Flock Safety | 0 | 3 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
License-plate readers (ALPR) are fixed cameras that photograph passing vehicles and read their plates. Records are typically shared with the agency or association that operates the camera.
Flock Safety is a company whose plate-reader cameras are used by police departments, cities, HOAs and businesses. Its devices are usually solar-powered and pole-mounted.
Within 2 miles of this home: 36+ restaurants and cafés, 3 grocery stores, 36+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Eighty Eight Cafe
Chinese restaurant · Washington Street
Wendy's
Montvale Avenue
Polcari's Restaurant
Italian restaurant · Montvale Avenue
Bickford's Grille
Montvale Avenue
McDonald's
Montvale Avenue
Dunkin
Montvale Avenue
Sam Walker’s American Tavern
Rainin Road
Swanton Street Diner
Swanton Street
Stop & Shop
Main Street
Natural Food Exchange
Pleasant Street
Apna Bazar
Davidson Park
Leonard Field
Aberjona River
Leland Park
Dikes Pond
Middlesex Fells Reservation
North Reservoir
Conservation Land/Meadow Road
Montvale Ave @ Washington St
Montvale Ave @ I93 ramp
Montvale Ave @ I93
42 Central St
Central St @ Montvale Ave
Central St @ Washington Circle
Central St @ Pine Street
Main St @ Graystone Rd