Price Reduced40
$1,750,000
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
3
Beds
2.5
Baths
2,488
Sqft
1940
Year built
Range $1,326,240 – $1,400,146 · as of August 30, 2026
ATTOM automated valuation model · 55 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $1,536,415 in June 2025; lowest $866,243 in January 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$272,639
Estimated monthly payment
$8,798/mo
Loan amount $1,090,554. 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
Acera School
KG-10 · Special Program Emphasis
144 students · 4.0:1 student–teacher
Goodyear Elementary School
KG-5 · Regular · Woburn School District
352 students · 11.1:1 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
South Elementary School
PK-4 · Regular · Stoneham School District
347 students · 12.3:1 student–teacher
Shamrock Elementary School
KG-5 · Regular · Woburn School District
284 students · 10.4:1 student–teacher
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: 0.9 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, 2 grocery stores, 36+ parks and green spaces, and 31+ transit stops.
Place data from OpenStreetMap.
Eighty Eight Cafe
Chinese restaurant · Washington Street
Swanton Street Diner
Swanton 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
Stop & Shop
Main Street
Natural Food Exchange
Pleasant Street
Davidson Park
Leonard Field
Aberjona River
Leland Park
Middlesex Fells Reservation
Long Pond
North Reservoir
Dikes Pond
Montvale Ave @ Washington St
Montvale Ave @ I93 ramp
Montvale Ave @ I93
42 Central St
Central St @ Montvale Ave
Main Street opposite Richardson Street
Main Street @ Clark Street
757 Main Street
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
$1,750,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
41$1,049,900
3 bd · 2 ba · 1,783 sqft
28 Olive St, Winchester, MA
Ethan Forrest · The Aland Realty Group LLC
New42$1,699,000
4 bd · 3 ba · 2,736 sqft
3 Sunset Road, Winchester, MA
Kim Covino & Co. Team · Compass
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
Price Reduced28$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
Price Reduced28$1,250,000
4 bd · 3 ba · 2,666 sqft
465 Washington Street #465, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty




