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
4
Beds
3.5
Baths
4,768
Sqft
1925
Year built
Range $2,210,161 – $2,453,637 · 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 $2,398,268 in June 2025; lowest $1,496,003 in February 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$466,380
Estimated monthly payment
$14,892/mo
Loan amount $1,865,519. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
Van - Owen Elementary School
KG-5 · Regular · Winchester School District
441 students · 12.5:1 student–teacher
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
Lexington Christian Academy
6-12 · Regular
281 students · 8.1:1 student–teacher
Peirce Elementary School
KG-5 · Regular · Arlington School District
318 students · 13.2:1 student–teacher
Harrington Elementary School
KG-5 · Regular · Lexington School District
374 students · 10.0:1 student–teacher
Stratton Elementary School
KG-5 · Regular · Arlington School District
448 students · 12.2:1 student–teacher
Reeves Elementary School
KG-5 · Regular · Woburn School District
451 students · 13.7:1 student–teacher
New Covenant School
PK-5 · Regular
55 students · 7.3:1 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 Reduced41$1,744,000
3 bd · 4 ba · 3,010 sqft
1 Town Way, 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





Within 2 miles of this home: 37+ restaurants and cafés, 3 grocery stores, 37+ parks and green spaces, and 38+ transit stops.
Place data from OpenStreetMap.
Dunkin
Cambridge Road
Krave Kitchen & Bar
American restaurant · Cambridge Road
Sogno
Italian restaurant · Cambridge Road
Lexington House of Pizza
Arlington Cafe
Summer Street
Sono Asian Cuisine
Summer Street
McDonald's
Cambridge Road
Ninety Nine Restaurant & Pub
American restaurant · Cambridge Road
Whole Foods Market
Cambridge Road
Maruichi Japanese Food and Deli
Massachusetts Avenue
Trader Joe's
Massachusetts Avenue
Smith Pond Conservation Area
Sachem Swamp Conservation Area
Locke Farm Conservation Area
Mullen Field
Vernal Pool
Locke Pond
Mount Pisgah
Winning Farm Conservation Area
Winchester Drive @ Russell Road
Winchester Drive opposite Tyler Road
Russell Road @ Whipple Road
Whipple Road @ Fiske Road
Clyde Terr @ Lawrence Ln
Forest St @ Thomas St
Whipple Road @ Locke Lane
Winchester Drive @ Fiske Road