41
$1,850,000
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
2,205
Sqft
1955
Year built
Range $1,404,472 – $1,530,872 · as of July 14, 2026
ATTOM automated valuation model · 54 published estimates over 6.5 years · shaded band is the model's own published low-to-high range
Highest reading $1,579,467 in July 2025; lowest $739,771 in January 2024. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$293,534
Estimated monthly payment
$9,496/mo
Loan amount $1,174,138. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 37+ restaurants and cafés, 4 grocery stores, 36+ 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
Ninety Nine Restaurant & Pub
American restaurant · Cambridge Road
McDonald's
Cambridge Road
Boston King Coffee
Cambridge Road
Meet Us
Asian restaurant
Taco Bell
Cambridge Road
Whole Foods Market
Cambridge Road
Stop & Shop
Main Street
Maruichi Japanese Food and Deli
Massachusetts Avenue
Trader Joe's
Massachusetts Avenue
Sachem Swamp Conservation Area
Sucker Brook Conservation Area
Mount Pisgah
Smith Pond Conservation Area
West Side Field
Loves Lane Conservation Area
Mullen Field
The Gables Cr
Cambridge Street opposite Pond Street
Cambridge Street @ Pond Street
Cambridge Street @ Wildwood Street
Cambridge Street @ Blossom Hill Road
Cambridge Road @ New England Rehab Hospital
Cambridge Street @ Foxcroft Road
Cambridge Road @ Crescent Park Drive
Cambridge Road @ Country Club Road
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
Reeves Elementary School
KG-5 · Regular · Woburn School District
451 students · 13.7:1 student–teacher
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
Stratton Elementary School
KG-5 · Regular · Arlington School District
448 students · 12.2:1 student–teacher
Harrington Elementary School
KG-5 · Regular · Lexington School District
374 students · 10.0:1 student–teacher
Peirce Elementary School
KG-5 · Regular · Arlington School District
318 students · 13.2:1 student–teacher
Lexington Christian Academy
6-12 · Regular
281 students · 8.1:1 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.
41
$1,850,000
4 bd · 3 ba · 3,604 sqft
1 Overlook Way, Winchester, MA
Lynne Russo · Better Homes and Gardens Real Estate - The Shanahan Group
42$1,495,000
4 bd · 3 ba · 2,973 sqft
7 Sherman Place #7, Winchester, MA
John Dean · Engel & Volkers Boston
Price Reduced41$1,749,000
3 bd · 4 ba · 3,010 sqft
1 Town Way, Winchester, MA
Vita Realty Group · Compass
38$1,195,000
3 bd · 2 ba · 2,239 sqft
4 Stone Ave, Winchester, MA
The Synergy Group · The Synergy Group
Price Reduced42$1,649,000
3 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
32$1,529,000
4 bd · 4 ba · 2,709 sqft
25 Arlington St, Winchester, MA
Domingo Medina · Coldwell Banker Realty - Lexington




