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
4
Beds
3.5
Baths
2,807
Sqft
1980
Year built
Range $1,546,794 – $2,565,410 · as of July 14, 2026
ATTOM automated valuation model · 53 published estimates over 6.5 years · shaded band is the model's own published low-to-high range
Highest reading $2,090,357 in June 2025; lowest $1,196,280 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$411,220
Estimated monthly payment
$13,390/mo
Loan amount $1,644,882. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 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
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 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
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 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
Joyce Middle School
6-8 · Regular · Woburn School District
455 students · 8.3:1 student–teacher
Within 2 miles of this home: 37+ restaurants and cafés, 2 grocery stores, 36+ parks and green spaces, and 37+ 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
Meet Us
Asian restaurant
Boston King Coffee
Cambridge Road
Taco Bell
Cambridge Road
Whole Foods Market
Cambridge Road
Stop & Shop
Main Street
The Gables Cr
West Side Field
Sucker Brook Conservation Area
Loves Lane Conservation Area
Woburn Reservoir (Historic)
Winter Pond
Sachem Swamp Conservation Area
Mount Pisgah
Cambridge Street opposite Pond Street
Cambridge Street @ Pond Street
Cambridge Road @ New England Rehab Hospital
Cambridge Road @ Crescent Park Drive
Cambridge Road @ Country Club Road
Cambridge Street @ Wildwood Street
259 Cambridge Road
254 Cambridge Road
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
Price Reduced41$2,195,000
5 bd · 4 ba · 5,006 sqft
276 High Street, Winchester, MA
Kim Covino & Co. Team · Compass
New42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
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
Price Reduced42$1,999,000
4 bd · 4 ba · 3,640 sqft
7 Wainwright Road #113, Winchester, MA
Kim Covino & Co. Team · Compass




