41
$1,850,000
4 bd · 3 ba · 3,092 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
3,831
Sqft
2004
Year built
Range $1,680,105 – $1,771,483 · 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 $1,893,481 in April 2026; lowest $1,210,377 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$345,159
Estimated monthly payment
$11,145/mo
Loan amount $1,380,635. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 38+ restaurants and cafés, 2 grocery stores, 35+ parks and green spaces, and 34+ transit stops.
Place data from OpenStreetMap.
Arancini Italian Restaurant
Italian restaurant · Main Street
Gloria's Pizzeria
Main Street
Sakura Japanese
Japanese restaurant · Main Street
Andrea's Pizza
Main Street
Dunkin
Main Street
Mitho Restaurant
Main Street
Louie's Pizza
Main Street
Burger King
Main Street
Stop & Shop
Main Street
Whole Foods Market
Cambridge Road
McDonald Field
Horn Pond Brook
Bellino Park
Well Field
Flemming Field
Middlesex Park
Clapp Park
Horn Pond
Main Street opposite Sheridan Circle
Main Street @ Sheridan Circle
Main Street @ Hemingway Street
Main St @ Lydon Ct
Main Street opposite Hemingway Street
Main St @ Cranes Ct
Main Street @ Canal Street
96 Main St
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 · 3,092 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
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
Price Reduced38$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High St, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group
Price Reduced42$1,999,000
4 bd · 4 ba · 3,640 sqft
7 Wainwright Road #113, Winchester, MA
Kim Covino & Co. Team · Compass





School ratings (A+ to F) from HJN community data.
Lynch Elementary School
KG-5 · Regular · Winchester School District
426 students · 10.8:1 student–teacher
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
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Shamrock Elementary School
KG-5 · Regular · Woburn School District
284 students · 10.4:1 student–teacher
St Charles School
PK-8 · Regular
162 students · 12.1:1 student–teacher
St Mary's School
PK-KG · Early Childhood Program/Child Care Center
9 students · 9.0:1 student–teacher
The Wilder School
UG-UG · Alternative/Other
2 students · 1.8:1 student–teacher