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
5
Beds
4
Baths
5,083
Sqft
1915
Year built
Range $2,261,385 – $2,457,225 · as of August 30, 2026
ATTOM automated valuation model · 54 published estimates over 6.7 years · shaded band is the model's own published low-to-high range
Highest reading $3,027,015 in May 2025; lowest $1,673,417 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$471,861
Estimated monthly payment
$15,348/mo
Loan amount $1,887,444. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
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.
School ratings (A+ to F) from HJN community data.
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
McCall Middle School
6-8 · Regular · Winchester School District
1,036 students · 12.6:1 student–teacher
Lincoln Elementary School
KG-5 · Regular · Winchester School District
334 students · 11.1:1 student–teacher
Medford High School
9-12 · Regular · Medford School District
1,195 students · 9.2:1 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
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 student–teacher
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
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
New40$2,199,000
6 bd · 5 ba · 4,947 sqft
42 Everett Ave, Winchester, MA
The Pallotta Group · Gibson Sotheby's International Realty
New42$2,049,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass
Price Reduced42$1,999,000
4 bd · 4 ba · 3,640 sqft
7 Wainwright Road #113, Winchester, MA
Kim Covino & Co. Team · Compass
39$2,399,000
4 bd · 4 ba · 3,550 sqft
63 Wedgemere Avenue, Winchester, MA
Paula R. Sughrue · Better Homes and Gardens Real Estate - The Shanahan Group





Within 2 miles of this home: 39+ restaurants and cafés, 2 grocery stores, 38+ parks and green spaces, and 33+ transit stops.
Place data from OpenStreetMap.
Black Horse Tavern
Waterfield Road
A Tavola
Italian restaurant · Church Street
Nouvelle Maison Fine Provisions
D'Agostino's Delicatessen
First House Pub
Frozen Hoagies
Main Street
Nourish Your Soul
Starbucks
Main Street
Stop & Shop
Main Street
Whole Foods Market
Mystic Valley Parkway
Brooks Parkhurst Town Forest
Ginn Field
Stone Family Playground
Shannon Beach
Brooks Estate
Brooks Pond
Dennett Park
Mystic Valley Parkway
Main Street @ Ridgefield Road
Main Street @ Everell Road
Main Street @ Highland Avenue
Main Street @ Marshall Road
Main Street opposite Highland Avenue
Main Street @ Madison Avenue West
Main Street @ Gateway South
Wedgemere