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

No listing photos
5
Beds
2.5
Baths
2,838
Sqft
1962
Year built
Range $1,461,554 – $1,669,562 · 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 $2,098,516 in July 2025; lowest $1,113,269 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$313,112
Estimated monthly payment
$10,036/mo
Loan amount $1,252,446. 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
Stratton Elementary School
KG-5 · Regular · Arlington School District
448 students · 12.2:1 student–teacher
Peirce Elementary School
KG-5 · Regular · Arlington School District
318 students · 13.2:1 student–teacher
New Covenant School
PK-5 · Regular
55 students · 7.3:1 student–teacher
Lexington Christian Academy
6-12 · Regular
281 students · 8.1:1 student–teacher
John A. Bishop Elementary School
KG-5 · Regular · Arlington School District
375 students · 12.4:1 student–teacher
Ottoson Middle School
7-8 · Regular · Arlington School District
963 students · 11.4:1 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.
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
New42$1,449,000
4 bd · 3 ba · 2,855 sqft
15 Madison Ave W, Winchester, MA
Andersen Group Realty · Keller Williams Realty Boston Northwest
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
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
Price Reduced42$1,999,000
5 bd · 4 ba · 4,063 sqft
21 Amberwood Dr, Winchester, MA
Gayle Winters & Co. Team · Compass





Within 2 miles of this home: 37+ restaurants and cafés, 4 grocery stores, 37+ parks and green spaces, and 39+ transit stops.
Place data from OpenStreetMap.
Arlington Cafe
Summer Street
Sono Asian Cuisine
Summer Street
Master Pies Pizza
Massachusetts Avenue
Dunkin
Massachusetts Avenue
Jimmy's Steer House
Massachusetts Avenue
D'Agostino's Delicatessen
Massachusetts Avenue
Classic Cafe
Massachusetts Avenue
Boston Pizza & Gyro
Massachusetts Avenue
Maruichi Japanese Food and Deli
Massachusetts Avenue
Trader Joe's
Massachusetts Avenue
Whole Foods Market
Cambridge Road
Stop & Shop
Massachusetts Avenue
Mullen Field
Rindge St Conservation
Forest St Conservation
Mount Pisgah
Smith Pond Conservation Area
Locke Farm Conservation Area
Locke Pond
Turkey Hill Reservation
Clyde Terr @ Lawrence Ln
Forest St @ Thomas St
Washington St @ Mohawk Rd
Forest St @ Hancock St
Forest St @ Heard Rd
Washington St @ Pheasant Ave
Cambridge Street @ Arlington Street
Forest St @ Sunset Rd