36
$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group

No listing photos
5
Beds
4.5
Baths
3,778
Sqft
1910
Year built
Range $1,759,386 – $1,954,310 · 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 $2,456,750 in March 2026; lowest $1,210,666 in April 2020. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.
$371,370
Estimated monthly payment
$11,942/mo
Loan amount $1,485,478. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
School ratings (A+ to F) from HJN community data.
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
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
Winchester High School
9-12 · Regular · Winchester School District
1,404 students · 14.8:1 student–teacher
Childrens Own School
PK-PK · Montessori
15 students · 3.0:1 student–teacher
Muraco Elementary School
KG-5 · Regular · Winchester School District
352 students · 10.9:1 student–teacher
Ambrose Elementary School
KG-5 · Regular · Winchester School District
398 students · 12.1:1 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.
36
$1,899,000
4 bd · 3 ba · 3,757 sqft
85 High Street, Winchester, MA
Catherine Albiani · Better Homes and Gardens Real Estate - The Shanahan Group
42$1,699,000
4 bd · 3 ba · 2,736 sqft
3 Sunset Road, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced42$1,499,000
4 bd · 2 ba · 2,421 sqft
4 Churchill Road, Winchester, MA
Kim Covino & Co. Team · Compass
Price Reduced40$2,149,000
4 bd · 4 ba · 3,570 sqft
19 Hancock Street, Winchester, MA
Vita Realty Group · Compass
Price Reduced42$2,299,000
4 bd · 5 ba · 4,450 sqft
54 Squire Road, Winchester, MA
Anthony Marino · The Marino Group Collection
Price Reduced41$2,195,000
5 bd · 4 ba · 5,006 sqft
276 High Street, Winchester, MA
Kim Covino & Co. Team · Compass





Within 2 miles of this home: 38+ restaurants and cafés, 2 grocery stores, 36+ parks and green spaces, and 32+ transit stops.
Place data from OpenStreetMap.
Black Horse Tavern
Waterfield Road
First House Pub
Frozen Hoagies
Main Street
D'Agostino's Delicatessen
Comella's
Starbucks
Main Street
Nourish Your Soul
A Tavola
Italian restaurant · Church Street
Stop & Shop
Main Street
Whole Foods Market
Cambridge Road
Manchester Field
Mystic Valley Parkway
Stone Family Playground
Mill Pond
Ginn Field
Town Common
Chefalo Park
Judkins Pond
Main Street @ Prospect Street
Main Street @ Mystic Avenue
Main Street @ Washington Street
Main Street @ Fairview Terrace
Main Street @ Lincolnshire Way
Main Street @ Chestnut Street
Winchester Center
Main Street @ Madison Avenue West