Single Family Residence at 85 High St, Winchester MA 01890, Winchester
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 2 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 3 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 4 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 5 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 6 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 7 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 8 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 9 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 10 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 11 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 12 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 13 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 14 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 15 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 16 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 17 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 18 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 19 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 20 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 21 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 22 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 23 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 24 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 25 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 26 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 27 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 28 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 29 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 30 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 31 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 32 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 33 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 34 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 35 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 36 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 37 of 38
Single Family Residence at 85 High St, Winchester MA 01890, Winchester, photo 38 of 38
38 photos

$1,999,000

85 High St, Winchester MA 01890
Winchester, MA 01890
Listed by Catherine Albiani
Bedrooms
4
Bathrooms
2.5
Living area
3,757 sqft
Year built
1931

About this home

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location, ready to be loved from day one.

Highlights

Fireplace

Property details

MLS #
73565817
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
37
On market date
August 19, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
6
Lot size
0.29 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Ambrose Elementary
0.32 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
345
Student:teacher ratio
11.5:1
District
Winchester
Middle
McCall Middle
1.45 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
1.68 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Walkability

Blended score for Winchester's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

34
Car-dependent
out of 100
EPA National Walkability Index
4.8 / 20 -- Least walkable
Nearby-amenity density
48 / 100
Restaurants & cafes1
Grocery stores1
Parks8
Schools7
Transit stops20
Pharmacies0

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$12,188/mo
$399,800 down
$1,599,200 loan
Principal & interest$10,372
Property tax (est.)$1,666
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated August 25, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.