Single Family Residence at 85 High Street, Winchester
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$1,899,000

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

About this home

Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare 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
MLS Property Information Network
MLS #
73596915
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
4
On market date
October 30, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
6
Lot size
0.29 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

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, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 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
Google Places amenity density
48 / 100
Restaurants & cafes1
Grocery stores1
Parks8
Schools7
Transit stops20
Pharmacies0

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 4 days -- 88 fewer days than Winchester's current average of 92 days.
For reference, the median list price across 175 active listings in Winchester right now is $799,000.

Mortgage calculator

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

Adjust tax / insurance estimates
Est. monthly payment
$11,586/mo
$379,800 down
$1,519,200 loan
Principal & interest$9,854
Property tax (est.)$1,583
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated 2 days ago.

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.