Single Family Residence at 276 High Street, Winchester MA 01890
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$2,195,000

276 High Street, Winchester MA 01890
Winchester, MA 01890
Listed by Kim Covino & Co. Team
Bedrooms
5
Bathrooms
3.5
Living area
5,006 sqft
Year built
1992

About this home

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73496396
Property type
Single Family Residence
Subdivision
Cox Road / High St Extension neighborhood
Status
Active
Days on market
201
On market date
April 6, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
3
Parking spaces
9
Lot size
0.46 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
Vinson-Owen Elementary
0.57 mi away · Grades -1-5
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
411
Student:teacher ratio
12.5:1
District
Winchester
Middle
Ottoson Middle
1.55 mi away · Grades 7-8
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
906
Student:teacher ratio
11.3:1
District
Arlington
High
Arlington High
2.01 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
1,483
Student:teacher ratio
13.0:1
District
Arlington

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).

46
Somewhat walkable
out of 100
EPA National Walkability Index
9.7 / 20 -- Below average walkable
Google Places amenity density
43 / 100
Restaurants & cafes1
Grocery stores0
Parks9
Schools9
Transit stops14
Pharmacies0

Market position

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

On the market 201 days -- 118 more days than Winchester's current average of 83 days.
For reference, the median list price across 179 active listings in Winchester right now is $850,000.

Mortgage calculator

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

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Est. monthly payment
$13,369/mo
$439,000 down
$1,756,000 loan
Principal & interest$11,389
Property tax (est.)$1,829
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 16 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.