276 High Street
Winchester, MA, 01890
$2,299,000
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!
Current real estate data for Single Family in Winchester as of Oct 07, 2025
62
Single Family Listed
65
Avg DOM
551
Avg $ / SqFt
$2,270,911
Avg List Price
Property Details
Price:
$2,299,000
MLS #:
73404344
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Cox Road / High St Extension neighborhood
Listed Date:
Jul 14, 2025
Finished Sq Ft:
5,006
Total Sq Ft:
5,006
Lot Size:
19,998 sqft / 0.46 acres (approx)
Year Built:
1992
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Whs
Interior
Appliances
Water Heater, Range, Oven, Dishwasher, Disposal, Trash Compactor, Microwave, Refrigerator, Freezer, Washer, Dryer, Plumbed For Ice Maker
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Dual
Fireplaces Total
1
Flooring
Tile, Carpet, Hardwood, Flooring – Wall to Wall Carpet, Flooring – Hardwood
Heating
Forced Air, Oil
Laundry Features
Second Floor, Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Golf, Bike Path, Highway Access, Public School
Construction Materials
Frame
Exterior Features
Deck, Rain Gutters, Sprinkler System, Gazebo
Other Structures
Gazebo
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
6
Roof
Shingle
Security Features
Security System
Financial
Tax Year
2025
Taxes
$23,217
Map
Contact Us
Mortgage Calculator
Community
- Address276 High Street Winchester MA
- SubdivisionCox Road / High St Extension neighborhood
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- Located in the Cox Road / High St Extension neighborhood subdivision, 276 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,299,000 and features 5 beds, 4 baths, and has approximately 5,006 square feet of living space, and was originally constructed in 1992. The current price per square foot is $459. The average price per square foot for Single Family listings in Winchester is $551. The average listing price for Single Family in Winchester is $2,270,911. To schedule a showing of MLS#73404344 at 276 High Street in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
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CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Compass. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
276 High Street
Winchester, MA