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!
This home has been viewed 6 times
Last Checked: July 9th, 2026 at 9:03am (Source: MLS PIN #73496396)
Garage Parking
Green Features
Air Conditioning
Lead Paint Free
General Information for 276 High Street, Winchester MA 01890
Listing ID73496396
Property TypeSingle Family / Detached
Price$2,195,000 ($438.47/SqFt)
StyleColonial
CityWinchester
CountyMiddlesex
Neighborhood(s)
Garage Parking3
ZoningRDA
Year Built1992
Year Built SourcePublic Records
Year Built DetailsActual
Interior Features for 276 High Street, Winchester MA 01890
Approximate Living Area Total5006
Living Area Includes BasementYes
Rooms11
Bedrooms5
Primary En Suite BathroomYes
BasementFull
Cooling1, Split
Fireplaces
AppliancesRange
FlooringTile
Electric220 Volts
Exterior Features for 276 High Street, Winchester MA 01890
Approximate Lot Size (Acres)0.46
Approximate Lot Size (Square Feet)19998
Total Parking12 (3 Garage)
Garage Parking3
WaterPublic
SewerPublic Sewer
Lot Features
Parking Features1
Exterior FeaturesPorch
Foundation Materials
Construction MaterialsFrame
Road Frontage Type
Patio & PorchCovered
Roof MaterialAsphalt/fiberglass Shingles
Utility Connections110 Volts
Water Views
Water Views Features
Waterfront0
Waterfront Features
Pool Features
Horse Permitted0
Horse Amenities
Disclosures for 276 High Street, Winchester MA 01890
Lead PaintNone
UFFI
Living Area Includes BasementYes
Living Area Disclosure
Building Area SourcePublic Records
Special Listing Conditions
ExclusionsPersonal Property
Compensation Based On
Financial Information for 276 High Street, Winchester MA 01890
Association Fee
Association Fee Frequency
Association Fee Includes
Real Estate Tax23217
Tax Year2025
Assessed Value$2,093,500
Location Information for 276 High Street, Winchester MA 01890
Elementary SchoolVinson Owen
Middle SchoolMccall
High SchoolWhs
Neighborhood(s)
Area AmenitiesWalk/jog Trails
Contact Information for 276 High Street, Winchester MA 01890