$2,299,000
276 High Street
Winchester, MA, 01890
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!
Property Details
Price:
$2,299,000
MLS #:
73496396
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Cox Road / High St Extension neighborhood
Listed Date:
Apr 6, 2026
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
Above Grade Finished Area
4267
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
Below Grade Finished Area
739
Cooling
Central Air, Dual
Fireplaces Total
1
Flooring
Tile, Carpet, Hardwood, Flooring – Wall to Wall Carpet, Flooring – Hardwood
Heating
Forced Air, Oil
Interior Features
Bathroom – Tiled With Shower Stall, Bathroom – Full, Bathroom – With Shower Stall, Recessed Lighting, Closet, Lighting – Overhead, Bathroom, Game Room, Office, Central Vacuum, Walk-up Attic
Laundry Features
Second Floor, Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Colonial
Attached Garage YN
1
Community Features
Public Transportation, Shopping, Tennis Court(s), Park, Golf, Bike Path, Highway Access, Public School
Construction Materials
Frame
Covered Spaces
3
Exterior Features
Deck, Rain Gutters, Sprinkler System, Gazebo
Garage Spaces
3
Green Energy Efficient
Thermostat
Open Parking Spaces
6
Open Parking YN
1
Other Structures
Gazebo
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
9
Parking Total
9
Patio And Porch Features
Deck
Roof
Shingle
Security Features
Security System
Window Features
Insulated Windows
Financial
Tax Year
2025
Taxes
$23,217
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of May 04, 2026
71
Single Family Listed
48
Avg DOM
548
Avg $ / SqFt
$2,185,977
Avg List Price
Community
- Address276 High Street Winchester MA
- SubdivisionCox Road / High St Extension neighborhood
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
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 $548. The average listing price for Single Family in Winchester is $2,185,977. To schedule a showing of MLS#73496396 at 276 High Street in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy 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