257 High Street
Winchester, MA, 01890
$3,299,000
Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add’l BR’s, all generously sized. The expansive lower level features an inviting screened “Florida room” family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or for everyday living and entertaining. Must see this fabulous home~ The ultimate home for hosting!
Current real estate data for Single Family in Winchester as of Oct 27, 2025
61
Single Family Listed
69
Avg DOM
532
Avg $ / SqFt
$2,167,370
Avg List Price
Property Details
Price:
$3,299,000
MLS #:
73426449
Status:
Active
Beds:
5
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
West Side
Listed Date:
Sep 4, 2025
Finished Sq Ft:
7,101
Total Sq Ft:
7,101
Lot Size:
73,015 sqft / 1.68 acres (approx)
Year Built:
1994
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall Middle
High School:
Winchester High
Interior
Appliances
Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
Bathrooms
5 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Fireplaces Total
4
Flooring
Tile, Marble, Hardwood, Flooring – Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wall to Wall Carpet
Heating
Forced Air, Natural Gas, Fireplace
Laundry Features
Flooring – Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
Exterior
Architectural Style
Colonial, Contemporary
Community Features
Walk/Jog Trails, Public School
Construction Materials
Frame
Exterior Features
Porch, Porch – Enclosed, Deck, Patio, Patio – Enclosed, Balcony, Rain Gutters, Sprinkler System
Parking Features
Attached, Paved Drive, Paved
Parking Spots
7
Roof
Shingle
Security Features
Security System
Financial
Tax Year
2025
Taxes
$26,758
Map
Contact Us
Mortgage Calculator
Community
- Address257 High Street Winchester MA
- SubdivisionWest Side
- 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 West Side subdivision, 257 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $3,299,000 and features 5 beds, 6 baths, and has approximately 7,101 square feet of living space, and was originally constructed in 1994. The current price per square foot is $465. The average price per square foot for Single Family listings in Winchester is $532. The average listing price for Single Family in Winchester is $2,167,370. To schedule a showing of MLS#73426449 at 257 High Street in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
Similar Listings Nearby
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.
257 High Street
Winchester, MA