65 High Street
Winchester, MA, 01890
$1,499,999
Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with double sinks, an exclusive-use laundry room, and 3 bedrooms, each with 3 windows for generous natural light. The backyard is private and level for grilling, gardening, and entertaining. The huge 1,165 sq ft basement is your creative space for a playroom, gym, and media room. Great school system (Ambros), and downtown convenience for commuter rail, shops, and restaurants. An amazingly beautiful backyard that’s perfect for outdoor recreation. The seller will gift a pool and a ping-pong table to the new buyer in the playroom.
Current real estate data for Single Family in Winchester as of Mar 13, 2026
45
Single Family Listed
59
Avg DOM
544
Avg $ / SqFt
$2,204,007
Avg List Price
Property Details
Price:
$1,499,999
MLS #:
73485189
Status:
Active
Beds:
6
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Mar 11, 2026
Finished Sq Ft:
2,658
Total Sq Ft:
2,658
Lot Size:
10,001 sqft / 0.23 acres (approx)
Year Built:
1949
Schools
Elementary School:
Ambros
Middle School:
Mccall
High School:
Winchester
Interior
Appliances
Water Heater, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Carpet, Hardwood, Flooring – Wall to Wall Carpet
Heating
Baseboard, Oil
Laundry Features
Second Floor, Electric Dryer Hookup
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Highway Access, House of Worship, Public School, T-Station, Other
Construction Materials
Frame
Exterior Features
Porch – Enclosed, Porch – Screened, Storage
Parking Features
Attached, Paved Drive, Off Street
Parking Spots
5
Roof
Shingle
Financial
Tax Year
2025
Taxes
$13,499
Map
Contact Us
Mortgage Calculator
Community
- Address65 High Street Winchester MA
- 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
- 65 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,499,999 and features 6 beds, 3 baths, and has approximately 2,658 square feet of living space, and was originally constructed in 1949. The current price per square foot is $564. The average price per square foot for Single Family listings in Winchester is $544. The average listing price for Single Family in Winchester is $2,204,007. To schedule a showing of MLS#73485189 at 65 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 Stadium Realty. 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.
65 High Street
Winchester, MA