This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space. Additional highlights include a one-car garage under and a convenient layout with timeless appeal. Nestled beside conservation land, this home provides a peaceful, natural setting where you can enjoy watching birds and local wildlife right from the yard. Make this one yours for 2026!
Current real estate data for Single Family in Winchester as of Nov 17, 2025
63
Single Family Listed
69
Avg DOM
554
Avg $ / SqFt
$2,056,473
Avg List Price
Property Details
Price:
$999,000
MLS #:
73453920
Status:
Active
Beds:
3
Baths:
1.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Nov 12, 2025
Finished Sq Ft:
1,302
Total Sq Ft:
1,302
Lot Size:
22,120 sqft / 0.51 acres (approx)
Year Built:
1949
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Whs
Interior
Appliances
Electric Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Bathrooms
1 Full Bathroom, 1 Half Bathroom
Cooling
Heat Pump
Fireplaces Total
1
Flooring
Tile, Vinyl, Hardwood
Heating
Heat Pump
Laundry Features
In Basement, Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Cape
Community Features
Public Transportation, Park, Walk/Jog Trails, Golf, Medical Facility, House of Worship, Public School, T-Station
Construction Materials
Frame
Exterior Features
Rain Gutters
Parking Features
Attached, Under, Garage Door Opener, Paved Drive, Off Street, Paved
Parking Spots
2
Roof
Shingle
Financial
Tax Year
2025
Taxes
$11,344
Map
Contact Us
Mortgage Calculator
Community
- Address139 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
- 139 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $999,000 and features 3 beds, 2 baths, and has approximately 1,302 square feet of living space, and was originally constructed in 1949. The current price per square foot is $767. The average price per square foot for Single Family listings in Winchester is $554. The average listing price for Single Family in Winchester is $2,056,473. To schedule a showing of MLS#73453920 at 139 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 Better Homes and Gardens Real Estate – The Shanahan Group. 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.
139 High Street
Winchester, MA