189 High Street
Winchester, MA, 01890
$1,150,000
This classic Cape offers exceptional space, character, and room to make it your own. The first floor features a gracious front-to-back living room, formal dining room, and an inviting eat-in kitchen, all highlighted by hardwood floors, high ceilings, and a seamless circular layout ideal for everyday living. A charming breezeway connects directly to the one-car garage, adding easy functionality. Upstairs, you’ll find four comfortable bedrooms and a full bath. The finished lower level provides two additional rooms and a brand-new full bath – perfect for guests, a gym, or a home office. Situated on just under a half-acre lot, this home offers endless possibilities for future expansion. Ideally located 1/2 mile to one of Winchester’s most sought after elementary school and minutes from the beloved Wright-Locke Farm. This is the perfect place to make your home!
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:
$1,150,000
MLS #:
73451954
Status:
Active Under Contract
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Nov 6, 2025
Finished Sq Ft:
2,126
Total Sq Ft:
2,126
Lot Size:
20,974 sqft / 0.48 acres (approx)
Year Built:
1951
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Winchester
Interior
Appliances
Range, Dishwasher, Refrigerator, Washer, Dryer
Bathrooms
3 Full Bathrooms
Cooling
None
Fireplaces Total
1
Flooring
Vinyl, Carpet, Laminate, Hardwood, Flooring – Hardwood
Heating
Baseboard, Oil
Laundry Features
In Basement
Exterior
Architectural Style
Cape
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, Public School, T-Station
Parking Features
Attached, Storage, Paved Drive, Off Street
Parking Spots
5
Security Features
Security System
Financial
Tax Year
2025
Taxes
$13,239
Map
Contact Us
Mortgage Calculator
Community
- Address189 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
- 189 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,150,000 and features 4 beds, 3 baths, and has approximately 2,126 square feet of living space, and was originally constructed in 1951. The current price per square foot is $541. 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#73451954 at 189 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.
189 High Street
Winchester, MA











































