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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
Vinson OwenMccallWinchester

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

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Community

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 James
189 High Street
Winchester, MA