Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners’ vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest exposure, eat-in kitchen, half bath, and access to the garage. Four bedrooms and full bath upstairs. Above grade finished basement with full windows walks out onto a natural backyard. Desirable west end location on Thornberry Hill. Vinson-Owen Elementary School and Winchester Swim & Tennis Club in the neighborhood. Close proximity to Winchester Center, surrounding towns, shopping, dining, area businesses, events and culture, parks, trails, and conservation lands. Convenient to Downtown Boston. OPEN HOUSE SATURDAY November 15th 12:00 – 1:00.
Current real estate data for Single Family in Winchester as of Nov 17, 2025
63
Single Family Listed
67
Avg DOM
554
Avg $ / SqFt
$2,056,473
Avg List Price
Property Details
Price:
$989,000
MLS #:
73454629
Status:
Active
Beds:
4
Baths:
1.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Nov 13, 2025
Finished Sq Ft:
2,162
Total Sq Ft:
2,162
Lot Size:
15,000 sqft / 0.34 acres (approx)
Year Built:
1958
Schools
Elementary School:
Vinson-Owen Elementary School
Middle School:
Mccall Middle School
High School:
Winchester High School
Interior
Appliances
Water Heater, Oven, Range
Bathrooms
1 Full Bathroom, 1 Half Bathroom
Cooling
None
Fireplaces Total
1
Flooring
Carpet, Hardwood
Heating
Central, Baseboard, Oil
Exterior
Architectural Style
Colonial, Mid-Century Modern
Community Features
Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School
Parking Features
Attached, Paved
Parking Spots
1
Roof
Shingle
Financial
Tax Year
2025
Taxes
$11,646
Map
Contact Us
Mortgage Calculator
Community
- Address41 Squire Road 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
- 41 Squire Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $989,000 and features 4 beds, 2 baths, and has approximately 2,162 square feet of living space, and was originally constructed in 1958. The current price per square foot is $457. 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#73454629 at 41 Squire Road 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 Charlesgate Realty Group, llc. 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.
41 Squire Road
Winchester, MA