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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.
Current real estate data for Single Family in Winchester as of Dec 30, 2025
37
Single Family Listed
87
Avg DOM
572
Avg $ / SqFt
$1,876,481
Avg List Price

Property Details

Price:
$949,000
MLS #:
73454629
Status:
Pending
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
PoolTennisVinson-owen Elementary SchoolMccall Middle SchoolWinchester High School

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
2
Roof
Shingle

Financial

Tax Year
2025
Taxes
$11,646

Map

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Community

Property Summary

    41 Squire Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $949,000 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 $439. The average price per square foot for Single Family listings in Winchester is $572. The average listing price for Single Family in Winchester is $1,876,481. 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 James
41 Squire Road
Winchester, MA