5 Squire Rd
Winchester, MA, 01890
$1,899,000
Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable neighborhood, this fabulous 6-bedroom, 3.5 bath home offers luxury finishes at an exceptional value. The primary suite provides a private escape with a walk-in closet and dual vanity, complemented by three additional second-floor bedrooms—two with walk-in closets—a shared bath, and laundry. A large unfinished attic offers future expansion potential, while the finished lower level adds flexibility with full-size windows, a sixth bedroom, full bath, recreation space, and a mudroom with direct garage entry. Enjoy a landscaped, fenced yard with irrigation, close to top-rated schools.
Current real estate data for Single Family in Winchester as of Feb 16, 2026
36
Single Family Listed
63
Avg DOM
539
Avg $ / SqFt
$2,084,964
Avg List Price
Property Details
Price:
$1,899,000
MLS #:
73471882
Status:
Active Under Contract
Beds:
6
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jan 27, 2026
Finished Sq Ft:
4,696
Total Sq Ft:
4,696
Lot Size:
17,912 sqft / 0.41 acres (approx)
Year Built:
1958
Schools
Interior
Appliances
Water Heater, Oven, Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer, Dryer, Range Hood
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Carpet, Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wall to Wall Carpet
Heating
Central, Forced Air, Oil
Laundry Features
Flooring – Stone/Ceramic Tile, Electric Dryer Hookup, Second Floor
Exterior
Architectural Style
Contemporary
Community Features
Shopping, Pool, Tennis Court(s), Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Public School
Construction Materials
Frame
Exterior Features
Deck – Composite, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard, Stone Wall
Parking Features
Attached, Paved Drive, Off Street, Paved
Parking Spots
6
Roof
Shingle
Financial
Tax Year
2026
Taxes
$20,170
Map
Contact Us
Mortgage Calculator
Community
- Address5 Squire Rd 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
- 5 Squire Rd Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,899,000 and features 6 beds, 4 baths, and has approximately 4,696 square feet of living space, and was originally constructed in 1958. The current price per square foot is $404. The average price per square foot for Single Family listings in Winchester is $539. The average listing price for Single Family in Winchester is $2,084,964. To schedule a showing of MLS#73471882 at 5 Squire Rd 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 Keller Williams Realty Boston Northwest. 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.
5 Squire Rd
Winchester, MA












































