54 Squire Road
Winchester, MA, 01890
$2,399,000
Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704
Current real estate data for Single Family in Winchester as of Oct 12, 2026
65
Single Family Listed
61
Avg DOM
568
Avg $ / SqFt
$2,161,597
Avg List Price
Property Details
Price:
$2,399,000
MLS #:
73555666
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Aug 11, 2026
Finished Sq Ft:
4,450
Total Sq Ft:
4,450
Lot Size:
25,687 sqft / 0.59 acres (approx)
Year Built:
2016
Schools
Elementary School:
Vinson Owen
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
3500
Appliances
Water Heater, Tankless Water Heater, Range, Oven, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Plumbed For Ice Maker
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
950
Cooling
Central Air, Heat Pump, 3 or More, High Seer Heat Pump (12+)
Fireplaces Total
2
Flooring
Tile, Carpet, Hardwood, Flooring – Hardwood, Flooring – Wall to Wall Carpet, Flooring – Stone/Ceramic Tile
Heating
Central, Forced Air, Heat Pump, Electric, Propane
Interior Features
Bathroom – Full, Wet bar, Closet/Cabinets – Custom Built, Home Office, Play Room, Exercise Room, Mud Room, Wet Bar
Laundry Features
Second Floor, Electric Dryer Hookup
Exterior
Architectural Style
Colonial
Attached Garage YN
1
Community Features
Public Transportation, Pool, Tennis Court(s), Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, House of Worship, T-Station
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Deck – Composite, Covered Patio/Deck, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Stone Wall, ET Irrigation Controller, Other
Fencing
Fenced
Garage Spaces
2
Green Energy Efficient
Thermostat
Lot Features
Wooded, Sloped
Open Parking Spaces
6
Open Parking YN
1
Parking Features
Attached, Under, Off Street, Driveway, Paved
Parking Spots
8
Parking Total
8
Patio And Porch Features
Deck – Composite, Covered
Roof
Shingle
Window Features
Insulated Windows
Financial
Tax Year
2025
Taxes
$21,963
Map
Contact Us
Mortgage Calculator
Community
- Address54 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
- 54 Squire Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,399,000 and features 4 beds, 5 baths, and has approximately 4,450 square feet of living space, and was originally constructed in 2016. The current price per square foot is $539. The average price per square foot for Single Family listings in Winchester is $568. The average listing price for Single Family in Winchester is $2,161,597. To schedule a showing of MLS#73555666 at 54 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 Marino Real Estate 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.
54 Squire Road
Winchester, MA