Berkshire Drive, to Thornberry Road, to Squire Road
Home type
Single Family Residence
Interior living area
4,450 sqft
Year built
2016
Lot size
25,687 sqft (about 0.59 acres)
Parking spaces
8
Price per sqft
$517/sqft
About this home
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
Listed by Anthony Marino · The Marino Group Collection MLS PIN #73555666 · Updated 10/29/2026, 3:34:00 PM ET
Facts & features
Home overview
Property subtype
Single Family Residence
Property category
Residential
MLS status
Price Changed
Bedrooms
4
Full bathrooms
4
Half bathrooms
1
Total bathrooms
4.5
Total rooms
12
Living area
4,450 sqft
Living area source
Other
Above grade finished area
3,500 sqft
Below grade finished area
950 sqft
Building area
4,450
Building area units
Square Feet
Building area source
Other
Area includes basement
Yes
Interior & systems
Heating
Central · Forced Air · Heat Pump · Electric · Propane
Heating available
Yes
Heating zones
3
Cooling
Central Air · Heat Pump · 3 or More · High Seer Heat Pump (12+)
Cooling available
Yes
Cooling zones
3
Appliances
Water Heater · Tankless Water Heater · Range · Oven · Disposal · Microwave · Refrigerator · Freezer · Washer · Dryer · Plumbed For Ice Maker
Bathroom - Full · Wet bar · Closet/Cabinets - Custom Built · Home Office · Play Room · Exercise Room · Mud Room · Wet Bar
Laundry
Second Floor · Electric Dryer Hookup
Basement
Full · Finished · Walk-Out Access · Interior Entry · Garage Access · Radon Remediation System
Fireplace
Yes
Fireplaces
2
Electrical service
Circuit Breakers
Windows
Insulated Windows
Primary bathroom features
Yes
Room details
Primary bedroom
Level
Second
Features
Bathroom - Full · Flooring - Hardwood
Bedroom 2
Level
Second
Features
Flooring - Hardwood
Bedroom 3
Level
Second
Features
Flooring - Hardwood
Bedroom 4
Level
Second
Features
Flooring - Hardwood
Living room
Level
First
Features
Flooring - Hardwood
Dining room
Level
First
Features
Flooring - Hardwood
Family room
Level
Main,First
Features
Closet/Cabinets - Custom Built · Flooring - Hardwood · Wet Bar · Open Floorplan · Slider
Kitchen
Level
First
Features
Flooring - Hardwood
Office
Level
First
Features
Flooring - Hardwood
Construction & condition
Year built
2016
Year built source
Public Records
Year built details
Actual
Architectural style
Colonial
Construction materials
Frame
Foundation
Concrete Perimeter
Roof
Shingle
Attached property
No
Home warranty
No
Energy efficient features
Thermostat
Insulation
Fiberglass
Exterior color
Dark Gray
Accessory dwelling unit
N
Year round use
Yes
Garage & parking
Total parking spaces
8
Parking features
Attached · Under · Off Street · Driveway · Paved
Garage
Yes
Garage spaces
2
Attached garage
Yes
Covered spaces
2
Carport
No
Open parking
Yes
Open parking spaces
6
Lot & outdoor features
Lot area
25,687 sqft (about 0.59 acres)
Lot size
0.59 acres
Reported lot area
0.59
Lot size units
Acres
Lot features
Wooded · Sloped
Exterior features
Deck - Composite · Covered Patio/Deck · Rain Gutters · Professional Landscaping · Sprinkler System · Decorative Lighting · Fenced Yard · Stone Wall · ET Irrigation Controller · Other
Patio & porch
Deck - Composite · Covered
Fencing
Fenced
Spa
No
Waterfront
No
Beachfront
No
Water views
No
Utilities & infrastructure
Water source
Public
Sewer
Public Sewer
Utilities
for Gas Range · for Electric Oven · for Electric Dryer · Icemaker Connection
Sewer district
MWRA
Road frontage
Public · Dead End
Road surface
Paved
Road responsibility
Public Maintained Road
HOA & community
Homeowners association
No
Community features
Public Transportation · Pool · Tennis Court(s) · Walk/Jog Trails · Medical Facility · Bike Path · Conservation Area · House of Worship · T-Station
Senior community
No
Taxes & property records
Annual property tax
$21,963
Tax year
2025
Assessed value
$1,980,400
Parcel number
901790
Zoning
RDA
Registry book
71164
Registry page
163
Location & listed schools
City
Winchester
County
Middlesex
State
MA
ZIP code
01890
Listed elementary school
Vinson Owen
Listed middle school
Mccall
Listed high school
Whs
Directions
Berkshire Drive, to Thornberry Road, to Squire Road
Listing & disclosures
MLS number
73555666
Listing date
2026-08-11
Original entry date
2026-08-11
Status changed
2026-10-29
Listing modified
2026-10-29
Original list price
$2,499,000
Current list price
$2,299,000
List price per sqft
$516.63
Days on market
79
Property market time
79
Listing terms
Contract
Disclosure indicator
N
Lead paint
Unknown
Price & tax details
Current asking price$2,299,000
Original asking price$2,499,000
Listed on2026-08-11
Days on market79
Tax record supplied by MLS
Year
Property tax
Assessed value
2025
$21,963
$1,980,400
These records are supplied by the current listing. Assessed value is not market value; confirm taxes with the local assessor.
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SCHOOLS & EDUCATION
Schools & performance
2026 MA DESE
School names, grades and state-reported measures are listed below.
School name supplied by the listing; confirm with the district.
MLS school names do not guarantee attendance. Assignment can vary by school year, grade and admissions policy; confirm with the district before committing.What do these numbers mean?
DESE accountability percentiles (1–99) compare schools administering similar assessments, using up to two years of indicators. These are not test scores out of 100 or GreatSchools 1–10 ratings. Progress toward targets is a separate state measure. Consider programs, support services and your child’s needs as well.
School names link to available school or district websites.