
54 Squire Road Winchester — Photo 1 of 42
Recent Drop: $51,000
$2,399,000
54 Squire Road, Winchester, MA 01890
Winchester, MA 01890
Beds
4
Baths
4.5
SqFt
4,450
Style
Single Family
Built
2016
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
Key facts
It was listed on August 11, 2026. The price has come down from an original $2,499,000 to $2,399,000 across 2 changes, most recently on October 1, 2026. The annual property taxes are $21,963 (2025 tax year). It sits on a 0.59-acre (25,687 sq ft) lot.
Open Houses
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Water Heater • Tankless Water Heater • Range • Oven • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Plumbed For Ice Maker
Neighborhood
Public Transportation • Pool • Tennis Court(s) • Walk/Jog Trails • Medical Facility • Bike Path
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl FirstFlooring - Hardwood
Dining Room
Lvl FirstFlooring - Hardwood
Kitchen
Lvl FirstFlooring - Hardwood
Office
Lvl FirstFlooring - Hardwood
Family Room
Lvl Main,FirstCloset/Cabinets - Custom Built, Flooring - Hardwood, Wet Bar, Open Floorplan, Slider
Primary Bedroom
Lvl SecondBathroom - Full, Flooring - Hardwood
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondFlooring - Hardwood
Bedroom 4
Lvl SecondFlooring - Hardwood
Property History
$2,399,000
Was $2,450,000
Oct 1, 2026
MLS® 73555666
$2,450,000
Was $2,499,000
Sep 15, 2026
MLS® 73555666
$2,499,000
Aug 11, 2026
MLS® 73555666
Questions about this home
When was 54 Squire Road, Winchester listed?
54 Squire Road, Winchester was listed on August 11, 2026.
Has the price of 54 Squire Road, Winchester changed?
The price has come down from an original $2,499,000 to $2,399,000 across 2 changes, most recently on October 1, 2026.
What are the property taxes for 54 Squire Road, Winchester?
The annual property taxes for 54 Squire Road, Winchester are $21,963 (2025 tax year).
How big is the lot at 54 Squire Road, Winchester?
54 Squire Road, Winchester sits on a 0.59-acre (25,687 sq ft) lot.
What is the status of 54 Squire Road, Winchester?
54 Squire Road, Winchester is actively listed for sale.
Population
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Middlesex County
2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,450 sq ft principal dwelling). Lot size: 25,687 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Anthony Marino
Listing Office: The Marino Group Collection
MLS® Number: 73555666







