Active
54 Days on market
54 Squire Road Winchester — Photo 1 of 42

54 Squire Road Winchester — Photo 1 of 42

Recent Drop: $51,000

$2,450,000
$2,399,000

$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

This Property
Size (SqFt) →Price →
This Property$539/sqft
Local Avg (Winchester)$542/sqft
1% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$2,499,000
Annual Taxes$21,963

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms12
Fireplaces2
FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
BasementFull, Finished, Walk-Out Access, Interior Entry, Garage Access, Radon Remediation System

Climate & Utilities

HeatingCentral, Forced Air, Heat Pump, Electric, Propane
CoolingCentral Air, Heat Pump, 3 or More, High Seer Heat Pump (12+)
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.59
SqFt Lot25,687
Lot FeaturesWooded, Sloped

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

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4
First
Living RoomDining RoomKitchenOffice
Main,First
Family Room
Living Room
Lvl First

Flooring - Hardwood

Dining Room
Lvl First

Flooring - Hardwood

Kitchen
Lvl First

Flooring - Hardwood

Office
Lvl First

Flooring - Hardwood

Family Room
Lvl Main,First

Closet/Cabinets - Custom Built, Flooring - Hardwood, Wet Bar, Open Floorplan, Slider

Primary Bedroom
Lvl Second

Bathroom - Full, Flooring - Hardwood

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Flooring - Hardwood

Bedroom 4
Lvl Second

Flooring - Hardwood

Property History

Price Drop
$2,399,000

Was $2,450,000

Oct 1, 2026

MLS® 73555666

Price Drop
$2,450,000

Was $2,499,000

Sep 15, 2026

MLS® 73555666

Listed
$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 Provided By

Listing Agent: Anthony Marino

Listing Office: The Marino Group Collection

MLS® Number: 73555666