OPEN TODAY, 12PM TO 1:30PM

For sale

$2,450,000

Est. $15,633/mo —

•

4,450

sq ft

54 Squire Rd, Winchester, MA 01890

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

Single-familyProperty Type

2016Year Built

0.59 acresLot Size

$551Price/Sq.Ft.

2 garage spacesParking

Listed by Anthony Marino • The Marino Group Collection

Listing updated: Sep 19, 2026 at 03:07am

Redfin checked: a minute ago

•Source:MLS PIN #73555666

Payment calculator

$15,633 per month

Principal and interest$13,537

Property taxes

$1,830

HOA dues

Home insurance

$265

Utilities

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Open houses

Saturday, Sep 26

12:00pm - 1:30pm

Sunday, Sep 27

12:00pm - 1:30pm

Nearby open houses (10)

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Around this home

Schools

K - 12
Preschool & daycare

Vinson-Owen Elementary School

Public PreK-5 • Assigned • 0.2mi

9/10

McCall Middle School

Public 6-8 • Assigned • 2.2mi

9/10

Winchester High School

Public 9-12 • Assigned • 2.3mi

10/10

Provided by GreatSchools

About West

Side

West Side, located between the Aberjona River and the Middlesex Fells Reservation, is a residential and commuter-friendly Winchester neighborhood with leafy side streets and trail-forward green space. The neighborhood’s character concentrates around the Winchester Center area at Main Street and Church Street, where independent cafes, small shops, and the commuter rhythm of the station set the pace. Community pillars include the Winchester Community Music School, the Winchester Unitarian Society’s historic campus, and the Jenks Center. Housing reads as classic New England—Colonial Revivals, Victorians, and well-kept mid-century homes—on walkable blocks with stone walls and mature trees. The Fells’ trailheads and reservoirs shape daily routines, while the river corridor adds a quieter, tucked-away geography. A short ride to the station keeps Boston-bound schedules in view without turning the streetscape into a thoroughfare.

Provided by Walk Score and Local Logic

Offer insights

54 Squire Rd · $2,450,000

Strong offer

$2.43M and above

75% chance or better to win

Why $2.43M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 22 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Interior features
12 total rooms
Full bathrooms (multiple)
Wet bar
Custom built closets/cabinets
Home office
Play room
Exercise room
Mud room
Insulated windows

Bedrooms
Master bedroom on second floor with full bathroom
Additional bedrooms on second floor

Bathrooms
4 full bathrooms
1 half bathroom
Master bathroom present

Kitchen
Range
Oven
Microwave
Refrigerator
Freezer
Disposal
Plumbed for ice maker
Hardwood flooring in kitchen

Laundry & utility
Washer
Dryer
Second-floor laundry
Electric dryer hookup
Tankless water heater
Water heater

Flooring
Hardwood flooring throughout many rooms
Tile
Wall-to-wall carpet
Stone/ceramic tile

Heating & cooling
Central heating and cooling
Forced air
Heat pump (also used for cooling)
Electric and propane heating options
High-SEER heat pump
Multiple heat zones (3)

Sale and tax history for 54 Squire Rd

Sale History
Tax History

Date

Event

Price

MLS PIN #73555666

Sep 15, 2026

Price Changed

$2,450,000

$551/sq ft

Aug 11, 2026

Listed

$2,499,000

$562/sq ft

MLS PIN #72226558

Jun 15, 2018

Sold

$1,650,000

$371/sq ft

Apr 5, 2018

Pending

—

Mar 31, 2018

Relisted

—

Mar 30, 2018

Listing Removed

—

Nov 1, 2017

Relisted

—

Oct 16, 2017

Listing Removed

—

Sep 11, 2017

Listed

$1,699,900

$382/sq ft

+25

Introducing 54 Squire Road. Featuring high-end NEW construction. Sunny Colonial home nestled away in a private enclave of Winchester. 1st flr has 9 ft ceilings, beautiful crown moldings throughout & offers a large open floor plan. Beautiful chef's kitchen w/ SS appliances, granite counters, double sinks and lots of cabinetry. Sunny breakfast room opens to a large outdoor patio with fire-pit which is ideal for entertaining. Generous sized family room w/ fireplace & built-in bar w/wine fridge. The dining rm w/ lots of windows & walk-thru butlers pantry. Formal living room w/ gas fireplace. Office or 1st-floor bedroom adjacent to 1/2 bath. Large master suite w/ vaulted ceiling, large walk-in closets & spa bath w/ soaking tub. Lower level has a bonus room w/ 3/4 bath, storage, mudroom w/built-ins & 2 car garage. Very large private wooded lot landscaped and ample green spaces to enjoy. Walk to new V.O, Swim & Tennis club. Too many features to list. This is the one you have been waiting for!

MLS PIN #72073186

Dec 15, 2016

Sold

$1,650,000

$371/sq ft

Oct 24, 2016

Pending

—

Sep 26, 2016

Listed

$1,699,999

$382/sq ft

+24

Introducing 54 Squire Road. Featuring high-end new construction. Sunny Colonial home nestled away in a private enclave of Winchester. 1st flr has 9 ft ceilings, beautiful crown moldings throughout & offers a large open floor plan. Beautiful chef's kitchen w/ SS appliances, granite counters, double sinks and lots of cabinetry. Sunny breakfast room opens to a large outdoor patio with fire-pit which is ideal for entertaining. Generous sized family room w/ fireplace & built-in bar w/wine fridge. The dining rm w/ lots of windows & walk-thru butlers pantry. Formal living room w/ gas fireplace. Office or 1st-floor bedroom adjacent to 1/2 bath. Large master suite w/ vaulted ceiling, large walk-in closets & spa bath w/ soaking tub. Lower level has a bonus room w/ 3/4 bath, storage, mudroom w/built-ins & 2 car garage. Very large private wooded lot landscaped and ample green spaces to enjoy. Walk to new V.O, Swim & Tennis club. Too many features to list. This is the one you have been waiting for!

Public Records

Jun 5, 1986

Sold

$257,000

$58/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$22,440 (+2.2%)

$803,600 + $1,221,700

$2,025,300

2025

$21,963 (+4.1%)

$803,600 + $1,176,800

$1,980,400

2024

$21,093 (+3.7%)

$763,600 + $1,098,100

$1,861,700

2023

$20,342 (−0.6%)

$763,600 + $1,098,100

$1,861,700

2022

$20,474 (+2.5%)

$603,300 + $1,033,300

$1,636,600

2021

$19,971 (+4.2%)

$523,300 + $1,033,300

$1,556,600

2020

$19,162 (+1.3%)

$513,300 + $1,033,300

$1,546,600

2019

$18,919 (+2.7%)

$463,300 + $1,099,000

$1,562,300

2018

$18,429 (+50.6%)

$441,300 + $1,070,500

$1,511,800

2017

$12,241 (+54.2%)

$419,400 + $577,400

$996,800

2016

$7,939 (+3.3%)

$411,800 + $267,900

$679,700

2015

$7,686 (−1.6%)

$383,300 + $249,800

$633,100

2014

$7,810 (+9.1%)

$373,800 + $243,100

$616,900

2013

$7,159 (+1.7%)

$321,600 + $239,000

$560,600

2012

$7,036 (+3.7%)

$321,600 + $239,000

$560,600

2011

$6,783 (+1.4%)

$321,600 + $239,000

$560,600

2010

$6,692 (+2.1%)

$328,200 + $253,200

$581,400

2009

$6,552

$328,200 + $253,200

$581,400

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.59 Acres

Year renovated

—

Finished Sq. Ft.

4,409

Unfinished Sq. Ft.

—

Total Sq. Ft.

4,409

Year built

2016

Style

Single Family Residential

County

Middlesex County

APN

3014810S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

50% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

84/ 100

Very good sunlight

Sunscore

This home receives average direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.8 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 54 Squire Rd

$2,378,532

$71K under list price of $2.45M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.7M to $2.6M.

SOLD AUG 21, 2026
$1,775,000 Last sold price
5 beds3 baths3,315 sq ft
8 Hawthorne Rd, Winchester, MA 01890
$16/sq ft
smaller lot
57 years older
SOLD MAY 28, 2026
$2,125,000 Last sold price
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44 Tyler Rd, Lexington, MA 02420
$103/sq ft
larger lot
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SOLD NOV 21, 2025
$2,600,000 Last sold price
5 beds3.5 baths4,779 sq ft
48 Salisbury St, Winchester, MA 01890
$7/sq ft
smaller lot
78 years older
SOLD SEP 3, 2026
$1,715,000 Last sold price
4 beds3 baths3,366 sq ft
94 Johnson Rd, Winchester, MA 01890
$41/sq ft
larger lot
45 years older
SOLD JUN 29, 2026
$2,549,000 Last sold price
4 beds4 baths5,674 sq ft
10 Viking Rd, Winchester, MA 01890
$102/sq ft
smaller lot
37 years older
SOLD JUL 9, 2026
$1,899,000 Last sold price
5 beds2.5 baths3,278 sq ft
105 Thornberry Rd, Winchester, MA 01890
$28/sq ft
smaller lot
45 years older

Rental earnings

Est. $6,207 per month, based on comparable rentals

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Make a winning offer with the help of a local agent

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Details provided by MLS PIN and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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