Google street view image for 27 Squire Rd, Winchester, MA 01890

Off market sep 1977 for $72K

$1,197,961

Est. refi paymentEst. refi $476/mo

•

2 ba

•

1,816

sq ft

27 Squire Rd, Winchester, MA 01890

About this home

27 Squire Rd is a 1,816 square foot house on a 0.73 acre lot with 3 bedrooms and 2 bathrooms. - it last sold on September 28, 1977 for $72,000. Based on Redfin's Winchester data, we estimate the home's value is $1,197,961.

Single-familyProperty Type

1958Year Built

0.73 acresLot Size

$660Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,197,961

$1.1M since sold in September 1977$12K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 20.4% higher than the average sale price ($995K) of 6 comparable homes.

SOLD APR 27, 2026
$1,240,000
A
3 beds2 baths2,087 sq ft
12 Thornberry Rd, Winchester, MA 01890
SOLD JUL 16, 2026
$837,000
B
3 beds2 baths1,812 sq ft
46 Robinson Rd, Woburn, MA 01801
SOLD OCT 2, 2026
$650,000
C
3 beds1.5 baths1,923 sq ft
254 Cambridge Rd, Woburn, MA 01801
SOLD SEP 24, 2026
$1,100,000
D
3 beds2 baths1,736 sq ft
38 Robinhood Rd, Winchester, MA 01890
SOLD JUL 30, 2026
$770,000
E
3 beds1.5 baths1,498 sq ft
31 Hiawatha Rd, Woburn, MA 01801
SOLD MAR 20, 2026
$1,375,000
F
3 beds1.5 baths2,351 sq ft
19 Cox Rd, Winchester, MA 01890

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Earn from this home

Sell

$1,137,590

Est. take-home

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Est. cash available

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Rent

$4,156/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.0%

0.0% MoM

Median sale price

$1.8M

$87K MoM

Avg. days on market

22d

1 days MoM

Recently sold homes

14 MoM

New listings for sale

OPEN SAT, 11:30AM TO 1PM
$2,650,000
4 beds4.5 baths5,233 sq ft
18 Middlesex St, Winchester, MA 01890
NEW 25 HRS AGO
$3,799,000
8 beds5 baths7,081 sq ft
15 Foxcroft Rd, Winchester, MA 01890
OPEN FRI, 12PM TO 1PM
$1,299,000
6 beds2 baths2,946 sq ft
419-421 Washington St, Winchester, MA 01890
$2,950,000
6 beds4 baths4,752 sq ft
18 Surrey Rd, Winchester, MA 01890
EARLY ACCESS
$4,199,000
6 beds6 baths7,175 sq ft
7 Aquinas Path, Winchester, MA 01890
OPEN SUN, 11:30AM TO 1PM
$890,000
2 beds1 bath1,489 sq ft
80 Nelson St, Winchester, MA 01890
OPEN SUN, 1PM TO 2:30PM
$1,985,000
4 beds3.5 baths4,241 sq ft
30 Surrey Rd, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$1,399,000
3 beds2.5 baths1,975 sq ft
6 Aricia Ln, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 27 Squire Rd

Year

Property tax

Land + Additions

Assessment*

2026

$12,249 (−0.2%)

$807,300 + $298,200

$1,105,500

2025

$12,274 (+11.4%)

$807,300 + $299,500

$1,106,800

2023

$11,014 (−3.0%)

$767,300 + $285,800

$1,053,100

2022

$11,355 (+6.9%)

$606,700 + $301,000

$907,700

2021

$10,619 (+4.8%)

$526,700 + $301,000

$827,700

2020

$10,131 (+9.0%)

$516,700 + $301,000

$817,700

2019

$9,297 (+2.3%)

$466,700 + $301,000

$767,700

2018

$9,090 (+3.0%)

$444,700 + $301,000

$745,700

2017

$8,823 (+10.6%)

$444,700 + $273,800

$718,500

2016

$7,980 (+3.2%)

$436,700 + $246,500

$683,200

2015

$7,732 (−1.1%)

$406,700 + $230,200

$636,900

2014

$7,821 (+8.8%)

$396,700 + $221,100

$617,800

2013

$7,187 (+1.8%)

$341,700 + $221,100

$562,800

2012

$7,063 (+3.7%)

$341,700 + $221,100

$562,800

2011

$6,810 (+2.9%)

$341,700 + $221,100

$562,800

2010

$6,619 (+2.1%)

$348,700 + $226,400

$575,100

2009

$6,481

$348,700 + $226,400

$575,100

Tax history for 27 Squire Rd

Year

Property tax

Land + Additions

Assessment*

2026

$12,249 (−0.2%)

$807,300 + $298,200

$1,105,500

2025

$12,274 (+11.4%)

$807,300 + $299,500

$1,106,800

2023

$11,014 (−3.0%)

$767,300 + $285,800

$1,053,100

2022

$11,355 (+6.9%)

$606,700 + $301,000

$907,700

2021

$10,619 (+4.8%)

$526,700 + $301,000

$827,700

2020

$10,131 (+9.0%)

$516,700 + $301,000

$817,700

2019

$9,297 (+2.3%)

$466,700 + $301,000

$767,700

2018

$9,090 (+3.0%)

$444,700 + $301,000

$745,700

2017

$8,823 (+10.6%)

$444,700 + $273,800

$718,500

2016

$7,980 (+3.2%)

$436,700 + $246,500

$683,200

2015

$7,732 (−1.1%)

$406,700 + $230,200

$636,900

2014

$7,821 (+8.8%)

$396,700 + $221,100

$617,800

2013

$7,187 (+1.8%)

$341,700 + $221,100

$562,800

2012

$7,063 (+3.7%)

$341,700 + $221,100

$562,800

2011

$6,810 (+2.9%)

$341,700 + $221,100

$562,800

2010

$6,619 (+2.1%)

$348,700 + $226,400

$575,100

2009

$6,481

$348,700 + $226,400

$575,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Sq. Ft: 1,152

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Room Information
# of Rooms: 6

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Split Level
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 1,816
Gross Sq. Ft: 3,183
# of Units: 1
# of Stories: 1

Parking & Garage Information
Parking Type: Basement Garage
Garage / Carport Type: Basement

Lot Information
# of Buildings: 1
Land Sq. Ft: 31,799
Municipality Name: WINCHESTER
Acres: 0.73
Zoning Code: RDA
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2026

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,816
Stories: 1.0
Lot Size: 0.73 acres
Style: Single Family Residential
Year Built: 1958
Year Renovated: —
County: Middlesex County
APN: 3411196S

Home facts updated by county records on Sep 16, 2026

Around this home

Schools

Vinson-Owen Elementary School

Public PreK-5 • Assigned • 0.4mi

9/10

McCall Middle School

Public 6-8 • Assigned • 2.4mi

9/10

Winchester High School

Public 9-12 • Assigned • 2.4mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

4/10 Heat Factor

7 hot days expected this year, 14 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

Air Factor

We're working on getting current and accurate air risk information for this home.

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

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.14M – $1.38M

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OPEN SUN, 1PM TO 2:30PM3D & VIDEO TOUR

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Home values near 27 Squire Rd

Data from public records.

Address	Redfin Estimate
36 Squire Road, Winchester, MA 3 Beds \| 3 Baths \| - Sq. Ft.	$1,314,557
26 Squire Road, Winchester, MA 3 Beds \| 2.5 Baths \| - Sq. Ft.	$1,292,463

Address	Redfin Estimate
32 Squire Road, Winchester, MA 3 Beds \| 2.5 Baths \| 2413 Sq. Ft.	$1,417,109
24 Squire Road, Winchester, MA 2 Beds \| 1.5 Baths \| 1391 Sq. Ft.	$1,230,374

Address	Redfin Estimate
30 Squire Road, Winchester, MA 5 Beds \| 2 Baths \| - Sq. Ft.	$1,265,426
22 Squire Road, Winchester, MA 4 Beds \| 2 Baths \| 2272 Sq. Ft.	$1,270,983

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