Google street view image for 37 Woodside Rd, Winchester, MA 01890

Off Market Dec 1986 for $176K

$1,049,178

Est. refi paymentEst. refi $1,116/mo

•

1 ba

•

1,500

sq ft

37 Woodside Rd, Winchester, MA 01890

About this home

37 Woodside Rd is a 1,500 square foot house on a 0.25 acre lot with 3 bedrooms and 1 bathroom. - it last sold on December 30, 1986 for $176,000. Based on Redfin's Winchester data, we estimate the home's value is $1,049,178.

Single-familyProperty Type

1927Year Built

0.25 acresLot Size

$699Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,049,178

$873K since sold in December 1986$2,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.1% lower than the average sale price ($1.24M) of 6 comparable homes.

SOLD AUG 14, 2026
$1,325,000
A
3 beds1.5 baths2,006 sq ft
3 Chesterford Ter, Winchester, MA 01890
SOLD FEB 25, 2026
$1,156,000
B
3 beds1.5 baths1,608 sq ft
136 Sylvester Ave, Winchester, MA 01890
SOLD AUG 14, 2026
$1,500,000
C
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD MAY 28, 2026
$1,100,000
D
3 beds1.5 baths1,675 sq ft
104 Wendell St, Winchester, MA 01890
SOLD MAY 12, 2026
$1,080,000
E
4 beds2 baths1,552 sq ft
76 Woodside Rd, Winchester, MA 01890
SOLD MAY 29, 2026
$1,250,000
F
4 beds2 baths2,046 sq ft
87 Wendell St, Winchester, MA 01890

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Earn from this home

Sell

$996,181

Est. take-home

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Est. cash available

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Rent

$3,399/mo

Redfin rental estimate

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Market trends in 01890, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.0% MoM

Median sale price

$1.4M

$57K MoM

Avg. days on market

20d

0 days MoM

Recently sold homes

14 MoM

New listings for sale

EARLY ACCESS
$1,699,000
3 beds2 baths2,327 sq ft
4 Churchill Rd, Winchester, MA 01890
OPEN TODAY, 12:30PM TO 1:30PM
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
OPEN TODAY, 11:30AM TO 1PM
$1,699,000
5 beds3.5 baths3,180 sq ft
30 Farrow St, Winchester, MA 01890
$1,098,000
3 beds1.5 baths1,657 sq ft
17 Russell Rd, Winchester, MA 01890
OPEN SUN, 12PM TO 1:30PM
$1,999,000
4 beds2.5 baths3,757 sq ft
85 High St, Winchester, MA 01890
EARLY ACCESS
Unknown
3 beds3 baths5,127 sq ft
187 High St, Winchester, MA 01890
$949,999
4 beds2 baths2,326 sq ft
96 Loring Ave, Winchester, MA 01890
OPEN TODAY, 11:30AM TO 1PM
$3,199,000
5 beds4.5 baths5,406 sq ft
10 Rangeley Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 37 Woodside Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,097 (+4.8%)

$840,300 + $160,300

$1,000,600

2023

$10,588 (+2.0%)

$840,300 + $159,900

$1,000,200

2022

$10,385 (+1.3%)

$672,200 + $157,900

$830,100

2021

$10,251 (+3.5%)

$605,000 + $194,000

$799,000

2020

$9,900 (+11.7%)

$605,000 + $194,000

$799,000

2019

$8,862 (+7.0%)

$537,800 + $194,000

$731,800

2018

$8,286 (+13.0%)

$485,700 + $194,000

$679,700

2017

$7,332 (+12.5%)

$417,600 + $179,500

$597,100

2016

$6,519 (−1.5%)

$393,200 + $164,900

$558,100

2015

$6,616 (+11.4%)

$393,200 + $151,800

$545,000

2014

$5,941 (+2.0%)

$327,700 + $141,600

$469,300

2013

$5,826 (+1.8%)

$327,700 + $128,500

$456,200

2012

$5,725 (+3.7%)

$327,700 + $128,500

$456,200

2011

$5,520 (+2.0%)

$327,700 + $128,500

$456,200

2010

$5,412 (+2.1%)

$327,200 + $143,000

$470,200

2009

$5,299

$327,200 + $143,000

$470,200

Tax history for 37 Woodside Rd

Year

Property tax

Land + Additions

Assessment*

2025

$11,097 (+4.8%)

$840,300 + $160,300

$1,000,600

2023

$10,588 (+2.0%)

$840,300 + $159,900

$1,000,200

2022

$10,385 (+1.3%)

$672,200 + $157,900

$830,100

2021

$10,251 (+3.5%)

$605,000 + $194,000

$799,000

2020

$9,900 (+11.7%)

$605,000 + $194,000

$799,000

2019

$8,862 (+7.0%)

$537,800 + $194,000

$731,800

2018

$8,286 (+13.0%)

$485,700 + $194,000

$679,700

2017

$7,332 (+12.5%)

$417,600 + $179,500

$597,100

2016

$6,519 (−1.5%)

$393,200 + $164,900

$558,100

2015

$6,616 (+11.4%)

$393,200 + $151,800

$545,000

2014

$5,941 (+2.0%)

$327,700 + $141,600

$469,300

2013

$5,826 (+1.8%)

$327,700 + $128,500

$456,200

2012

$5,725 (+3.7%)

$327,700 + $128,500

$456,200

2011

$5,520 (+2.0%)

$327,700 + $128,500

$456,200

2010

$5,412 (+2.1%)

$327,200 + $143,000

$470,200

2009

$5,299

$327,200 + $143,000

$470,200

*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: 1,500

Bathroom Information
# of Full Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Room Information
# of Rooms: 6

Exterior

Exterior Information
Physical Condition: Poor
Building Style Type: Cottage/Bungalow
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Hip

Property Information
Living Sq. Ft: 1,500
Gross Sq. Ft: 3,072
# 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: 10,890
Municipality Name: WINCHESTER
Acres: 0.25
Zoning Code: RDB
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,500
Stories: 1.0
Lot Size: 0.25 acres
Style: Single Family Residential
Year Built: 1927
Year Renovated: —
County: Middlesex County
APN: 3415447S

Home facts updated by county records on Jul 29, 2026

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.2mi

9/10

McCall Middle School

Public 6-8 • Assigned • 0.9mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.8mi

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

5/10 Heat Factor

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

6/10 Wind Factor

54% 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

In this area, properties receive around 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$997,000 – $1.21M

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3 beds3 baths5,127 sq ft

187 High St, Winchester, MA 01890

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4 beds2 baths2,326 sq ft

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OPEN TODAY, 11:30AM TO 1PM

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Home values near 37 Woodside Rd

Data from public records.

Address	Redfin Estimate
32 Woodside Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2587 Sq. Ft.	$1,775,311
46 Woodside Rd, Winchester, MA 5 Beds \| 3.5 Baths \| 3735 Sq. Ft.	$2,109,600

Address	Redfin Estimate
30 Woodside Rd, Winchester, MA 3 Beds \| 1 Baths \| 1613 Sq. Ft.	$1,167,578
48 Woodside Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 1818 Sq. Ft.	$1,350,663

Address	Redfin Estimate
40 Woodside Rd, Winchester, MA 3 Beds \| 2 Baths \| 1592 Sq. Ft.	$1,267,420
50 Woodside Rd, Winchester, MA 4 Beds \| 2.5 Baths \| 2376 Sq. Ft.	$1,435,398

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 01890, MA

Sale history for 37 Woodside Rd

Tax history for 37 Woodside Rd

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01890

Home values near 37 Woodside Rd

More real estate resources