Google street view image for 39 Kenwin Rd, Winchester, MA 01890

Off Market Dec 1990 for $214K

$1,425,401

Est. refi paymentEst. refi $1,347/mo

•

2.5 ba

•

2,252

sq ft

39 Kenwin Rd, Winchester, MA 01890

About this home

39 Kenwin Rd is a 2,252 square foot house on a 0.32 acre lot with 4 bedrooms and 2.5 bathrooms. - it last sold on December 20, 1990 for $214,700. Based on Redfin's Winchester data, we estimate the home's value is $1,425,401.

Single-familyProperty Type

1939Year Built

0.32 acresLot Size

$633Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,425,401

$1.2M since sold in December 1990$8,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.3% higher than the average sale price ($1.35M) of 6 comparable homes.

SOLD JUL 6, 2026
$1,620,000
A
4 beds2.5 baths2,233 sq ft
10 Bonad Rd, Winchester, MA 01890
SOLD JUL 9, 2026
$1,750,000
B
4 beds3 baths2,814 sq ft
24 Hinds Rd, Winchester, MA 01890
SOLD JUL 28, 2026
$860,000
C
4 beds3 baths2,200 sq ft
92 Garfield Ave, Woburn, MA 01801
SOLD DEC 1, 2025
$1,425,000
D
4 beds2 baths1,755 sq ft
102 Hillcrest Pkwy, Winchester, MA 01890
SOLD MAY 20, 2026
$1,218,000
E
4 beds2 baths1,841 sq ft
40 Englewood 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

$1,353,758

Est. take-home

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Est. cash available

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Rent

$4,650/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

OPEN THU, 5PM TO 6:30PM
$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
$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
$3,199,000
5 beds4.5 baths5,406 sq ft
10 Rangeley Rd, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$3,295,000
6 beds6.5 baths6,100 sq ft
2 Atherton Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 39 Kenwin Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,769 (+13.0%)

$825,600 + $416,000

$1,241,600

2023

$12,188 (−0.5%)

$717,900 + $415,200

$1,133,100

2022

$12,249 (+3.2%)

$592,300 + $386,800

$979,100

2021

$11,870 (+3.6%)

$538,400 + $386,800

$925,200

2020

$11,463 (+12.6%)

$538,400 + $386,800

$925,200

2019

$10,183 (+3.4%)

$454,100 + $386,800

$840,900

2018

$9,848 (+7.6%)

$432,500 + $375,400

$807,900

2017

$9,156 (+9.6%)

$393,100 + $352,500

$745,600

2016

$8,354 (+5.6%)

$374,200 + $341,000

$715,200

2015

$7,909 (+2.1%)

$340,100 + $311,400

$651,500

2014

$7,749 (+2.9%)

$309,600 + $302,500

$612,100

2013

$7,530 (+1.7%)

$296,100 + $293,600

$589,700

2012

$7,401 (+3.7%)

$296,100 + $293,600

$589,700

2011

$7,135 (+3.5%)

$296,100 + $293,600

$589,700

2010

$6,897 (+2.1%)

$306,900 + $292,300

$599,200

2009

$6,753

$306,900 + $292,300

$599,200

Tax history for 39 Kenwin Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,769 (+13.0%)

$825,600 + $416,000

$1,241,600

2023

$12,188 (−0.5%)

$717,900 + $415,200

$1,133,100

2022

$12,249 (+3.2%)

$592,300 + $386,800

$979,100

2021

$11,870 (+3.6%)

$538,400 + $386,800

$925,200

2020

$11,463 (+12.6%)

$538,400 + $386,800

$925,200

2019

$10,183 (+3.4%)

$454,100 + $386,800

$840,900

2018

$9,848 (+7.6%)

$432,500 + $375,400

$807,900

2017

$9,156 (+9.6%)

$393,100 + $352,500

$745,600

2016

$8,354 (+5.6%)

$374,200 + $341,000

$715,200

2015

$7,909 (+2.1%)

$340,100 + $311,400

$651,500

2014

$7,749 (+2.9%)

$309,600 + $302,500

$612,100

2013

$7,530 (+1.7%)

$296,100 + $293,600

$589,700

2012

$7,401 (+3.7%)

$296,100 + $293,600

$589,700

2011

$7,135 (+3.5%)

$296,100 + $293,600

$589,700

2010

$6,897 (+2.1%)

$306,900 + $292,300

$599,200

2009

$6,753

$306,900 + $292,300

$599,200

*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: 878

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Steam

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Room Information
# of Rooms: 8

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Cape Cod
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 2,252
Gross Sq. Ft: 3,110
# of Units: 1
# of Stories: 2

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

Lot Information
# of Buildings: 1
Land Sq. Ft: 13,939
Municipality Name: WINCHESTER
Acres: 0.32
Zoning Code: RDB
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,252
Stories: 2.0
Lot Size: 0.32 acres
Style: Single Family Residential
Year Built: 1939
Year Renovated: —
County: Middlesex County
APN: 3833119S

Home facts updated by county records on Jul 29, 2026

Around this home

Schools
Places
Transit

Muraco Elementary School

Public K-5 • Assigned • 0.4mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.1mi

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 hot days expected this year, 15 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 9.2 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

$1.36M – $1.64M

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New listings for sale in 01890

OPEN THU, 5PM TO 6:30PM3D WALKTHROUGH

$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

$1,999,000

4 beds2.5 baths3,757 sq ft

85 High St, Winchester, MA 01890

EARLY ACCESSCOMPASS COMING SOON

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

$3,199,000

5 beds4.5 baths5,406 sq ft

10 Rangeley Rd, Winchester, MA 01890

OPEN SAT, 12PM TO 1:30PM

$3,295,000

6 beds6.5 baths6,100 sq ft

2 Atherton Rd, Winchester, MA 01890

Home values near 39 Kenwin Rd

Data from public records.

Address	Redfin Estimate
37 Kenwin Road, Winchester, MA 3 Beds \| 3 Baths \| 1779 Sq. Ft.	$1,464,597
29 Kenwin Road, Winchester, MA 4 Beds \| 2 Baths \| 2132 Sq. Ft.	$1,491,450

Address	Redfin Estimate
35 Kenwin Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1922 Sq. Ft.	$1,293,010
28 Kenwin Road, Winchester, MA 3 Beds \| 1.5 Baths \| 1621 Sq. Ft.	$1,273,136

Address	Redfin Estimate
33 Kenwin Road, Winchester, MA 3 Beds \| 2 Baths \| 1864 Sq. Ft.	$1,412,683
30 Kenwin Road, Winchester, MA 3 Beds \| 1.5 Baths \| 2100 Sq. Ft.	$1,393,566

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