Google street view image for 4 Chesterford Rd, Winchester, MA 01890

Off market sep 1975 for $47K

$1,709,886

Est. refi paymentEst. refi $317/mo

•

2.5 ba

•

3,466

sq ft

4 Chesterford Rd, Winchester, MA 01890

About this home

4 Chesterford Rd is a 3,466 square foot house on a 0.41 acre lot with 5 bedrooms and 2.5 bathrooms. - it last sold on September 26, 1975 for $47,500. Based on Redfin's Winchester data, we estimate the home's value is $1,709,886.

Single-familyProperty Type

1920Year Built

0.41 acresLot Size

$493Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,709,886

$1.7M since sold in September 1975$84K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 27.6% lower than the average sale price ($2.36M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,200,000
A
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD JUN 9, 2026
$2,100,000
B
6 beds2.5 baths4,104 sq ft
15 Wildwood St, Winchester, MA 01890
SOLD JUN 26, 2026
$3,500,000
C
5 beds3.5 baths5,128 sq ft
50 Oxford St, Winchester, MA 01890
SOLD AUG 21, 2026
$1,775,000
D
5 beds3 baths3,315 sq ft
8 Hawthorne Rd, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
E
4 beds2.5 baths3,283 sq ft
12 Yale St, Winchester, MA 01890
SOLD JUL 21, 2026
$2,300,000
F
5 beds3.5 baths4,744 sq ft
30 Rangeley Rd, Winchester, MA 01890

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Earn from this home

Sell

$1,624,144

Est. take-home

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Est. cash available

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Rent

$5,260/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%

0.9% MoM

Median sale price

$1.7M

$39K MoM

Avg. days on market

21d

3 days MoM

Recently sold homes

7 MoM

New listings for sale

OPEN SAT, 11AM TO 12:30PM
$899,000
3 beds1 bath1,313 sq ft
39 Henry St, Winchester, MA 01890
NEW 33 HRS AGO
$18,000,000
6 beds6.5 baths10,000 sq ft
15 Vinson Cir, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$3,299,000
7 beds7.5 baths7,226 sq ft
1 Plymouth Rd, Winchester, MA 01890
OPEN SAT, 11AM TO 12:30PM
$1,299,000
6 beds2.5 baths3,910 sq ft
8 North Gtwy, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$1,529,000
4 beds3.5 baths2,709 sq ft
25 Arlington St, Winchester, MA 01890
EARLY ACCESS
$2,150,000
5 beds4 baths4,063 sq ft
21 Amberwood Dr, Winchester, MA 01890
OPEN SAT, 11AM TO 12:30PM
$1,950,000
5 beds4 baths3,371 sq ft
26 Mayflower Rd, Winchester, MA 01890
OPEN SUN, 11AM TO 12:30PM
$1,195,000
3 beds1.5 baths2,239 sq ft
4 Stone Ave, Winchester, MA 01890
OPEN SAT, 12PM TO 1:30PM
$1,850,000
4 beds2.5 baths3,092 sq ft
1 Overlook Way, Winchester, MA 01890
$700,000
2 beds2 baths1,240 sq ft
666 Main St #217, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 4 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,022 (+0.9%)

$1,119,400 + $597,400

$1,716,800

2025

$18,857 (+5.9%)

$1,119,400 + $581,000

$1,700,400

2023

$17,805 (+2.8%)

$1,119,400 + $532,800

$1,652,200

2022

$17,313 (+3.3%)

$907,100 + $476,800

$1,383,900

2021

$16,765 (+15.5%)

$829,900 + $476,800

$1,306,700

2020

$14,516 (+0.7%)

$694,800 + $476,800

$1,171,600

2019

$14,422 (+4.6%)

$714,100 + $476,800

$1,190,900

2018

$13,789 (+1.8%)

$668,700 + $462,500

$1,131,200

2017

$13,541 (+6.5%)

$668,700 + $434,000

$1,102,700

2016

$12,714 (−1.9%)

$668,700 + $419,800

$1,088,500

2015

$12,961 (+3.1%)

$668,700 + $398,900

$1,067,600

2014

$12,573 (+5.5%)

$608,000 + $385,100

$993,100

2013

$11,920 (+1.8%)

$559,700 + $373,700

$933,400

2012

$11,714 (+3.7%)

$559,700 + $373,700

$933,400

2011

$11,294 (+5.0%)

$559,700 + $373,700

$933,400

2010

$10,761 (+2.1%)

$568,400 + $366,500

$934,900

2009

$10,536

$568,400 + $366,500

$934,900

Tax history for 4 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,022 (+0.9%)

$1,119,400 + $597,400

$1,716,800

2025

$18,857 (+5.9%)

$1,119,400 + $581,000

$1,700,400

2023

$17,805 (+2.8%)

$1,119,400 + $532,800

$1,652,200

2022

$17,313 (+3.3%)

$907,100 + $476,800

$1,383,900

2021

$16,765 (+15.5%)

$829,900 + $476,800

$1,306,700

2020

$14,516 (+0.7%)

$694,800 + $476,800

$1,171,600

2019

$14,422 (+4.6%)

$714,100 + $476,800

$1,190,900

2018

$13,789 (+1.8%)

$668,700 + $462,500

$1,131,200

2017

$13,541 (+6.5%)

$668,700 + $434,000

$1,102,700

2016

$12,714 (−1.9%)

$668,700 + $419,800

$1,088,500

2015

$12,961 (+3.1%)

$668,700 + $398,900

$1,067,600

2014

$12,573 (+5.5%)

$608,000 + $385,100

$993,100

2013

$11,920 (+1.8%)

$559,700 + $373,700

$933,400

2012

$11,714 (+3.7%)

$559,700 + $373,700

$933,400

2011

$11,294 (+5.0%)

$559,700 + $373,700

$933,400

2010

$10,761 (+2.1%)

$568,400 + $366,500

$934,900

2009

$10,536

$568,400 + $366,500

$934,900

*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: 1,424

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

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 1
Fireplace Type: Wood Stove
Has Fireplace

Room Information
# of Rooms: 10

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Colonial
Construction Type: Frame
Exterior Wall: Shingle
Roof Shape Type: Gambrel

Property Information
Living Sq. Ft: 3,466
Gross Sq. Ft: 5,551
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 17,860
Municipality Name: WINCHESTER
Acres: 0.41
Zoning Code: RDB
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2026

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 3,466
Stories: 2.0
Lot Size: 0.41 acres
Style: Single Family Residential
Year Built: 1920
Year Renovated: —
County: Middlesex County
APN: 3740634S

Home facts updated by county records on Sep 16, 2026

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.2mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.0mi

9/10

Winchester High School

Public 9-12 • Assigned • 0.9mi

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

$1.63M – $1.97M

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New listings for sale in 01890

OPEN SAT, 11AM TO 12:30PM

$899,000

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39 Henry St, Winchester, MA 01890

NEW 33 HRS AGO

$18,000,000

6 beds6.5 baths10,000 sq ft

15 Vinson Cir, Winchester, MA 01890

OPEN SAT, 12PM TO 1:30PM

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7 beds7.5 baths7,226 sq ft

1 Plymouth Rd, Winchester, MA 01890

OPEN SAT, 11AM TO 12:30PM

$1,299,000

6 beds2.5 baths3,910 sq ft

8 North Gtwy, Winchester, MA 01890

OPEN SAT, 12PM TO 1:30PM

$1,529,000

4 beds3.5 baths2,709 sq ft

25 Arlington St, Winchester, MA 01890

EARLY ACCESSCOMPASS COMING SOON

$2,150,000

5 beds4 baths4,063 sq ft

21 Amberwood Dr, Winchester, MA 01890

OPEN SAT, 11AM TO 12:30PM

$1,950,000

5 beds4 baths3,371 sq ft

26 Mayflower Rd, Winchester, MA 01890

OPEN SUN, 11AM TO 12:30PM

$1,195,000

3 beds1.5 baths2,239 sq ft

4 Stone Ave, Winchester, MA 01890

OPEN SAT, 12PM TO 1:30PMVIDEO TOUR

$1,850,000

4 beds2.5 baths3,092 sq ft

1 Overlook Way, Winchester, MA 01890

Home values near 4 Chesterford Rd

Data from public records.

Address	Redfin Estimate
14 Chesterford Rd, Winchester, MA 2 Beds \| 1.5 Baths \| 1989 Sq. Ft.	$1,367,037
6 Chesterford Rd, Winchester, MA 4 Beds \| 2 Baths \| 2264 Sq. Ft.	$1,756,689

Address	Redfin Estimate
12 Chesterford Rd, Winchester, MA 4 Beds \| 2 Baths \| 2796 Sq. Ft.	$1,628,389
9 Chesterford Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 1858 Sq. Ft.	$1,616,734

Address	Redfin Estimate
10 Chesterford Rd, Winchester, MA 2 Beds \| 2 Baths \| 1566 Sq. Ft.	$1,411,799
6 Chesterford Ter, Winchester, MA 4 Beds \| 2.5 Baths \| 2524 Sq. Ft.	$1,615,311

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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 4 Chesterford Rd

Tax history for 4 Chesterford 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 4 Chesterford Rd

More real estate resources