Off market may 2010 for $595K

$1,374,355

•

2,062

sq ft

5 Chesterford Rd, Winchester, MA 01890

About this home

What a great spot! Lovely, well maintained single family in a desirable location, steps to Winter Pond. Wonderful Cape with 3+ bedrooms, 2 baths & full basement. Comfortable kitchen with nice patio for easy outdoor dining, formal dining room, fireplace in large living room. Large Family room looking into private yard with lovely garden & patio for summer evenings, entertaining and BBQ's! Hardwood floors, newer heating, elect, windows, paint and more. Showings begin Sunday OH 4/11 1:00 - 3:00

Single-familyProperty Type

1927Year Built

9,221 sq ftLot Size

$667Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Leonard Hanlon • ZipRealty, Inc

Bought with Rebecca Brennan • Shanahan Real Estate Group, LLC

Redfin checked: a few seconds ago

•Source:MLS PIN #71056603

Redfin Estimate

$1,374,355

$779K since sold in May 2010$17K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 19% higher than the average sale price ($1.16M) 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 AUG 14, 2026
$1,500,000
B
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, Winchester, MA 01890
SOLD SEP 16, 2026
$815,000
C
3 beds2 baths2,137 sq ft
31 Day Cir, Woburn, MA 01801
SOLD SEP 18, 2026
$1,035,000
D
4 beds1.5 baths1,777 sq ft
46 Clark St, Winchester, MA 01890
SOLD FEB 25, 2026
$1,156,000
E
3 beds1.5 baths1,608 sq ft
136 Sylvester Ave, Winchester, MA 01890
SOLD SEP 24, 2026
$1,100,000
F
3 beds2 baths1,736 sq ft
38 Robinhood Rd, Winchester, MA 01890

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Earn from this home

Sell

$1,020,242

Est. take-home

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Rent

$4,113/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 5 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,608 (+0.7%)

$908,700 + $319,500

$1,228,200

2025

$13,513 (+6.4%)

$908,700 + $309,800

$1,218,500

2023

$12,697 (+0.4%)

$843,800 + $309,100

$1,152,900

2022

$12,649 (+9.8%)

$681,600 + $329,500

$1,011,100

2021

$11,515 (+7.4%)

$568,000 + $329,500

$897,500

2020

$10,717 (+10.6%)

$535,500 + $329,500

$865,000

2019

$9,689 (+4.1%)

$470,600 + $329,500

$800,100

2018

$9,306 (+5.6%)

$443,800 + $319,600

$763,400

2017

$8,815 (+6.6%)

$417,900 + $299,900

$717,800

2016

$8,268 (+3.5%)

$417,900 + $290,000

$707,900

2015

$7,987 (+7.5%)

$379,700 + $278,200

$657,900

2014

$7,429 (+0.5%)

$316,400 + $270,400

$586,800

2013

$7,393 (+1.8%)

$316,400 + $262,500

$578,900

2012

$7,265 (+3.7%)

$316,400 + $262,500

$578,900

2011

$7,005 (+2.4%)

$316,400 + $262,500

$578,900

2010

$6,842 (+2.1%)

$339,200 + $255,200

$594,400

2009

$6,699

$339,200 + $255,200

$594,400

Tax history for 5 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$13,608 (+0.7%)

$908,700 + $319,500

$1,228,200

2025

$13,513 (+6.4%)

$908,700 + $309,800

$1,218,500

2023

$12,697 (+0.4%)

$843,800 + $309,100

$1,152,900

2022

$12,649 (+9.8%)

$681,600 + $329,500

$1,011,100

2021

$11,515 (+7.4%)

$568,000 + $329,500

$897,500

2020

$10,717 (+10.6%)

$535,500 + $329,500

$865,000

2019

$9,689 (+4.1%)

$470,600 + $329,500

$800,100

2018

$9,306 (+5.6%)

$443,800 + $319,600

$763,400

2017

$8,815 (+6.6%)

$417,900 + $299,900

$717,800

2016

$8,268 (+3.5%)

$417,900 + $290,000

$707,900

2015

$7,987 (+7.5%)

$379,700 + $278,200

$657,900

2014

$7,429 (+0.5%)

$316,400 + $270,400

$586,800

2013

$7,393 (+1.8%)

$316,400 + $262,500

$578,900

2012

$7,265 (+3.7%)

$316,400 + $262,500

$578,900

2011

$7,005 (+2.4%)

$316,400 + $262,500

$578,900

2010

$6,842 (+2.1%)

$339,200 + $255,200

$594,400

2009

$6,699

$339,200 + $255,200

$594,400

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

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

9,148 Sq. Ft.

Year renovated

—

Sq. Ft.

2,062

Year built

1927

Style

Single Family Residential

County

Middlesex County

APN

958349S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 1
# of Covered Spaces: 1
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 165
Length: 11
Width: 15
Features: Flooring - Hardwood,Flooring - Wall to Wall Carpet,Closet/Cabinets - Custom Built

Bedroom #2 Information
Area: 156
Length: 12
Width: 13
Features: Flooring - Hardwood,Flooring - Wall to Wall Carpet,Closet/Cabinets - Custom Built

Bedroom #3 Information
Area: 144
Length: 12
Width: 12
Features: Bathroom - Full,Flooring - Wood

Bathroom Information
# of Bathrooms (Full): 2

Living Room Information
Area: 300
Length: 12
Width: 25
Features: Flooring - Hardwood

Family Room Information
Area: 270
Length: 15
Width: 18
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Closet/Cabinets - Custom Built,French Doors

Dining Room Information
Area: 143
Length: 11
Width: 13
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Closet/Cabinets - Custom Built

Kitchen Information
Area: 198
Length: 11
Width: 18
Features: Dining Area,French Doors,Flooring - Vinyl

Basement Information
Basement: Full, Walk-Out Access, Interior Entry, Bulkhead, Sump Pump, Concrete

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 8
Window Features: Insulated Windows
Flooring: Flooring - Hardwood, Flooring - Wall to Wall Carpet

Exterior

Building Information
Building Area (Total): 2,062
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Sprinkler System, Fenced Yard

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.21
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $6,841.54
Tax Year: 2010

Utilities

Utility Information
Water Source: Public, City/Town Water
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Heating: Central, Steam, Natural Gas

Location

HOA Information
Homeowners Association Membership Not Required

Location Information
Directions: Pond St. to Chesterford Rd, or Wildwood St. to Woodside Rd. to Chesterford Rd
UnparsedAddress: 5 Chesterford Road, Winchester MA 01890

Community Information
Senior CommunityYN: No

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 2,062
Stories: 2.0
Lot Size: 9,148 square feet
Style: Single Family Residential
Year Built: 1927
Year Renovated: —
County: Middlesex County
APN: 958349S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
StandardStatus: Closed

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

2/10 Heat Factor

7 days above 93° expected this year, 16 days in 30 years

4/10 Wind Factor

15% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 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

$1.31M – $1.58M

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EARLY ACCESSCOMPASS COMING SOON

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Home values near 5 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
4 Chesterford Rd, Winchester, MA 5 Beds \| 2.5 Baths \| 3466 Sq. Ft.	$1,709,886

Address	Redfin Estimate
10 Chesterford Rd, Winchester, MA 2 Beds \| 2 Baths \| 1566 Sq. Ft.	$1,411,799
15 Chesterford Rd, Winchester, MA 3 Beds \| 2.5 Baths \| 2137 Sq. Ft.	$1,546,570

Property information provided by MLS PIN when last listed in 2010. This data may not match . Learn more.

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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 5 Chesterford Rd

Tax history for 5 Chesterford Rd

Public record

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 5 Chesterford Rd

More real estate resources