Off market apr 2007 for $750K

$1,505,905

Est. refi paymentEst. refi $4,516/mo

•

2,314

sq ft

20 Chesterford Rd, Winchester, MA 01890

About this home

Stunning custom Colonial wih sun-filled living spaces, abundant detail, major state-of-the-art improvements & just steps to Winter Pond. Triple crown moldings. Numerous built-ins. Surround sound. Updated baths. 2002 designer kitchen with granite counters, wood floor, & stainless steel appliances. Large fireplaced media/family room in lower level. Well landscaped, low maintenance lot with fabulous entertainment-size bluestone patio. Staircase to walk-up attic. Parking for 2 cars.

Single-familyProperty Type

1932Year Built

7,080 sq ftLot Size

$651Est. Price/Sq.Ft.

2 spacesParking

Listed by Thea Curtin • Hammond Real Estate

Bought with Cheryl Major • RE/MAX Landmark, Realtors

Redfin checked: a few seconds ago

•Source:MLS PIN #70520211

Redfin Estimate

$1,505,905

$756K since sold in April 2007$42K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 42.7% higher than the average sale price ($1.05M) of 6 comparable homes.

SOLD SEP 18, 2026
$1,035,000
A
4 beds1.5 baths1,777 sq ft
46 Clark St, Winchester, MA 01890
SOLD AUG 14, 2026
$1,325,000
B
3 beds1.5 baths2,006 sq ft
3 Chesterford Ter, Winchester, MA 01890
SOLD BY REDFIN JUN 5, 2026
$1,020,000
C
5 beds2 baths2,331 sq ft
149 Horn Pond Brook Rd, Winchester, MA 01890
SOLD SEP 29, 2026
$800,000
D
4 beds2 baths2,016 sq ft
2 Sonrel St, Woburn, MA 01801
SOLD MAY 12, 2026
$1,080,000
E
4 beds2 baths1,552 sq ft
76 Woodside Rd, Winchester, MA 01890
SOLD MAY 20, 2026
$1,070,000
F
4 beds1.5 baths1,917 sq ft
198 Pond St, Winchester, MA 01890

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Sell

$1,136,272

Est. take-home

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Refinance

Est. cash available

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Rent

$4,891/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 TODAY, 11AM TO 12:30PM
$899,000
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15 Vinson Cir, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$3,299,000
7 beds7.5 baths7,226 sq ft
1 Plymouth Rd, Winchester, MA 01890
OPEN TODAY, 11AM TO 12:30PM
$1,299,000
6 beds2.5 baths3,910 sq ft
8 North Gtwy, Winchester, MA 01890
OPEN TODAY, 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 TODAY, 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 TODAY, 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 20 Chesterford Rd

Date

Event

Price

MLS PIN #70520211

Apr 27, 2007

Sold

$750,000

$324/sq ft

Mar 7, 2007

Listing Removed

—

Feb 2, 2007

Listed

$750,000

$324/sq ft

MLS PIN #50485578

Dec 15, 1997

Sold

$315,000

$136/sq ft

Nov 17, 1997

Listing Removed

—

Oct 15, 1997

Listed

$339,000

$146/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$15,181 (+1.1%)

$866,800 + $503,300

$1,370,100

2025

$15,021 (+10.8%)

$866,800 + $487,700

$1,354,500

2023

$13,551 (+1.9%)

$804,900 + $450,100

$1,255,000

2022

$13,302 (+8.6%)

$650,100 + $413,200

$1,063,300

2021

$12,251 (+7.0%)

$541,700 + $413,200

$954,900

2020

$11,448 (+9.7%)

$510,800 + $413,200

$924,000

2019

$10,440 (+3.8%)

$448,900 + $413,200

$862,100

2018

$10,054 (+5.9%)

$423,300 + $401,500

$824,800

2017

$9,492 (+6.7%)

$398,600 + $374,400

$773,000

2016

$8,895 (+3.0%)

$398,600 + $363,000

$761,600

2015

$8,639 (+6.7%)

$362,200 + $349,400

$711,600

2014

$8,099 (+0.6%)

$301,800 + $337,900

$639,700

2013

$8,053 (+1.8%)

$301,800 + $328,800

$630,600

2012

$7,914 (+3.7%)

$301,800 + $328,800

$630,600

2011

$7,630 (+2.6%)

$301,800 + $328,800

$630,600

2010

$7,435 (+2.1%)

$323,500 + $322,500

$646,000

2009

$7,280

$323,500 + $322,500

$646,000

Tax history for 20 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$15,181 (+1.1%)

$866,800 + $503,300

$1,370,100

2025

$15,021 (+10.8%)

$866,800 + $487,700

$1,354,500

2023

$13,551 (+1.9%)

$804,900 + $450,100

$1,255,000

2022

$13,302 (+8.6%)

$650,100 + $413,200

$1,063,300

2021

$12,251 (+7.0%)

$541,700 + $413,200

$954,900

2020

$11,448 (+9.7%)

$510,800 + $413,200

$924,000

2019

$10,440 (+3.8%)

$448,900 + $413,200

$862,100

2018

$10,054 (+5.9%)

$423,300 + $401,500

$824,800

2017

$9,492 (+6.7%)

$398,600 + $374,400

$773,000

2016

$8,895 (+3.0%)

$398,600 + $363,000

$761,600

2015

$8,639 (+6.7%)

$362,200 + $349,400

$711,600

2014

$8,099 (+0.6%)

$301,800 + $337,900

$639,700

2013

$8,053 (+1.8%)

$301,800 + $328,800

$630,600

2012

$7,914 (+3.7%)

$301,800 + $328,800

$630,600

2011

$7,630 (+2.6%)

$301,800 + $328,800

$630,600

2010

$7,435 (+2.1%)

$323,500 + $322,500

$646,000

2009

$7,280

$323,500 + $322,500

$646,000

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

6,970 Sq. Ft.

Year renovated

—

Sq. Ft.

2,399

Year built

1932

Style

Single Family Residential

County

Middlesex County

APN

3450329S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Property details

Parking

Parking Information
Parking Spaces: 2
Parking Features: Off Street

Interior

Master Bedroom Information
Level: Second

Bedroom #2 Information
Level: Second

Bedroom #3 Information
Level: Second

Bedroom #4 Information
Level: Second

Bathroom Information
# of Bathrooms (Full): 1
# of Bathrooms (Half): 1

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full

Living Room Information
Level: First

Family Room Information
Level: Basement

Dining Room Information
Level: First

Kitchen Information
Level: First
Features: Flooring - Hardwood,Countertops - Stone/Granite/Solid

Basement Information
Basement: Full, Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 9
Flooring: Wood
Interior Features: Den

Exterior

Building Information
Building Area (Total): 2,314
Foundation Details: Concrete Perimeter
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.16

Financial

Tax Information
Tax Annual Amount: $6,380.84
Tax Year: 2007

Utilities

Utility Information
Utilities: for Electric Range
Sewer: Public Sewer, City/Town Sewer
Water Source: Public, City/Town Water
Electric: 100 Amp Service

Heating & Cooling
Has Heating
Heating: Steam, Oil

Location

Location Information
Directions: Wildwood to Woodside to Chesterford
UnparsedAddress: 20 Chesterford Road, Winchester MA 01890

Community Information
Senior CommunityYN: No

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,399
Stories: 2.0
Lot Size: 6,970 square feet
Style: Single Family Residential
Year Built: 1932
Year Renovated: —
County: Middlesex County
APN: 3450329S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: Dining Room Chandelier,Washer And Dryer
StandardStatus: Closed

Around this home

Schools

Lynch Elementary School

Public PreK-5 • Assigned • 0.3mi

9/10

McCall Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.0mi

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

Minor risk of being in a wildfire over 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

$1.43M – $1.73M

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Home values near 20 Chesterford Rd

Data from public records.

Address	Redfin Estimate
18 Chesterford Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2661 Sq. Ft.	$1,973,965
12 Chesterford Road, Winchester, MA 4 Beds \| 2 Baths \| 2796 Sq. Ft.	$1,628,389

Address	Redfin Estimate
16 Chesterford Road, Winchester, MA 4 Beds \| 2.5 Baths \| 2946 Sq. Ft.	$1,666,966
10 Chesterford Road, Winchester, MA 2 Beds \| 2 Baths \| 1566 Sq. Ft.	$1,411,799

Address	Redfin Estimate
14 Chesterford Road, Winchester, MA 2 Beds \| 1.5 Baths \| 1989 Sq. Ft.	$1,367,037
25 Chesterford Road, Winchester, MA 4 Beds \| 2 Baths \| 2175 Sq. Ft.	$1,360,993

Property information provided by MLS PIN when last listed in 2007. This data may not match . Learn more.

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