Off market jul 2009 for $995K

$1,973,965

Est. refi paymentEst. refi $6,619/mo

•

2,661

sq ft

18 Chesterford Rd, Winchester, MA 01890

About this home

Beautifully sited on over an acre lot including private peninsula on Winter pond. This unique property provides privacy & the benefits of waterfront living including canoeing, bird watching and winter ice skating. Beautiful details throughout. Water views from Kitchen,LR, Den & updated Master suite. Cathedral ceiling eat-in kitchen, large dining room and fireplaced LR. Vacation everyday in your own home with the convenience of Boston only 20 minutes away.

Single-familyProperty Type

1929Year Built

1.56 acresLot Size

$742Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Caci/Randazzo Team • RE/MAX Leading Edge

Bought with Sven Andersen • RE/MAX Leading Edge

Redfin checked: 2 minutes ago

•Source:MLS PIN #70897367

Redfin Estimate

$1,973,965

$979K since sold in July 2009$27K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 19.1% higher than the average sale price ($1.66M) of 6 comparable homes.

SOLD DEC 15, 2025
$1,549,000
A
3 beds2.5 baths2,587 sq ft
32 Woodside Rd, Winchester, MA 01890
SOLD AUG 14, 2026
$2,200,000
B
4 beds2.5 baths3,123 sq ft
15 Cabot St, Winchester, MA 01890
SOLD AUG 14, 2026
$1,325,000
C
3 beds1.5 baths2,006 sq ft
3 Chesterford Ter, Winchester, MA 01890
SOLD MAY 15, 2026
$2,300,000
D
4 beds2.5 baths3,283 sq ft
12 Yale St, Winchester, MA 01890
SOLD AUG 14, 2026
$1,500,000
E
3 beds2 baths2,387 sq ft
14 Rangeley Rdg, 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

$1,421,135

Est. take-home

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Refinance

Est. cash available

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Rent

$5,304/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 18 Chesterford Rd

Date

Event

Price

MLS PIN #70897367

Jul 23, 2009

Sold

$995,000

$374/sq ft

Apr 18, 2009

Contingent

—

Apr 6, 2009

Relisted

—

Apr 6, 2009

Contingent

—

Apr 2, 2009

Listed

$995,000

$374/sq ft

MLS PIN #30709681

Aug 19, 2003

Sold

$1,020,000

$383/sq ft

May 29, 2003

Listing Removed

—

Apr 14, 2003

Listed

$995,000

$374/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$19,205 (+1.0%)

$1,117,200 + $616,100

$1,733,300

2025

$19,016 (+4.3%)

$1,117,200 + $597,500

$1,714,700

2023

$18,232 (+2.5%)

$1,117,200 + $552,600

$1,669,800

2022

$17,784 (+3.0%)

$906,800 + $514,800

$1,421,600

2021

$17,264 (+14.9%)

$830,800 + $514,800

$1,345,600

2020

$15,024 (+0.7%)

$697,800 + $514,800

$1,212,600

2019

$14,915 (+4.3%)

$716,800 + $514,800

$1,231,600

2018

$14,295 (+1.8%)

$672,200 + $500,500

$1,172,700

2017

$14,047 (+6.5%)

$672,200 + $471,700

$1,143,900

2016

$13,194 (−2.3%)

$672,200 + $457,400

$1,129,600

2015

$13,503 (+3.4%)

$672,200 + $440,100

$1,112,300

2014

$13,055 (+5.1%)

$606,000 + $425,200

$1,031,200

2013

$12,421 (+1.8%)

$559,000 + $413,700

$972,700

2012

$12,207 (+3.7%)

$559,000 + $413,700

$972,700

2011

$11,770 (−1.0%)

$559,000 + $413,700

$972,700

2010

$11,885 (+0.2%)

$581,200 + $451,400

$1,032,600

2009

$11,866

$598,800 + $454,100

$1,052,900

Tax history for 18 Chesterford Rd

Year

Property tax

Land + Additions

Assessment*

2026

$19,205 (+1.0%)

$1,117,200 + $616,100

$1,733,300

2025

$19,016 (+4.3%)

$1,117,200 + $597,500

$1,714,700

2023

$18,232 (+2.5%)

$1,117,200 + $552,600

$1,669,800

2022

$17,784 (+3.0%)

$906,800 + $514,800

$1,421,600

2021

$17,264 (+14.9%)

$830,800 + $514,800

$1,345,600

2020

$15,024 (+0.7%)

$697,800 + $514,800

$1,212,600

2019

$14,915 (+4.3%)

$716,800 + $514,800

$1,231,600

2018

$14,295 (+1.8%)

$672,200 + $500,500

$1,172,700

2017

$14,047 (+6.5%)

$672,200 + $471,700

$1,143,900

2016

$13,194 (−2.3%)

$672,200 + $457,400

$1,129,600

2015

$13,503 (+3.4%)

$672,200 + $440,100

$1,112,300

2014

$13,055 (+5.1%)

$606,000 + $425,200

$1,031,200

2013

$12,421 (+1.8%)

$559,000 + $413,700

$972,700

2012

$12,207 (+3.7%)

$559,000 + $413,700

$972,700

2011

$11,770 (−1.0%)

$559,000 + $413,700

$972,700

2010

$11,885 (+0.2%)

$581,200 + $451,400

$1,032,600

2009

$11,866

$598,800 + $454,100

$1,052,900

*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

1.56 Acres

Year renovated

—

Sq. Ft.

2,661

Year built

1929

Style

Single Family Residential

County

Middlesex County

APN

3819480S

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: 2
# of Covered Spaces: 2
Parking Spaces: 4
Parking Features: Detached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 216
Length: 18
Width: 12
Level: Second
Features: Bathroom - Full,Flooring - Hardwood

Bedroom #2 Information
Area: 108
Length: 12
Width: 9
Level: Second
Features: Flooring - Hardwood,Flooring - Wall to Wall Carpet

Bedroom #3 Information
Area: 132
Length: 12
Width: 11
Level: Second
Features: Flooring - Hardwood,Flooring - Wall to Wall Carpet

Bedroom #4 Information
Area: 66
Length: 11
Width: 6
Level: First
Features: Flooring - Hardwood,Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Living Room Information
Area: 396
Length: 22
Width: 18
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 165
Length: 15
Width: 11
Level: First
Features: Flooring - Wall to Wall Carpet

Dining Room Information
Area: 180
Length: 18
Width: 10
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 204
Length: 17
Width: 12
Level: First
Features: Cathedral Ceiling(s),Flooring - Hardwood

Office Room Information
Area: 120
Length: 10
Width: 12
Level: Basement

Basement Information
Basement: Full, Partially Finished

Laundry Information
Laundry Features: Washer Hookup

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

Interior Features
# of Rooms (Total): 10
Door Features: Storm Door(s)
Window Features: Insulated Windows, Storm Window(s), Screens
Flooring: Wood
Interior Features: Game Room, Office

Exterior

Building Information
Building Area (Total): 2,661
Foundation Area: 1,200
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual,Approximate
Color: Grey/Beige

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Screens

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 1.56
Lot Features: Wooded
WaterfrontYN: Yes
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $11,866
Tax Year: 2009

Utilities

Utility Information
Utilities: for Gas Range, Washer Hookup
Sewer: Private Sewer, Private Sewerage
Water Source: Public, City/Town Water
Electric: 220 Volts, Circuit Breakers

Heating & Cooling
Has Heating
Has Cooling
Heating: Central, Baseboard, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Woodside to Chesterford,Pond to Chesterford.
UnparsedAddress: 18 Chesterford Rd, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Walk/Jog Trails, Golf

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,661
Stories: 2.0
Lot Size: 1.56 acres
Style: Single Family Residential
Year Built: 1929
Year Renovated: —
County: Middlesex County
APN: 3819480S

Home facts updated by county records on Sep 16, 2026

Other

Miscellaneous Information
Heat Zones: 5

Listing Information
Exclusions: Dining Room Fixture
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

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

$1.88M – $2.27M

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Home values near 18 Chesterford Rd

Data from public records.

Address	Redfin Estimate
20 Chesterford Road, Winchester, MA 4 Beds \| 1.5 Baths \| 2314 Sq. Ft.	$1,505,905
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 2009. This data may not match . Learn more.

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