Google street view image for 255 Chestnut St, Winnetka, IL 60093

Off market

$1,574,839

•

2.5 ba

•

2,140

sq ft

255 Chestnut St, Winnetka, IL 60093

About this home

255 Chestnut St is a 2,140 square foot house on a 0.28 acre lot with 4 bedrooms and 2.5 bathrooms. Based on Redfin's Winnetka data, we estimate the home's value is $1,574,839.

Single-familyProperty Type

1954Year Built

0.28 acresLot Size

$736Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,574,839

$2,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.7% lower than the average sale price ($1.67M) of 6 comparable homes.

SOLD SEP 15, 2026
$1,700,000
A
4 beds2.5 baths3,653 sq ft
854 Ash St, Winnetka, IL 60093
SOLD JUL 29, 2026
$1,750,000
B
4 beds3.5 baths3,364 sq ft
478 Sunset Rd, Winnetka, IL 60093
SOLD SEP 15, 2026
$1,850,000
C
4 beds2.5 baths3,973 sq ft
922 Ash St, Winnetka, IL 60093
SOLD APR 30, 2026
$1,515,000
D
4 beds2.5 baths2,116 sq ft
916 Oak St, Winnetka, IL 60093
SOLD AUG 31, 2026
$1,650,000
E
4 beds3.5 baths3,251 sq ft
1062 Ash St, Winnetka, IL 60093
SOLD SEP 25, 2026
$1,555,000
F
4 beds2.5 baths— sq ft
919 Oak St, Winnetka, IL 60093

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,500,109

Est. take-home

List your home with Redfin and save $7,874

Rent

$3,343/mo

Redfin rental estimate

List your home for rent

Market trends in 60093, IL

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

104.0%

0.1% MoM

Median sale price

$1.7M

$42K MoM

Avg. days on market

36d

2 days MoM

Recently sold homes

15 MoM

New listings for sale

OPEN SAT, 11AM TO 1PM
$2,750,000
5 beds5 baths7,736 sq ft
936 Fisher Ln, Winnetka, IL 60093
NEW
$2,250,000
4 beds4.5 baths4,225 sq ft
42 Woodley Rd, Winnetka, IL 60093
$525,000
2 beds1.5 baths1,328 sq ft
602 Lincoln Ave, Winnetka, IL 60093
EARLY ACCESS
$1,350,000
3 beds2.5 baths— sq ft
16 Regent Wood Rd, Northfield, IL 60093
$2,195,000
4 beds3.5 baths2,889 sq ft
1036 Ash St, Winnetka, IL 60093
$314,900
2 beds2 baths1,200 sq ft
1709 Northfield Sq Unit B, Northfield, IL 60093
EARLY ACCESS
$899,000
3 beds2 baths2,041 sq ft
7030 Arbor Ln, Northfield, IL 60093
EARLY ACCESS
$2,295,000
5 beds3 baths2,642 sq ft
510 Ash St, Winnetka, IL 60093
EARLY ACCESS
$2,495,000
4 beds4.5 baths4,509 sq ft
1140 Oakley Ave, Winnetka, IL 60093
$775,000
2 beds2.5 baths2 sq ft
1865 Old Willow Rd #224, Northfield, IL 60093
See all

Provided by Redfin

Sale history for 255 Chestnut St

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$20,240 (−2.1%)

$33,956 + $66,044

$100,000

2022

$20,675 (+39.2%)

$33,349 + $64,799

$98,148

2021

$14,847 (+1.2%)

$24,254 + $36,287

$60,541

2020

$14,669 (+0.8%)

$24,254 + $36,287

$60,541

2019

$14,546 (−19.4%)

$24,254 + $41,552

$65,806

2018

$18,044 (−2.4%)

$20,615 + $58,047

$78,662

2017

$18,490 (+3.8%)

$20,615 + $62,305

$82,920

2016

$17,805 (+10.7%)

$20,615 + $62,305

$82,920

2015

$16,087 (+2.1%)

$16,977 + $51,032

$68,009

2014

$15,755 (+4.9%)

$16,977 + $51,032

$68,009

2013

$15,013 (−13.2%)

$16,977 + $51,032

$68,009

2012

$17,290 (+4.4%)

$18,796 + $62,788

$81,584

2011

$16,561 (+8.7%)

$18,796 + $62,788

$81,584

2010

$15,243 (+0.7%)

$18,796 + $62,788

$81,584

2009

$15,132 (+7.0%)

$19,100 + $73,563

$92,663

2008

$14,137 (+7.2%)

$30,560 + $66,981

$97,541

2007

$13,190

$30,560 + $66,981

$97,541

Tax history for 255 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$20,240 (−2.1%)

$33,956 + $66,044

$100,000

2022

$20,675 (+39.2%)

$33,349 + $64,799

$98,148

2021

$14,847 (+1.2%)

$24,254 + $36,287

$60,541

2020

$14,669 (+0.8%)

$24,254 + $36,287

$60,541

2019

$14,546 (−19.4%)

$24,254 + $41,552

$65,806

2018

$18,044 (−2.4%)

$20,615 + $58,047

$78,662

2017

$18,490 (+3.8%)

$20,615 + $62,305

$82,920

2016

$17,805 (+10.7%)

$20,615 + $62,305

$82,920

2015

$16,087 (+2.1%)

$16,977 + $51,032

$68,009

2014

$15,755 (+4.9%)

$16,977 + $51,032

$68,009

2013

$15,013 (−13.2%)

$16,977 + $51,032

$68,009

2012

$17,290 (+4.4%)

$18,796 + $62,788

$81,584

2011

$16,561 (+8.7%)

$18,796 + $62,788

$81,584

2010

$15,243 (+0.7%)

$18,796 + $62,788

$81,584

2009

$15,132 (+7.0%)

$19,100 + $73,563

$92,663

2008

$14,137 (+7.2%)

$30,560 + $66,981

$97,541

2007

$13,190

$30,560 + $66,981

$97,541

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

Zoning

Single-Family Residential District

The requirements set forth in this chapter, together with other provisions set forth in the Building Code of the Village, have been adopted in order to provide for a single-family residential environment of moderately intense suburban character, where the degree of improvements upon an individual parcel of land is generally subordinate to the landscape. Due to the mature character of development within this district, such requirements are also intended to assure that future modifications to existing structures, or the replacement of existing structures with new structures, will not alter the scale and general character of established neighborhoods. In this regard, the requirements set forth in this chapter are further intended to foster development which is compatible, in general, with the character of existing single-family development within the immediate neighborhood with respect to external architectural scale, landscaping and other site improvements.

Permitted uses

Include but are not limited to:

Housing-Single unit

Property details

Interior

Basement Information
Basement Finish: Unfinished
Basement Type: Partial

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

Heating & Cooling
Heating Type: Warm Air

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Old
Exterior Wall: Frame/Masonry
Building Type: Residential

Property Information
Subdivision Name: DALES THIRD WINNETKA
Living Sq. Ft: 2,140
# of Stories: 2
Stories Type: 2
Legal Description: L9 XN33FT & XE6FT B4 DALES 3RD ADDT TO WINNETKA SUBD NE1/4 XNE1/4 SE1/ 4 S20 T42N R13E

Parking & Garage Information
# of Parking Spaces: 1
Parking Type: Attached Garage
Garage / Carport Type: Attached

Lot Information
# of Buildings: 1
Land Sq. Ft: 12,127
Legal Lot Number: 9
Legal Block Number: 4
Acres: 0.2784
Depth Footage: 67
Front Footage: 181
County Use Description: RESID 2 STORY

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,140
Stories: 2.0
Lot Size: 0.28 acres
Style: Single Family Residential
Year Built: 1954
Year Renovated: —
County: Cook County
APN: 05204050290000

Home facts updated by county records on Sep 16, 2026

Around this home

Schools

Crow Island Elementary School

Public K-4 • Assigned • 0.6mi

10/10

Carleton W Washburne School

Public 7-8 • Assigned • 0.9mi

8/10

New Trier Township High School Winnetka

Public 10-12 • Assigned • 0.9mi

8/10

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

2/10 Heat Factor

7 days above 98° expected this year, 14 days in 30 years

2/10 Wind Factor

1% chance of strong winds in next 30 years

3/10 Air Factor

4 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Winnetka, IL • 60093

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 10.3 hours in June and 3.3 hours in December, placing it below the U.S. average for solar exposure.

10.3 hrs

3.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.50M – $1.81M

Reach more buyers when you sell with Redfin. Save up to $15,748 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

VIDEO TOUR

$3,999,000

6 beds7.5 baths6,950 sq ft

1128 Mt. Pleasant Rd, Winnetka, IL 60093

$3,950,000

5 beds6.5 baths5,134 sq ft

2604 Blackhawk Rd, Wilmette, IL 60091

$2,699,000

6 beds5.5 baths— sq ft

82 Woodley Rd, Winnetka, IL 60093

NEW CONSTRUCTION

$16,900,000

6 beds9 baths15,000 sq ft

915 Sunset Rd, Winnetka, IL 60093

OPEN SAT, 11AM TO 1PM

$2,750,000

5 beds5 baths7,736 sq ft

936 Fisher Ln, Winnetka, IL 60093

$2,195,000

4 beds3.5 baths2,889 sq ft

1036 Ash St, Winnetka, IL 60093

New listings for sale in 60093

OPEN SAT, 11AM TO 1PM

$2,750,000

5 beds5 baths7,736 sq ft

936 Fisher Ln, Winnetka, IL 60093

NEW

$2,250,000

4 beds4.5 baths4,225 sq ft

42 Woodley Rd, Winnetka, IL 60093

$525,000

2 beds1.5 baths1,328 sq ft

602 Lincoln Ave, Winnetka, IL 60093

EARLY ACCESS@PROPERTIES COMING SOON

$1,350,000

3 beds2.5 baths— sq ft

16 Regent Wood Rd, Northfield, IL 60093

$2,195,000

4 beds3.5 baths2,889 sq ft

1036 Ash St, Winnetka, IL 60093

$314,900

2 beds2 baths1,200 sq ft

1709 Northfield Sq Unit B, Northfield, IL 60093

EARLY ACCESSCOMPASS COMING SOON

$899,000

3 beds2 baths2,041 sq ft

7030 Arbor Ln, Northfield, IL 60093

EARLY ACCESSCOLDWELL BANKER COMING SOON

$2,295,000

5 beds3 baths2,642 sq ft

510 Ash St, Winnetka, IL 60093

EARLY ACCESSSOTHEBY'S REALTY COMING SOON

$2,495,000

4 beds4.5 baths4,509 sq ft

1140 Oakley Ave, Winnetka, IL 60093

Home values near 255 Chestnut St

Data from public records.

Address	Redfin Estimate
220 Chestnut Street, Winnetka, IL 6 Beds \| 8 Baths \| 8986 Sq. Ft.	$4,357,526
263 Chestnut Street, Winnetka, IL 6 Beds \| 7.5 Baths \| 7500 Sq. Ft.	$4,738,924

Address	Redfin Estimate
247 Chestnut Street, Winnetka, IL 6 Beds \| 5 Baths \| 4584 Sq. Ft.	$2,753,196
277 Chestnut Street, Winnetka, IL 7 Beds \| 4.5 Baths \| 5472 Sq. Ft.	$2,794,150

Address	Redfin Estimate
240 Chestnut Street, Winnetka, IL 6 Beds \| 3.5 Baths \| 7220 Sq. Ft.	$4,731,643
260 Chestnut Street, Winnetka, IL 6 Beds \| 4.5 Baths \| 4808 Sq. Ft.	$3,005,982

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

60043 homes for sale
60022 homes for sale
60091 homes for sale
60093 homes for sale

Houses for rent in Winnetka	Agents near me	Glenview, IL homes for sale	Winnetka Housing Market
Houses for sale near me	Chicago, IL homes for sale	Evanston, IL homes for sale
Land for sale near me	Naperville, IL homes for sale	Oak Park, IL homes for sale
Open Houses near me	Schaumburg, IL homes for sale	Winnetka Property Records
Condos for sale near me	Arlington Heights, IL homes for sale	IL New Listings

Arlington Heights homes for sale
Glenview homes for sale
Chicago homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 60093, IL

Sale history for 255 Chestnut St

Tax history for 255 Chestnut St

Zoning

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 60093

Home values near 255 Chestnut St

More real estate resources