Off Market12127d on market

255 Chestnut St

Winnetka, IL, 60093 • 60093 • Cook County

$1,229,200

$574/sqft

4Beds

2.5Baths

2,140Sqft

0.28 acLot

1954Built

Market activity

Demand and pricing signals for this listing

5 views

People checking out this listing

12127 days on market

Established listing

$574/sqft

Price per square foot

About this home

Single Family · Built 1954

This 2140 square foot single family home has 4 bedrooms and 2.5 bathrooms. This home is located at 255 Chestnut St, Winnetka, IL 60093.

Estimated monthly payment

Based on current rates

$8,017/month

Principal & Interest$6,378

Property Tax$1,229

Insurance$410

Down payment20% ($245,840)

3%50%

Est. 6.75% rate · 30yr fixed · $983,360 loan

Full calculator →

At a glance

Key facts and listing details

TypeSingleFamily

Year Built1954

CoolingNone

ParkingGarage - Attached

Lot0.28 Acres

Property

Home typeSingle Family

Year built1954

Systems

CoolingNone

RoofShake / Shingle

Parking & Outdoor

ParkingGarage - Attached

Lot0.28 Acres

Location & Tax

Neighborhood60093

Annual tax$20,240

Parcel0520405029

Features & details

3 categories of property features

Interior Features

Cooling

None

Exterior Features

Exterior

Stone

Parking

Garage - Attached

Listing insights

Market data and value estimates

StatusOff Market

Days on market12127

Est. value$1,229,200

Est. rent$5,838/mo

Tax rate1.99%

Price/sqft$574

Last sold$505,000

Tour days6

How are the schools in Winnetka?

3 schools rated nearby

Crow Island Elementary School

Elementary • Public • K-4

0.6 mi

Carleton W Washburne School

Middle • Public • 7-8

1.0 mi

New Trier Township High School Winnetka

High • Public • 10-12

0.9 mi

Location

Winnetka, IL, 60093

Expand map

Price history

1 event

DateEventPrice$/sqftSource

Jan 25, 1993Sold$505,000$236Agent Provided

Sold$505,000

Jan 25, 1993•$236/sqft•Agent Provided

Tax history

25 years of records

YearTax paidAssessed value

Apr 10, 2023$20,240$90,621

Apr 10, 2022$20,675$98,148

Apr 10, 2021$14,847$60,541

Apr 10, 2020$14,669$60,541

Apr 10, 2019$14,546$65,806

Apr 10, 2018$18,044$78,662

Apr 10, 2017$18,490$82,920

Apr 10, 2016$17,805$82,920

Apr 10, 2015$16,087$68,009

Apr 10, 2014$15,755$68,009

Apr 10, 2013$15,013$68,009

Apr 10, 2012$17,290$81,584

Apr 10, 2011$16,561$81,584

Apr 10, 2010$15,243$81,584

Apr 10, 2009$15,132$92,663

Apr 10, 2008$14,137$97,541

Apr 10, 2007$13,190$97,541

Apr 10, 2006$13,878$83,525

Apr 10, 2005$13,639$83,525

Apr 10, 2004$13,148$83,525

Apr 10, 2003$11,769$61,576

Apr 10, 2002$10,910$61,576

Apr 10, 2001$9,732$61,576

Apr 10, 2000$9,449$52,288

Apr 10, 1999$8,789$52,288

Nearby homes

Off Market

$3,987,000

6 bd8 ba7,500 sqft

263 Chestnut St, Winnetka, IL

Off Market

$2,346,800

6 bd5 ba4,584 sqft

247 Chestnut St, Winnetka, IL

Off Market

$1,437,300

4 bd3 ba2,620 sqft

269 Chestnut St, Winnetka, IL

Off Market

$3,030,000

7 bd4.5 ba7,020 sqft

266 Linden St, Winnetka, IL

Off Market

$5,000

4 bd2.5 ba

266 Linden St, Winnetka, IL

Off Market

$2,589,300

5 bd6 ba5,000 sqft

811 Sunset Rd, Winnetka, IL

Off Market

$4,150,700

5 bd7 ba7,000 sqft

260 Linden St, Winnetka, IL

Off Market

$2,928,800

6 bd4.5 ba5,472 sqft

277 Chestnut St, Winnetka, IL

Neighborhood details

Local context around this listing

Winnetka, IL • Cook County

Nearby cities

Arlington HeightsChicagoCiceroDes PlainesElginEvanstonOrland ParkPalatine

Nearby zip codes

60093

Similar homes

For Sale

$1,249,000

4 bd3 ba2,708 sqft

1975 Valley View Rd, Northfield, IL

For Sale

$950,000

4 bd2 ba2,100 sqft

979 Vine St, Winnetka, IL

For Sale

$1,399,000

4 bd4 ba2,455 sqft

526 Isabella St, Wilmette, IL

For Sale

$995,000

3 bd2 ba2,642 sqft

1917 Greenwood Ave, Wilmette, IL

For Sale

4 bd3 ba2,273 sqft

412 Ashland Ave, Evanston, IL

For Sale

4 bd3 ba2,640 sqft

2250 N Western Ave, Park Ridge, IL

For Sale

$1,500,000

4 bd4 ba3,200 sqft

90 Linden Ave, Glencoe, IL

For Sale

$950,000

4 bd3 ba2,551 sqft

2729 Lawndale Ave, Evanston, IL

For Sale

$1,025,000

4 bd4 ba3,000 sqft

900 Stonegate Dr, Highland Park, IL

For Sale

4 bd3 ba2,313 sqft

6219 N Saint Louis Ave, Chicago, IL

For Sale

$969,000

4 bd3 ba2,000 sqft

2319 Asbury Ave, Evanston, IL

For Sale

$824,499

4 bd3 ba3,000 sqft

3336 Overland Pass, Northbrook, IL

For Sale

$749,000

4 bd2 ba2,803 sqft

1809 Jefferson Ave, Glenview, IL

For Sale

$899,900

4 bd4 ba3,000 sqft

610 Revere Rd, Glenview, IL

For Sale

$849,900

4 bd3 ba2,310 sqft

3122 Sandy Ln, Glenview, IL

For Sale

$1,000,000

4 bd4 ba2,589 sqft

323 N Prospect Ave, Park Ridge, IL

For Sale

$839,999

4 bd3 ba1,424 sqft

3134 Maple Leaf Dr, Glenview, IL

For Sale

$699,000

4 bd3 ba2,336 sqft

3035 Rennes Ct, Northbrook, IL

For Sale

$1,249,000

3 bd3 ba1,500 sqft

2415 Lake Ave, Wilmette, IL

For Sale

$825,000

4 bd3 ba2,633 sqft

805 Sutton Dr, Northbrook, IL

Tour This Home

Pick a date

Preferred time

Apr 10, 2026

No obligation · Same-day confirmation · Takes 30 seconds

Need a different time? Request custom scheduling

Have a Question?

Get details on this property, the neighborhood, or the buying process.

Ask About This Property

We typically respond within a few hours

Download property brochure

Photos, details & neighborhood info in one PDF

Get brochure

Free · No sign-up required

Get pre-approved

Know your budget & strengthen your offer

Check eligibility

Value estimates

Live

Est. value$1,229,200

Est. rent$5,838/mo

Affordability$8,426/mo

Own a home nearby?

See what it's worth in today's market

Get estimate

Schedule Tour Ask

No obligation · Same-day response