Chestnut St, Winnetka, IL Property Records

Cook County property records for 56 addresses on Chestnut St, Winnetka, IL · Last verified August 2026

Chestnut St Highlights

Properties 56
Median Sale Price $1,450,000
Deeds and Mortgages on File 82
Median Price per Sqft $467
Owner Occupied 86%
Median Annual Tax Bill $33,391
Median Year Built 1951
Median Ownership Tenure 9 years

Properties on Chestnut St

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

126 Chestnut St

5 bd · 2.5 ba · 3,541 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,450,000Nov 2010 $29,3612023 —May 2004 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

133 Chestnut St

4 bd · 3.5 ba · 4,212 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Apr 1991 $33,3842023 1 Name on Record AssessorUpdated Jul 2026

136 Chestnut St

6 bd · 5 ba · 5,022 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$685,000Aug 1991 $41,2732023 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

146 Chestnut St

5 bd · 4.5 ba · 5,482 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Oct 2020 $41,1632023 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

147 Chestnut St

5 bd · 4.5 ba · 3,968 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,790,000Jul 2011 $32,8472023 Amount on Record Sep 2005 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

150 Chestnut St

0.565 acres

Last Sale Tax Bill Prior Sale Owner Records
—Owner Occupied AssessorUpdated Apr 2024

155 Chestnut St

5 bd · 3.5 ba · 4,077 sqft · 0.567 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$750,666Aug 1997 $37,7892023 Amount on Record Dec 1995 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

156 Chestnut St

4 bd · 3.5 ba · 3,958 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,425,000Jul 2019 $31,8712023 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

175 Chestnut St

4 bd · 3 ba · 2,494 sqft · 0.559 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,400,000May 2008 $29,2142023 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

180 Chestnut St

8 bd · 4.5 ba · 6,564 sqft · 0.55 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$950,000Sep 1997 $51,3942023 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

185 Chestnut St

5 bd · 4.5 ba · 4,776 sqft · 0.412 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,370,000Oct 2015 $33,7752023 Amount on Record Jun 2000 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

190 Chestnut St

4 bd · 2 ba · 2,452 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,307,000Nov 2022 $20,2212023 Amount on Record Apr 2018 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jun 2026

193 Chestnut St

7 bd · 8 ba · 4,977 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,905,500Jan 2016 $58,3182023 Amount on Record Dec 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

200 Chestnut St

4 bd · 3.5 ba · 4,710 sqft · 0.384 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000May 2018 $49,7712023 Amount on Record Oct 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

205 Chestnut St

6 bd · 5.5 ba · 5,604 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,775,000Dec 2022 $30,6022023 Amount on Record Aug 2022 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

206 Chestnut St

3 bd · 2.5 ba · 1,652 sqft · 0.216 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$515,000Feb 1993 $17,0822023 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

220 Chestnut St

5 bd · 6 ba · 5,265 sqft · 0.476 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,999,000Apr 2007 $59,7402023 Amount on Record Jul 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

240 Chestnut St

6 bd · 3.5 ba · 7,220 sqft · 1.01 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,525,000Aug 1999 $57,1892023 Amount on Record Mar 1995 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

247 Chestnut St

6 bd · 4.5 ba · 4,584 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,570,000Jun 2021 $35,5762023 Amount on Record May 2007 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

255 Chestnut St

4 bd · 2.5 ba · 2,140 sqft · 0.278 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$505,000Jan 1993 $20,2402023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

260 Chestnut St

6 bd · 4.5 ba · 4,808 sqft · 0.504 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,450,000Sep 2021 $44,1962023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

263 Chestnut St

6 bd · 6.5 ba · 5,019 sqft · 0.303 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,995,000Apr 2021 $68,6222023 Amount on Record Dec 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

269 Chestnut St

5 bd · 2.5 ba · 2,620 sqft · 0.244 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$980,000Apr 2022 $21,3272023 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

277 Chestnut St

7 bd · 4.5 ba · 5,472 sqft · 0.321 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,600,000Nov 2005 $43,5842023 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

312 Chestnut St

4 bd · 5 ba · 4,156 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,365,000Sep 2019 $35,8612023 Amount on Record Nov 1994 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

321 Chestnut St

4 bd · 2.5 ba · 4,206 sqft · 0.262 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Jan 2006 $41,3332023 Amount on Record May 2005 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

322 Chestnut St

6 bd · 5.5 ba · 5,057 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,410,000Jul 2019 $54,8712023 Amount on Record Jun 2016 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

329 Chestnut St

8 bd · 4.5 ba · 6,964 sqft · 0.558 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,450,000Mar 2019 $42,1202023 Amount on Record Jul 1994 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

334 Chestnut St

5 bd · 4.5 ba · 4,326 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$18,615Jan 2012 $38,3792023 —Jul 2011 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

342 Chestnut St

4 bd · 5.5 ba · 4,612 sqft · 0.429 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,150,000Dec 2020 $40,1932023 Amount on Record May 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

343 Chestnut St

4 bd · 3.5 ba · 3,840 sqft · 0.321 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Dec 2014 $33,3912023 Amount on Record Jun 2008 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

352 Chestnut St

4 bd · 2.5 ba · 2,984 sqft · 0.403 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,225,000Jul 2020 $27,0022023 Amount on Record Sep 2001 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

365 Chestnut St

6 bd · 4 ba · 3,041 sqft · 0.334 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,307,500Aug 2020 $27,9822023 Amount on Record Dec 2016 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

370 Chestnut St

5 bd · 4.5 ba · 4,392 sqft · 0.742 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,145,000Jun 1995 $43,9012023 —Oct 1993 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

375 Chestnut St

6 bd · 5 ba · 4,808 sqft · 0.654 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,900,000Jan 2004 $41,4002023 —Jan 2004 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

388 Chestnut St

5 bd · 3 ba · 2,870 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,029,000Sep 2020 $23,5652023 —Jun 1999 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

394 Chestnut St

4 bd · 2.5 ba · 3,068 sqft · 0.199 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,600,000Aug 2021 $29,1102023 Amount on Record Apr 2010 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

419 Chestnut St

3 bd · 3.5 ba · 3,514 sqft · 0.214 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,615,000Aug 2015 $31,4562023 Amount on Record Jan 2000 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

425 Chestnut St

5 bd · 3.5 ba · 1,612 sqft · 0.21 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,050,000Jul 2022 $16,4602023 Amount on Record Aug 2015 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

428 Chestnut St

4 bd · 2 ba · 1,488 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$485,000Jul 2012 $14,0692023 Amount on Record Sep 2004 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

429 Chestnut St

6 bd · 5.5 ba · 3,366 sqft · 0.214 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Jul 2013 $31,6122023 Amount on Record Mar 2004 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

437 Chestnut St

5 bd · 5.5 ba · 3,513 sqft · 0.321 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,252,000Jul 2021 $40,8232023 Amount on Record Oct 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

443 Chestnut St

5 bd · 3.5 ba · 3,248 sqft · 0.214 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Dec 2023 $30,2972023 Amount on Record Sep 2019 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jun 2026

455 Chestnut St

4 bd · 2.5 ba · 2,783 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,300,500Sep 2022 $21,0972023 Amount on Record Aug 2013 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

462 Chestnut St

3 bd · 3.5 ba · 2,444 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$850,000Aug 2013 $23,0462023 Amount on Record Jul 2009 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

466 Chestnut St

4 bd · 3.5 ba · 2,831 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,350,000Oct 2025 $1,8132023 Amount on Record Aug 2023 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

470 Chestnut St

3 bd · 1.5 ba · 1,496 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$13,4542023 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

474 Chestnut St

3 bd · 2 ba · 1,072 sqft · 0.172 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$625,000Jul 2023 $13,6582023 —May 2005 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

501 Chestnut St

Built 1927 · 0.053 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,995,000Feb 2017 $19,5842023 1 Name on Record Assessor + 2 DocumentsUpdated Jun 2026

511 Chestnut St

0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
—Owner Occupied AssessorUpdated Apr 2024

512 Chestnut St

Built 1963 · 0.693 acres

Last Sale Tax Bill Prior Sale Owner Records
—Owner Occupied AssessorUpdated Apr 2024

525 Chestnut St

1 bd · 2.5 ba · 1,272 sqft · 0.017 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Dec 2018 $9,4642023 Amount on Record Nov 2003 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

551 Chestnut St

4,000 sqft · Built 1971 · 0.116 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Mar 2018 $60,2682023 Amount on Record Aug 2001 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

555 Chestnut St

7,414 sqft · Built 1916 · 0.181 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jul 1994 $80,6332023 —Nov 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

560 Chestnut St

0.491 acres

Last Sale Tax Bill Prior Sale Owner Records
—Owner Occupied AssessorUpdated Apr 2024

566 Chestnut St

15,770 sqft · Built 1948 · 0.385 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,600,000Feb 2005 $253,8392023 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

Wildfire Risk on Chestnut St

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach of burnable land

Property Records in Nearby Streets