Cook County property records for 12 addresses on Oakley Ave, Winnetka, IL · Last verified August 2026
| Properties | 12 |
|---|---|
| Median Sale Price | $1,325,000 |
| Deeds and Mortgages on File | 21 |
| Median Price per Sqft | $306 |
| Owner Occupied | 100% |
| Median Annual Tax Bill | $29,211 |
| Median Year Built | 1919 |
| Median Ownership Tenure | 7 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
6 bd · 3.5 ba · 4,728 sqft · built 1913 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,175,000Dec 2022 | $28,0522023 | Amount on Record May 1999 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jun 2026 |
6 bd · 3.5 ba · 3,823 sqft · built 1938 · 0.273 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,650,000Jul 2021 | $29,2112023 | Amount on Record Sep 2014 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Aug 2026 |
6 bd · 3.5 ba · 5,440 sqft · built 1911 · 0.369 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,435,000Nov 2018 | $44,2072023 | —Mar 2018 | Owner on Record Owner Occupied | Assessor + 5 DocumentsUpdated Jul 2026 |
6 bd · 4.5 ba · 3,987 sqft · built 1919 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,672,500Jun 2014 | $28,9092023 | Amount on Record Sep 1997 | Owner on Record Owner Occupied | AssessorUpdated Jun 2026 |
4 bd · 2.5 ba · 4,174 sqft · built 1916 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,275,000Sep 2016 | $27,5882023 | —Oct 2002 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jun 2026 |
6 bd · 3 ba · 4,353 sqft · built 1911 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $29,6202023 | Owner on Record Owner Occupied | AssessorUpdated Jun 2026 |
4 bd · 5 ba · 4,589 sqft · built 1938 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $2,400,000Jun 2025 | $35,7652023 | Amount on Record Jul 2016 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |
6 bd · 3.5 ba · 4,470 sqft · built 1922 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,615,000Aug 2010 | $35,0072023 | Amount on Record Aug 2000 | Owner on Record Owner Occupied | AssessorUpdated Jun 2026 |
5 bd · 2.5 ba · 3,757 sqft · built 1920 · 0.385 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $861,500Sep 2020 | $27,7432023 | —Sep 1996 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
5 bd · 4 ba · 3,892 sqft · built 1916 · 0.321 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,412,500Jan 2004 | $26,7522023 | —Jan 2004 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Jun 2026 |
6 bd · 4.5 ba · 3,826 sqft · built 1908 · 0.319 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,172,000Jul 2019 | $26,4022023 | Amount on Record Apr 2009 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Jun 2026 |
5 bd · 4 ba · 3,076 sqft · built 1922 · 0.255 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,325,000Jun 2021 | $29,4432023 | Amount on Record Aug 2012 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Jun 2026 |