Windsor Dr, Oswego, IL Property Records

Kendall County property records for 46 addresses on Windsor Dr, Oswego, IL · Last verified August 2026

Windsor Dr Highlights

Properties 46
Median Sale Price $402,000
Deeds and Mortgages on File 57
Median Price per Sqft $187
Owner Occupied 91%
Median Annual Tax Bill $9,729
Median Year Built 1999
Median Ownership Tenure 16 years

Properties on Windsor Dr

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

400 Windsor Dr

4 bd · 2.5 ba · 2,894 sqft · 0.367 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jan 2016 $10,7762024 Amount on Record May 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

401 Windsor Dr

4 bd · 3.5 ba · 2,570 sqft · 0.271 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$261,000May 2015 $10,3002024 Amount on Record May 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

402 Windsor Dr

3 bd · 2 ba · 1,796 sqft · 0.301 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$289,000Jul 2004 $8,9032024 Amount on Record Mar 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

403 Windsor Dr

4 bd · 2.5 ba · 2,385 sqft · 0.266 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$314,500Aug 2004 $10,0232024 Amount on Record Aug 1999 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

404 Windsor Dr

3 bd · 2 ba · 1,801 sqft · 0.307 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jul 1999 $9,3642024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

405 Windsor Dr

4 bd · 2.5 ba · 2,452 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$223,000Aug 1999 $9,9982024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

406 Windsor Dr

3 bd · 2 ba · 2,024 sqft · 0.296 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$380,000Dec 2025 $5,9012024 Amount on Record Jun 2004 2 Names on Record Assessor + 1 DocumentUpdated Jun 2026

408 Windsor Dr

4 bd · 2.5 ba · 2,585 sqft · 0.284 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$225,000May 2000 $10,0822024 Amount on Record Aug 1999 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

410 Windsor Dr

4 bd · 2.5 ba · 2,176 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000May 2016 $9,7812024 Amount on Record Dec 2001 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

411 Windsor Dr

4 bd · 2.5 ba · 2,292 sqft · 0.254 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$203,500Sep 1997 $9,8942024 —Apr 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

412 Windsor Dr

4 bd · 2.5 ba · 2,489 sqft · 0.267 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,000May 2002 $9,8712024 Amount on Record May 2001 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

413 Windsor Dr

4 bd · 2.5 ba · 2,171 sqft · 0.256 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$495,000Oct 2024 $10,4282024 Amount on Record May 1998 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

414 Windsor Dr

2 bd · 2 ba · 1,642 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$160,500Jan 1999 $7,9262024 Amount on Record Sep 1998 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

415 Windsor Dr

4 bd · 2.5 ba · 2,113 sqft · 0.258 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Sep 2020 $9,5762024 Amount on Record Feb 2002 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

416 Windsor Dr

4 bd · 2.5 ba · 2,376 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$200,000Mar 2012 $9,5822024 Amount on Record May 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

417 Windsor Dr

4 bd · 2.5 ba · 2,373 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$198,000Jan 1998 $9,7562024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

418 Windsor Dr

4 bd · 2.5 ba · 2,287 sqft · 0.254 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$298,000Sep 2005 $9,4672024 Amount on Record Dec 1997 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

419 Windsor Dr

4 bd · 2.5 ba · 2,547 sqft · 0.256 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$219,000Jun 1999 $10,3812024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

420 Windsor Dr

3 bd · 2.5 ba · 1,696 sqft · 0.253 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000Dec 2022 $7,8812024 Amount on Record Feb 2021 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

422 Windsor Dr

3 bd · 2 ba · 1,494 sqft · 0.29 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$30,000Jul 1999 $6,7802024 Amount on Record May 1996 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

424 Windsor Dr

3 bd · 2 ba · 1,754 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$30,000Jun 1998 $8,2922024 —Jun 1998 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

426 Windsor Dr

4 bd · 2.5 ba · 2,260 sqft · 0.294 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$50,000Oct 2022 $9,4962024 Amount on Record Nov 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

428 Windsor Dr

3 bd · 2 ba · 2,515 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$400,000Apr 2025 $10,7532024 —Dec 2021 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

430 Windsor Dr

4 bd · 2.5 ba · 2,670 sqft · 0.281 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$402,000Nov 2022 $9,8742024 Amount on Record Mar 2003 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

431 Windsor Dr

4 bd · 2.5 ba · 2,514 sqft · 0.279 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$34,000Feb 1996 $10,6162024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

432 Windsor Dr

4 bd · 2.5 ba · 2,430 sqft · 0.488 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$186,000Oct 1996 $9,7172024 Amount on Record Aug 1995 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

434 Windsor Dr

4 bd · 2.5 ba · 2,018 sqft · 0.492 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$272,000Dec 2003 $9,6852024 Amount on Record Aug 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

436 Windsor Dr

4 bd · 2.5 ba · 2,188 sqft · 0.323 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$258,000Apr 2015 $9,4742024 Amount on Record Feb 2012 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

437 Windsor Dr

4 bd · 2.5 ba · 2,333 sqft · 0.268 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Oct 2009 $9,8262024 Amount on Record Apr 1996 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

438 Windsor Dr

4 bd · 2.5 ba · 2,154 sqft · 0.276 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$232,000Sep 2001 $9,1332024 Amount on Record May 1996 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

440 Windsor Dr

4 bd · 2.5 ba · 2,084 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$230,000Sep 2014 $9,4942024 Amount on Record Jun 2009 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

442 Windsor Dr

4 bd · 2.5 ba · 2,148 sqft · 0.251 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$262,000Oct 2004 $9,1992024 Amount on Record Jun 1996 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

443 Windsor Dr

4 bd · 2.5 ba · 2,435 sqft · 0.253 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$273,000Jun 2017 $9,6592024 Amount on Record May 1997 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

444 Windsor Dr

3 bd · 2.5 ba · 1,922 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$233,000Jun 2010 $8,7012024 Amount on Record May 2010 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

445 Windsor Dr

4 bd · 2.5 ba · 2,159 sqft · 0.253 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$710,000Jul 2024 $9,4532024 Amount on Record Jul 1996 2 Names on Record AssessorUpdated Jun 2026

446 Windsor Dr

4 bd · 2.5 ba · 2,145 sqft · 0.264 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$430,000Jan 2026 $9,4152024 Amount on Record Sep 1996 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

447 Windsor Dr

2 ba · 1,674 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$228,000Jun 2003 $5,9902024 Amount on Record Feb 2003 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

452 Windsor Dr

4 bd · 2.5 ba · 2,315 sqft · 0.264 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Sep 2024 $9,7292024 Amount on Record Apr 2021 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

453 Windsor Dr

4 bd · 2.5 ba · 2,937 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jun 2019 $11,1312024 Amount on Record Jan 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

454 Windsor Dr

4 bd · 2.5 ba · 2,542 sqft · 0.249 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$470,000Feb 2024 $10,4752024 Amount on Record May 2000 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

455 Windsor Dr

4 bd · 2.5 ba · 2,387 sqft · 0.243 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$490,000Aug 2023 $10,6822024 Amount on Record Feb 2018 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Aug 2026

456 Windsor Dr

4 bd · 2.5 ba · 2,568 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$329,000Dec 2020 $10,2292024 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

457 Windsor Dr

4 bd · 2.5 ba · 2,910 sqft · 0.249 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$312,000Aug 2003 $11,2122024 Amount on Record Feb 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

459 Windsor Dr

4 bd · 2.5 ba · 2,544 sqft · 0.263 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$240,000Apr 2013 $10,5002024 Amount on Record May 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

461 Windsor Dr

4 bd · 2.5 ba · 2,950 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000Nov 2001 $11,4872024 Amount on Record Mar 2001 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

463 Windsor Dr

4 bd · 2.5 ba · 2,130 sqft · 0.315 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$278,000Mar 2005 $9,7212024 Amount on Record Feb 2000 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

Property Records in Nearby Streets