Winthrop Dr, Oswego, IL Property Records

Kendall County property records for 29 addresses on Winthrop Dr, Oswego, IL · Last verified August 2026

Winthrop Dr Highlights

Properties 29
Median Sale Price $532,000
Deeds and Mortgages on File 54
Median Price per Sqft $142
Owner Occupied 100%
Median Annual Tax Bill $12,055
Median Year Built 2014
Median Ownership Tenure 11 years

Properties on Winthrop Dr

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

300 Winthrop Dr

4 bd · 2.5 ba · 3,316 sqft · built 2016 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$547,500Jul 2026 $12,0492025 Amount on Record May 2022 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

301 Winthrop Dr

4 bd · 3.5 ba · 3,829 sqft · built 2011 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$540,000Oct 2023 $13,1692024 Amount on Record Mar 2018 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Jun 2026

302 Winthrop Dr

4 bd · 2.5 ba · 2,821 sqft · built 2016 · 0.283 acres

Last Sale Tax Bill Prior Sale Owner Records
$406,000Mar 2022 $11,5472024 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

303 Winthrop Dr

4 bd · 2.5 ba · 2,794 sqft · built 2014 · 0.272 acres

Last Sale Tax Bill Prior Sale Owner Records
$304,500Oct 2014 $11,7132024 Amount on Record Sep 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

304 Winthrop Dr

4 bd · 2.5 ba · 2,498 sqft · built 2014 · 0.287 acres

Last Sale Tax Bill Prior Sale Owner Records
$301,000Jan 2017 $10,7332024 Amount on Record Feb 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

305 Winthrop Dr

4 bd · 3 ba · 3,718 sqft · built 2007 · 0.312 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Jun 2007 $12,4092024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

306 Winthrop Dr

4 bd · 2.5 ba · 3,316 sqft · built 2014 · 0.284 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Sep 2014 $12,3852024 Amount on Record Jun 2013 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

308 Winthrop Dr

4 bd · 2.5 ba · 2,806 sqft · built 2014 · 0.272 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000May 2017 $12,3172024 Amount on Record Apr 2014 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

309 Winthrop Dr

5 bd · 3 ba · 3,829 sqft · built 2009 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Dec 2020 $12,3682024 Amount on Record Jun 2011 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

310 Winthrop Dr

4 bd · 2.5 ba · 2,811 sqft · built 2014 · 0.278 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000May 2014 $12,1732024 Amount on Record Nov 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

311 Winthrop Dr

4 bd · 2.5 ba · 2,798 sqft · built 2014 · 0.278 acres

Last Sale Tax Bill Prior Sale Owner Records
$373,000Apr 2014 $12,4782024 Amount on Record Sep 2013 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

312 Winthrop Dr

4 bd · 2.5 ba · 2,785 sqft · built 2014 · 0.273 acres

Last Sale Tax Bill Prior Sale Owner Records
$324,500May 2014 Amount on Record Sep 2013 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

313 Winthrop Dr

4 bd · 2.5 ba · 2,662 sqft · built 2010 · 0.291 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,000Jan 2011 $10,1372024 Amount on Record Nov 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

314 Winthrop Dr

4 bd · 2.5 ba · 3,172 sqft · built 2014 · 0.273 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Jul 2020 $12,5272024 Amount on Record Jul 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

315 Winthrop Dr

4 bd · 2.5 ba · 2,782 sqft · built 2014 · 0.295 acres

Last Sale Tax Bill Prior Sale Owner Records
$295,500May 2014 $11,6792024 Amount on Record Jun 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

316 Winthrop Dr

4 bd · 2.5 ba · 2,821 sqft · built 2015 · 0.274 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,000Apr 2017 $12,1072024 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

317 Winthrop Dr

3 bd · 2 ba · 2,461 sqft · built 2007 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Mar 2013 $9,5672024 Amount on Record Oct 2012 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

318 Winthrop Dr

3 bd · 2.5 ba · 2,998 sqft · built 2014 · 0.279 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,500Sep 2014 $12,5822024 Amount on Record Jan 2014 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

319 Winthrop Dr

4 bd · 2.5 ba · 3,336 sqft · built 2007 · 0.291 acres

Last Sale Tax Bill Prior Sale Owner Records
$382,000Aug 2007 $12,0062024 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

320 Winthrop Dr

4 bd · 2.5 ba · 2,770 sqft · built 2015 · 0.277 acres

Last Sale Tax Bill Prior Sale Owner Records
$554,000Aug 2024 $12,0552024 Amount on Record Apr 2019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

321 Winthrop Dr

4 bd · 2.5 ba · 3,735 sqft · built 2007 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$532,000Jun 2023 $12,3472024 Amount on Record Jun 2007 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

322 Winthrop Dr

5 bd · 2.5 ba · 2,811 sqft · built 2015 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$322,500Apr 2015 $11,5562024 Amount on Record Mar 2015 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

323 Winthrop Dr

4 bd · 2.5 ba · 2,308 sqft · built 2016 · 0.288 acres

Last Sale Tax Bill Prior Sale Owner Records
$278,000Jan 2018 $10,5072024 Amount on Record May 2016 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

324 Winthrop Dr

3 bd · 2.5 ba · 2,788 sqft · built 2016 · 0.282 acres

Last Sale Tax Bill Prior Sale Owner Records
$303,000Jun 2016 $11,9272024 Amount on Record Jan 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

326 Winthrop Dr

4 bd · 2.5 ba · 2,821 sqft · built 2015 · 0.282 acres

Last Sale Tax Bill Prior Sale Owner Records
$282,000Jul 2015 $12,0142024 Amount on Record Apr 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

328 Winthrop Dr

4 bd · 2.5 ba · 2,795 sqft · built 2015 · 0.285 acres

Last Sale Tax Bill Prior Sale Owner Records
$306,000May 2015 $12,1832024 Amount on Record Apr 2014 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

330 Winthrop Dr

4 bd · 2.5 ba · 2,785 sqft · built 2015 · 0.278 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jun 2015 $12,3412024 Amount on Record Oct 2014 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

332 Winthrop Dr

4 bd · 2.5 ba · 2,847 sqft · built 2015 · 0.29 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Jun 2015 $11,7142024 Amount on Record Oct 2014 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

334 Winthrop Dr

4 bd · 2.5 ba · 3,012 sqft · built 2016 · 0.336 acres

Last Sale Tax Bill Prior Sale Owner Records
$327,000Feb 2016 $11,7762024 Amount on Record May 2015 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

Wildfire Risk on Winthrop Dr

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

Property Records in Nearby Streets