Winchester Dr, Freeport, IL Property Records

Stephenson County property records for 48 addresses on Winchester Dr, Freeport, IL · Last verified August 2026

Winchester Dr Highlights

Properties 48
Median Sale Price $131,000
Sales Recorded 24
Median Price per Sqft $97
Owner Occupied 92%
Median Annual Tax Bill $4,704
Median Year Built 1984
Median Ownership Tenure 6 years

Properties on Winchester Dr

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

502 Winchester Dr

3 bd · 2 ba · 2,210 sqft · 0.312 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,2052025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

508 Winchester Dr

4 bd · 3 ba · 1,584 sqft · 0.246 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,1042025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

511 Winchester Dr

3 bd · 2 ba · 1,439 sqft · 0.241 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,1932025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

514 Winchester Dr

3 bd · 2 ba · 1,508 sqft · 0.232 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,2942025 1 Name on Record AssessorUpdated Jul 2026

517 Winchester Dr

4 bd · 2.5 ba · 2,082 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$110,500Sep 2005 $6,5262025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

520 Winchester Dr

3 bd · 2 ba · 1,568 sqft · 0.206 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,6222025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

525 Winchester Dr

3 bd · 2 ba · 1,434 sqft · 0.325 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$131,000Jul 2013 $5,8402025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

600 Winchester Dr

4 bd · 2.5 ba · 2,101 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,5052025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

604 Winchester Dr

3 bd · 2 ba · 1,803 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,5262025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

607 Winchester Dr

3 bd · 3 ba · 1,229 sqft · 0.22 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$110,000Sep 2020 $4,1662025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

608 Winchester Dr

4 bd · 1 ba · 1,196 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,6932025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

612 Winchester Dr

3 bd · 2.5 ba · 1,417 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$166,750May 2021 $6,0232025 Amount on Record Mar 2017 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

613 Winchester Dr

3 bd · 2 ba · 1,198 sqft · 0.22 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,6252025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

616 Winchester Dr

3 bd · 2 ba · 1,198 sqft · 0.224 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$51,000Sep 2003 $3,9772025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1801 Winchester Dr

3 bd · 2.5 ba · 1,198 sqft · 0.329 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,6982025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1802 Winchester Dr

3 bd · 2 ba · 1,082 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$99,900Aug 2023 $4,7042025 Amount on Record May 2011 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1804 Winchester Dr

2 bd · 2 ba · 1,082 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$92,500Aug 2009 $3,8932025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1806 Winchester Dr

3 bd · 2 ba · 1,082 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$77,000Apr 2011 $3,7232025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1807 Winchester Dr

3 bd · 1.5 ba · 1,125 sqft · 0.281 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$110,000Jul 2023 $4,1012025 Amount on Record Jun 2021 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1810 Winchester Dr

2 bd · 1 ba · 1,100 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$65,000Mar 2020 $3,7422025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1812 Winchester Dr

2 bd · 1 ba · 1,076 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,0232025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1813 Winchester Dr

4 bd · 3 ba · 1,198 sqft · 0.205 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$116,000Nov 2021 $4,1912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1814 Winchester Dr

2 bd · 2.5 ba · 1,100 sqft · 1.74 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,2452025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1819 Winchester Dr

4 bd · 3 ba · 1,218 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$128,250Jul 2020 $3,5262025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1825 Winchester Dr

3 bd · 2.5 ba · 1,198 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$131,000Sep 2020 $4,1912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1830 Winchester Dr

1 bd · 7,296 sqft · 0.55 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,5622025 1 Name on Record AssessorUpdated Jul 2026

1831 Winchester Dr

2 bd · 2 ba · 1,160 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$113,000Sep 2008 $3,9232025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1837 Winchester Dr

3 bd · 2 ba · 1,200 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,3662025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1843 Winchester Dr

3 bd · 1 ba · 1,104 sqft · 0.208 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2472025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1849 Winchester Dr

3 bd · 2 ba · 1,520 sqft · 0.268 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$135,000Jun 2021 $3,2952025 Amount on Record Apr 2018 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1902 Winchester Dr

3 bd · 2.5 ba · 1,596 sqft · 0.268 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$128,000Apr 2005 $4,6612025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1907 Winchester Dr

0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$5242025 1 Name on Record AssessorUpdated Jul 2026

1910 Winchester Dr

3 bd · 2 ba · 1,821 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$126,000Sep 2004 $5,7372025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1913 Winchester Dr

3 bd · 1.5 ba · 1,652 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,3832025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1916 Winchester Dr

3 bd · 2 ba · 1,536 sqft · 0.26 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,3362025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1919 Winchester Dr

3 bd · 2.5 ba · 1,500 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$185,250May 2023 $5,9612025 Amount on Record Mar 2011 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2001 Winchester Dr

3 bd · 2.5 ba · 1,690 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$92,000Jan 2013 $6,0062025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2006 Winchester Dr

3 bd · 2 ba · 1,530 sqft · 0.324 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$218,500Sep 2024 $6,0622025 Amount on Record Aug 2021 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2007 Winchester Dr

3 bd · 2.5 ba · 1,744 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$142,900Aug 2021 $5,7462025 Amount on Record Apr 2018 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2013 Winchester Dr

3 bd · 2 ba · 1,537 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,9382025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2014 Winchester Dr

3 bd · 2 ba · 1,553 sqft · 0.211 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$124,000Jun 2006 $2,3382025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2019 Winchester Dr

3 bd · 2 ba · 1,477 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,4912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2022 Winchester Dr

3 bd · 2 ba · 1,432 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,5202025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2025 Winchester Dr

3 bd · 3 ba · 1,748 sqft · 0.238 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,000Jun 2019 $7,0592025 Amount on Record May 2010 1 Name on Record AssessorUpdated Jul 2026

2026 Winchester Dr

3 bd · 3 ba · 1,464 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,8812025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2031 Winchester Dr

3 bd · 2.5 ba · 2,498 sqft · 0.261 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$6,2082025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2034 Winchester Dr

3 bd · 2 ba · 1,468 sqft · 0.306 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,3252025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2041 Winchester Dr

4 bd · 3 ba · 1,584 sqft · 0.37 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$127,000Nov 2016 $6,1142025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

Property Records in Nearby Streets