Winter Dr, Freeport, IL Property Records

Stephenson County property records for 87 addresses on Winter Dr, Freeport, IL · Last verified July 2026

Winter Dr Highlights

Properties 87
Median Sale Price $73,000
Sales Recorded 64
Median Price per Sqft $79
Owner Occupied 90%
Median Annual Tax Bill $2,161
Median Year Built 1956
Median Ownership Tenure 8 years

Properties on Winter Dr

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

1400 Winter Dr

6,400 sqft · Built 1966 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$117,000Jul 2021 $4,2212025 1 Name on Record AssessorUpdated Jul 2026

1402 Winter Dr

3 bd · 1 ba · 1,164 sqft · 0.129 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,0502025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1403 Winter Dr

3 bd · 1 ba · 884 sqft · 0.129 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$44,900Sep 2015 $1,9222025 Amount on Record Nov 2013 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1404 Winter Dr

3 bd · 1 ba · 920 sqft · 0.159 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$45,638Jun 2004 $1,1462025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1405 Winter Dr

3 bd · 1 ba · 861 sqft · 0.129 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$54,500Oct 2010 $1,3792025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1406 Winter Dr

1 bd · Built 1800 · 0.159 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$9,500Sep 2022 $6302025 Amount on Record Oct 2014 1 Name on Record AssessorUpdated Jul 2026

1407 Winter Dr

3 bd · 1 ba · 861 sqft · 0.119 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$66,000Mar 2021 $1,9262025 Amount on Record Nov 2003 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1410 Winter Dr

3 bd · 1 ba · 861 sqft · 0.166 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,5582025 1 Name on Record AssessorUpdated Jul 2026

1412 Winter Dr

3 bd · 2 ba · 1,313 sqft · 0.163 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$91,500Nov 2020 $3,8912025 Amount on Record Aug 2002 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1414 Winter Dr

2 bd · 2 ba · 1,134 sqft · 0.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$84,000Dec 2002 $3,7142025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1415 Winter Dr

3 bd · 1 ba · 832 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$47,000Jul 2015 $7702025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1416 Winter Dr

3 bd · 1 ba · 861 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$25,000Sep 2018 $2,5102025 Amount on Record Nov 2004 1 Name on Record AssessorUpdated Jul 2026

1417 Winter Dr

3 bd · 1 ba · 900 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$80,000Dec 2024 $2,6502025 Amount on Record Oct 2005 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1418 Winter Dr

3 bd · 1 ba · 861 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$46,992Aug 2013 $2,6112025 1 Name on Record AssessorUpdated Jul 2026

1419 Winter Dr

3 bd · 1 ba · 1,176 sqft · 0.159 acres

Last Sale Tax Bill Prior Sale Owner Records
$52,500Feb 2002 $2,0322025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1420 Winter Dr

3 bd · 1 ba · 942 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$31,000Mar 2018 $2,2572025 Amount on Record May 2009 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1421 Winter Dr

3 bd · 1 ba · 832 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,9772025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1422 Winter Dr

3 bd · 1.5 ba · 1,124 sqft · 0.25 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,1612025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1423 Winter Dr

3 bd · 1 ba · 861 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$50,500Sep 2018 $1,8502025 Amount on Record Mar 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1424 Winter Dr

3 bd · 1 ba · 1,141 sqft · 0.369 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$54,500Aug 2002 $2,1422025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1425 Winter Dr

3 bd · 1.5 ba · 1,006 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,0162025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1426 Winter Dr

3 bd · 1 ba · 861 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5012025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1428 Winter Dr

3 bd · 1 ba · 861 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$38,000Jul 2009 $3882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1430 Winter Dr

3 bd · 1 ba · 957 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$94,000Aug 2024 $2,2172025 Amount on Record Nov 2023 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1432 Winter Dr

3 bd · 1 ba · 832 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,2882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1434 Winter Dr

2 bd · 1 ba · 832 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$73,000Nov 2023 $1,9862025 Amount on Record Oct 2016 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1435 Winter Dr

3 bd · 1 ba · 1,053 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,000Sep 2024 $2,3732025 Amount on Record Nov 2023 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1436 Winter Dr

3 bd · 1.5 ba · 880 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$61,000Jun 2012 $2,3882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1437 Winter Dr

2 bd · 1 ba · 1,112 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$95,500Sep 2023 $2,7632025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1438 Winter Dr

3 bd · 1 ba · 920 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$41,000May 2016 $8552025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1439 Winter Dr

3 bd · 1.5 ba · 978 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$10,000Nov 2017 $2,2202025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1440 Winter Dr

2 bd · 1 ba · 848 sqft · 0.159 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$50,000Mar 2012 $2,2332025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1441 Winter Dr

1 bd · 1 ba · 768 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$60,000Oct 2007 $1,6872025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1442 Winter Dr

3 bd · 1 ba · 768 sqft · 0.165 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$30,000Apr 2022 $2,6322025 —Jul 2015 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1443 Winter Dr

2 bd · 1 ba · 832 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$69,500May 2021 $2,2892025 Amount on Record Dec 2006 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1444 Winter Dr

3 bd · 1.5 ba · 1,081 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$58,000Jan 2014 $8242025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1445 Winter Dr

3 bd · 1 ba · 768 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5452025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1447 Winter Dr

3 bd · 1 ba · 896 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$114,000Nov 2024 $1,8512025 Amount on Record Oct 2018 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1449 Winter Dr

3 bd · 1 ba · 936 sqft · 0.159 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4542025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1450 Winter Dr

2 bd · 1 ba · 768 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$63,000May 2022 $1,8902025 Amount on Record May 2005 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1452 Winter Dr

3 bd · 1.5 ba · 1,185 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5992025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1453 Winter Dr

2 bd · 1 ba · 936 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$61,000Aug 2005 $2,4512025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1454 Winter Dr

3 bd · 1 ba · 936 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$62,000Oct 2009 $1,7232025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1456 Winter Dr

3 bd · 1 ba · 936 sqft · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$5542025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1457 Winter Dr

3 bd · 1 ba · 900 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,8082025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1458 Winter Dr

3 bd · 1.5 ba · 1,112 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,3112025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1460 Winter Dr

5 bd · 2 ba · 1,080 sqft · 0.4 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$77,500Jun 2004 $3,5372025 2 Names on Record AssessorUpdated Jul 2026

1462 Winter Dr

3 bd · 1 ba · 1,340 sqft · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,800Nov 2019 $2,2232025 Amount on Record Apr 2015 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1463 Winter Dr

3 bd · 1 ba · 1,189 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$68,000Jun 2011 $2,9572025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1464 Winter Dr

3 bd · 1 ba · 1,073 sqft · 0.269 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$25,300Jun 2015 $2,3952025 Amount on Record Apr 2010 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1466 Winter Dr

3 bd · 1 ba · 936 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$50,000Mar 2016 $3,0682025 1 Name on Record AssessorUpdated Jul 2026

1467 Winter Dr

3 bd · 1.5 ba · 1,400 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$93,500Nov 2021 $2,1612025 Amount on Record Jul 2013 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1468 Winter Dr

3 bd · 1 ba · 1,388 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$97,900May 2022 $2,0332025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1469 Winter Dr

3 bd · 1 ba · 1,116 sqft · 0.139 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$7352025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1470 Winter Dr

2 bd · 1 ba · 998 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$7652025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1471 Winter Dr

4 bd · 2 ba · 1,040 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$83,500Sep 2012 $2,7112025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1472 Winter Dr

2 bd · 1 ba · 872 sqft · 0.192 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$70,000Jul 2021 $2,9522025 1 Name on Record AssessorUpdated Jul 2026

1473 Winter Dr

2 bd · 1 ba · 832 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$61,750May 2021 $1,0412025 Amount on Record Jan 2015 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1474 Winter Dr

4 bd · 2 ba · 1,628 sqft · 0.234 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,000Oct 2024 $3,1952025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1475 Winter Dr

2 bd · 1 ba · 832 sqft · 0.158 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$55,500Nov 2004 $9312025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1477 Winter Dr

3 bd · 1 ba · 1,073 sqft · 0.158 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$35,500Oct 2013 $2,6282025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1479 Winter Dr

3 bd · 2.5 ba · 1,528 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$65,500Apr 2012 $3,8902025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1480 Winter Dr

3 bd · 1.5 ba · 996 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$55,500Jun 2016 $1,3412025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1481 Winter Dr

3 bd · 1.5 ba · 1,050 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,6432025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1482 Winter Dr

3 bd · 1 ba · 960 sqft · 0.269 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,1412025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1483 Winter Dr

3 bd · 1 ba · 1,008 sqft · 0.209 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$51,000Feb 2022 $2,4502025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1484 Winter Dr

2 bd · 1 ba · 1,161 sqft · 0.279 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$54,000Jan 2009 $2,5112025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1486 Winter Dr

3 bd · 1 ba · 1,149 sqft · 0.35 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$46,000Dec 2023 $1,1732025 Amount on Record Apr 2003 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1487 Winter Dr

2 bd · 1 ba · 988 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$9092025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1488 Winter Dr

3 bd · 1 ba · 1,050 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$53,000Oct 2011 $3,4182025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1490 Winter Dr

3 bd · 1 ba · 936 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$56,000May 2009 $6192025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1492 Winter Dr

3 bd · 2 ba · 960 sqft · 0.189 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$39,000May 2018 $2,6882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1494 Winter Dr

3 bd · 1 ba · 1,120 sqft · 0.187 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$62,000Nov 2008 $1,0652025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1500 Winter Dr

2 bd · 1.5 ba · 928 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,9912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1502 Winter Dr

3 bd · 1 ba · 1,120 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,9152025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1503 Winter Dr

4 bd · 1.5 ba · 1,300 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$103,600Dec 2023 $3,0892025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1504 Winter Dr

3 bd · 1 ba · 900 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,8742025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1505 Winter Dr

3 bd · 2 ba · 974 sqft · 0.182 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$68,900Oct 2020 $2,7452025 Amount on Record Jan 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1506 Winter Dr

3 bd · 1 ba · 1,016 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$69,350Jan 2021 $1,2872025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1507 Winter Dr

3 bd · 1 ba · 900 sqft · 0.182 acres · Garage

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

1508 Winter Dr

3 bd · 1 ba · 832 sqft · 0.185 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$63,000Feb 2020 $2,2642025 Amount on Record Jun 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1509 Winter Dr

3 bd · 1 ba · 1,015 sqft · 0.182 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$71,000Nov 2020 $2,6352025 Amount on Record Jul 2004 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1510 Winter Dr

4 bd · 1.5 ba · 900 sqft · 0.173 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$40,400Sep 2007 $2,9352025 1 Name on Record AssessorUpdated Jul 2026

1511 Winter Dr

3 bd · 1 ba · 832 sqft · 0.182 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$95,000Aug 2024 $2,9162025 Amount on Record Aug 2020 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1512 Winter Dr

2 bd · 1 ba · 1,050 sqft · 0.201 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$97,500Feb 2025 $3,3532025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1513 Winter Dr

3 bd · 1 ba · 900 sqft · 0.19 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4792025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1514 Winter Dr

2 bd · 1 ba · 900 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$74,000Feb 2004 $1,5422025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

Property Records in Nearby Streets