Middlebury Rd, Freeport, IL Property Records

Stephenson County property records for 56 addresses on Middlebury Rd, Freeport, IL · Last verified July 2026

Middlebury Rd Highlights

Properties 56
Median Sale Price $87,500
Sales Recorded 33
Median Price per Sqft $79
Owner Occupied 100%
Median Annual Tax Bill $3,706
Median Year Built 1968
Median Ownership Tenure 8 years

Properties on Middlebury Rd

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

1805 Middlebury Rd

3 bd · 1.5 ba · 1,028 sqft · 0.279 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,4382025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1809 Middlebury Rd

3 bd · 2 ba · 1,374 sqft · 0.2 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,3072025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1815 Middlebury Rd

3 bd · 2 ba · 1,584 sqft · 0.369 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$85,000Jul 2015 $3,9672025 Amount on Record May 2005 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1821 Middlebury Rd

3 bd · 1.5 ba · 1,266 sqft · 0.4 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$141,000May 2024 $3,6942025 Amount on Record Apr 2020 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1827 Middlebury Rd

3 bd · 2 ba · 1,323 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100,800Mar 2022 $3,3912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1831 Middlebury Rd

3 bd · 2 ba · 1,028 sqft · 0.309 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$81,000Aug 2004 $3,4622025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1834 Middlebury Rd

3 bd · 1.5 ba · 1,323 sqft · 0.219 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$87,500Mar 2021 $3,4032025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1837 Middlebury Rd

3 bd · 1.5 ba · 1,614 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$85,000Aug 2017 $3,5152025 Amount on Record May 2006 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1841 Middlebury Rd

3 bd · 2 ba · 1,106 sqft · 0.277 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,7562025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1842 Middlebury Rd

3 bd · 1.5 ba · 1,701 sqft · 0.229 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,8962025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1849 Middlebury Rd

4 bd · 2 ba · 1,118 sqft · 0.277 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$75,000Sep 2020 $3,8022025 Amount on Record Jun 2010 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1850 Middlebury Rd

3 bd · 2 ba · 1,118 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$87,500Jun 2021 $3,7062025 Amount on Record Jun 2012 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1856 Middlebury Rd

3 bd · 2 ba · 1,080 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,7162025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1857 Middlebury Rd

3 bd · 2 ba · 1,118 sqft · 0.32 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,7082025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1863 Middlebury Rd

3 bd · 2.5 ba · 1,419 sqft · 0.399 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$117,000Jul 2004 $3,8402025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1864 Middlebury Rd

3 bd · 1 ba · 1,294 sqft · 0.25 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2932025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1908 Middlebury Rd

3 bd · 3 ba · 1,324 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$104,900May 2020 $4,3712025 Amount on Record Apr 2013 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1909 Middlebury Rd

4 bd · 3 ba · 1,352 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$114,400Jul 2018 $4,4722025 Amount on Record Nov 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1915 Middlebury Rd

3 bd · 2.5 ba · 1,080 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$120,000Jan 2022 $3,7892025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1916 Middlebury Rd

3 bd · 1.5 ba · 1,248 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,1362025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1923 Middlebury Rd

4 bd · 2.5 ba · 1,764 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$85,000Sep 2022 $4,5032025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1924 Middlebury Rd

4 bd · 3 ba · 1,108 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$173,000Oct 2024 $4,1742025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1931 Middlebury Rd

3 bd · 2 ba · 1,080 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$85,900Oct 2020 $3,7302025 Amount on Record Aug 2017 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1932 Middlebury Rd

4 bd · 2 ba · 1,080 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,2302025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1939 Middlebury Rd

4 bd · 2.5 ba · 1,761 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$108,500Oct 2007 $4,4882025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1940 Middlebury Rd

4 bd · 2 ba · 1,617 sqft · 0.269 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,000Jul 2013 $4,6502025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1945 Middlebury Rd

4 bd · 2 ba · 1,080 sqft · 0.239 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$94,905Jun 2021 $3,7192025 Amount on Record Apr 2010 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1946 Middlebury Rd

3 bd · 2 ba · 1,272 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$78,000May 2004 $3,7582025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

1953 Middlebury Rd

4 bd · 2.5 ba · 1,620 sqft · 0.259 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,2272025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

1954 Middlebury Rd

4 bd · 3.5 ba · 1,836 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,000Jan 2002 $4,7842025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2001 Middlebury Rd

3 bd · 1.5 ba · 1,080 sqft · 0.293 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4562025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2006 Middlebury Rd

3 bd · 2 ba · 1,092 sqft · 0.329 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$97,000Feb 2013 $4,1612025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2007 Middlebury Rd

3 bd · 2.5 ba · 1,576 sqft · 0.293 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$123,000Mar 2011 $5,0562025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2015 Middlebury Rd

3 bd · 2 ba · 1,102 sqft · 0.293 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,7542025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2016 Middlebury Rd

3 bd · 1.5 ba · 1,232 sqft · 0.37 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,0962025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2019 Middlebury Rd

4 bd · 2.5 ba · 1,620 sqft · 0.293 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$71,154Nov 2011 $3,9812025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2031 Middlebury Rd

3 bd · 1.5 ba · 1,080 sqft · 0.331 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$84,000Mar 2017 $3,8622025 Amount on Record Mar 2005 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2100 Middlebury Rd

3 bd · 1.5 ba · 1,443 sqft · 0.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,2422025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2101 Middlebury Rd

4 bd · 2 ba · 768 sqft · 0.367 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$58,000Jan 2025 $3,5912025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2104 Middlebury Rd

5 bd · 1.5 ba · 1,140 sqft · 0.295 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,1772025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2105 Middlebury Rd

3 bd · 1.5 ba · 936 sqft · 0.331 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2022025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2108 Middlebury Rd

3 bd · 2 ba · 1,341 sqft · 0.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,7082025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2109 Middlebury Rd

3 bd · 2 ba · 1,151 sqft · 0.329 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,3552025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2111 Middlebury Rd

3 bd · 1.5 ba · 976 sqft · 0.35 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$86,500Mar 2017 $3,0042025 Amount on Record Jun 2013 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2112 Middlebury Rd

3 bd · 2.5 ba · 1,134 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,6902025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2115 Middlebury Rd

3 bd · 1.5 ba · 984 sqft · 0.369 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$62,000Aug 2015 $3,1612025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2116 Middlebury Rd

3 bd · 1.5 ba · 1,080 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,2742025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2120 Middlebury Rd

3 bd · 2 ba · 976 sqft · 0.35 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$83,400Nov 2020 $3,4732025 Amount on Record Jan 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2124 Middlebury Rd

3 bd · 1 ba · 976 sqft · 0.389 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$95,500Oct 2009 $3,4092025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2128 Middlebury Rd

3 bd · 1 ba · 976 sqft · 0.339 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$88,990Aug 2019 $3,3552025 Amount on Record Oct 2007 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2129 Middlebury Rd

3 bd · 1.5 ba · 976 sqft · 0.329 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$63,000Jan 2019 $3,4212025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2132 Middlebury Rd

3 bd · 1.5 ba · 976 sqft · 0.4 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$67,000Dec 2014 $3,4072025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2133 Middlebury Rd

3 bd · 1 ba · 1,152 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,5792025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

2136 Middlebury Rd

4 bd · 1.5 ba · 768 sqft · 0.439 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$86,500Oct 2019 $2,9062025 Amount on Record Sep 2008 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2137 Middlebury Rd

3 bd · 1.5 ba · 1,104 sqft · 0.319 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$4,0292025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

2140 Middlebury Rd

3 bd · 1.5 ba · 1,372 sqft · 0.369 acres · Garage

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

Wildfire Risk on Middlebury Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank at the 2nd percentile of exposed land nationally · 15th in Illinois
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
2 of 4 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets