1. Home
  2. Illinois
  3. Kendall County
  4. Oswego

Chesterfield Dr, Oswego, IL Property Records

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

Chesterfield Dr Highlights

Properties 29
Median Sale Price $267,000
Deeds and Mortgages on File 27
Median Price per Sqft $130
Owner Occupied 97%
Median Annual Tax Bill $9,255
Median Year Built 1992
Median Ownership Tenure 24 years

Properties on Chesterfield Dr

Owner names and exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day trial.

102 Chesterfield Dr

3 bd · 2.5 ba · 2,133 sqft · built 1992 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$229,000Jun 2016 $9,4712024 Amount on File Nov 2009 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

109 Chesterfield Dr

4 bd · 2.5 ba · 2,362 sqft · built 1998 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$214,000Oct 2019 $9,3512024 Amount on File Apr 2001 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

View Property Record

111 Chesterfield Dr

3 bd · 2 ba · 2,072 sqft · built 1997 · 0.226 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Mar 1998 $9,3522024 Amount on File Dec 1996 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

113 Chesterfield Dr

4 bd · 2.5 ba · 2,528 sqft · built 1996 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jul 2014 $9,8572024 Amount on File Aug 1996 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

114 Chesterfield Dr

4 bd · 2.5 ba · 2,217 sqft · built 1995 · 0.271 acres

Last Sale Tax Bill Prior Sale Owner Records
$267,000Oct 2014 $9,7662024 Amount on File Aug 1995 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

View Property Record

115 Chesterfield Dr

3 bd · 2 ba · 2,005 sqft · built 1995 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000Jun 2002 $9,2552024 Amount on File Sep 2000 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

View Property Record

116 Chesterfield Dr

3 bd · 2.5 ba · 1,812 sqft · built 1992 · 0.235 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,0902024 Owner on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

117 Chesterfield Dr

3 bd · 2 ba · 1,745 sqft · built 1992 · 0.334 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,800Jun 1991 $9,1102024 2 Owners on File Owner Occupied Assessor + 5 DocumentsUpdated Oct 2026

View Property Record

118 Chesterfield Dr

3 bd · 2 ba · 1,776 sqft · built 1991 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Aug 2013 $8,4882024 Amount on File Jan 1997 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

View Property Record

119 Chesterfield Dr

4 bd · 2.5 ba · 1,900 sqft · built 1993 · 0.249 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,500Sep 2021 $8,3152024 Amount on File Sep 2017 Owner on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

View Property Record

121 Chesterfield Dr

4 bd · 2 ba · 2,049 sqft · built 1991 · 0.297 acres

Last Sale Tax Bill Prior Sale Owner Records
$147,400Apr 1991 $8,5742024 2 Owners on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

123 Chesterfield Dr

4 bd · 2 ba · 2,272 sqft · built 1991 · 0.361 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,500Jul 1997 $9,5162024 Amount on File Jun 1995 Owner on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

124 Chesterfield Dr

3 bd · 2 ba · 1,741 sqft · built 1992 · 0.323 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Sep 2019 $7,9132024 Amount on File Jun 1991 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

View Property Record

126 Chesterfield Dr

3 bd · 2 ba · 1,755 sqft · built 1990 · 0.258 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,500Mar 2002 $8,5372024 Amount on File Jan 1996 2 Owners on File Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

View Property Record

128 Chesterfield Dr

2.5 ba · 2,312 sqft · built 1992 · 0.244 acres

Last Sale Tax Bill Prior Sale Owner Records
$172,700May 1992 $5,4302024 2 Owners on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

129 Chesterfield Dr

1,713 sqft · built 1992 · 0.242 acres

Last Sale Tax Bill Prior Sale Owner Records
$157,500Nov 1991 $8,2102024 —Dec 2020 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

View Property Record

130 Chesterfield Dr

4 bd · 2.5 ba · 2,178 sqft · built 1990 · 0.246 acres

Last Sale Tax Bill Prior Sale Owner Records
$281,000Aug 2006 $9,6592024 Amount on File Aug 1990 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

131 Chesterfield Dr

4 bd · 2.5 ba · 2,214 sqft · built 1991 · 0.241 acres

Last Sale Tax Bill Prior Sale Owner Records
$186,300Feb 1991 $9,6282024 2 Owners on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

132 Chesterfield Dr

3 bd · 2 ba · 1,852 sqft · built 1990 · 0.246 acres

Last Sale Tax Bill Prior Sale Owner Records
$161,500Aug 1990 $8,5672024 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

View Property Record

133 Chesterfield Dr

4 bd · 2 ba · 2,591 sqft · built 1990 · 0.292 acres

Last Sale Tax Bill Prior Sale Owner Records
$193,000Apr 1998 $10,0252024 Amount on File Jul 1990 Owner on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

134 Chesterfield Dr

4 bd · 2 ba · 2,086 sqft · built 1990 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$178,800Sep 1990 $6,9002024 Owner on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

135 Chesterfield Dr

2,436 sqft · built 1992 · 0.294 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Apr 2026 $9,4962024 Amount on File Dec 1991 2 Owners on File Assessor + 3 DocumentsUpdated Oct 2026

View Property Record

136 Chesterfield Dr

4 bd · 2.5 ba · 2,061 sqft · built 1993 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,300Jun 1992 $9,4432024 Owner on File Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

View Property Record

137 Chesterfield Dr

3 bd · 2 ba · 1,830 sqft · built 1992 · 0.293 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Dec 2017 $8,9642024 Amount on File Dec 2012 2 Owners on File Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

View Property Record

138 Chesterfield Dr

4 bd · 2.5 ba · 2,224 sqft · built 1992 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,600Oct 1991 $8,9472024 Owner on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

139 Chesterfield Dr

24.7 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

140 Chesterfield Dr

4 bd · 2.5 ba · 2,421 sqft · built 1993 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$203,200Jun 1992 $9,9182024 2 Owners on File Owner Occupied AssessorUpdated Jun 2026

View Property Record

142 Chesterfield Dr

3 bd · 2 ba · 1,705 sqft · built 1993 · 0.251 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Sep 2002 $7,7442024 Amount on File Sep 1992 2 Owners on File Owner Occupied AssessorUpdated Oct 2026

View Property Record

144 Chesterfield Dr

4 bd · 2.5 ba · 2,232 sqft · built 1994 · 0.354 acres

Last Sale Tax Bill Prior Sale Owner Records
$292,000Jan 2021 $9,4082024 Amount on File Nov 1993 2 Owners on File Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

View Property Record

Property Records in Nearby Streets