Chesham Dr, Orlando, FL Property Records

Orange County property records for 53 addresses on Chesham Dr, Orlando, FL · Last verified August 2026

Chesham Dr Highlights

Properties 53
Median Sale Price $355,000
Deeds and Mortgages on File 72
Median Price per Sqft $235
Owner Occupied 83%
Median Annual Tax Bill $3,999
Median Year Built 1987
Median Ownership Tenure 6 years

Properties on Chesham Dr

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

9912 Chesham Dr

3 bd · 2 ba · 1,676 sqft · built 1988 · 0.195 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Mar 2020 $4,4312025 Amount on Record May 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

9913 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000May 2026 $2,2952025 Amount on Record Aug 2011 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

9921 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.193 acres

Last Sale Tax Bill Prior Sale Owner Records
$232,500Jan 2020 $3,5522025 Amount on Record Jun 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

9929 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.201 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,100Feb 2016 $5,2792025 Amount on Record May 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

9930 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$389,000Nov 2022 $5,6532025 Amount on Record Feb 2021 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

9937 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$240,000Jan 2020 $3,8992025 Amount on Record Jun 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

9938 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.183 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,2102025 1 Name on Record Owner Occupied AssessorUpdated May 2026

9945 Chesham Dr

3 bd · 2 ba · 1,312 sqft · built 1987 · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,900Jul 2006 $2,1052025 Amount on Record Dec 1998 2 Names on Record Owner Occupied AssessorUpdated May 2026

9953 Chesham Dr

4 bd · 2 ba · 1,679 sqft · built 1987 · 0.186 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,700Oct 2014 $6,1752025 Amount on Record Nov 1994 2 Names on Record AssessorUpdated May 2026

9961 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.186 acres

Last Sale Tax Bill Prior Sale Owner Records
$29,400Aug 2019 $6252025 Amount on Record Dec 2014 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

9969 Chesham Dr

3 bd · 2 ba · 1,312 sqft · built 1987 · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Aug 2006 $2,2542025 2 Names on Record Owner Occupied AssessorUpdated May 2026

9977 Chesham Dr

3 bd · 2 ba · 1,706 sqft · built 1987 · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3502025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

9985 Chesham Dr

3 bd · 2 ba · 2,013 sqft · built 1987 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$155,000Oct 2019 $2,7482025 Amount on Record Aug 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

9993 Chesham Dr

3 bd · 2 ba · 1,462 sqft · built 1988 · 0.253 acres

Last Sale Tax Bill Prior Sale Owner Records
$88,500Dec 1995 $5,0012025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10001 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.285 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,5292025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

10009 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.204 acres

Last Sale Tax Bill Prior Sale Owner Records
$410,000May 2024 $5,4062025 Amount on Record May 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

10017 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,2102025 1 Name on Record Owner Occupied AssessorUpdated May 2026

10018 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1988 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Aug 2025 $2,4352025 Amount on Record May 2012 1 Name on Record Assessor + 1 DocumentUpdated May 2026

10025 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987

Last Sale Tax Bill Prior Sale Owner Records
$350,000Dec 2025 $5,8352025 Amount on Record Jul 2024 2 Names on Record Assessor + 1 DocumentUpdated May 2026

10026 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$213,500Jul 2019 $5,7472025 Amount on Record Apr 2019 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

10033 Chesham Dr

3 bd · 2 ba · 1,706 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,2132025 2 Names on Record Owner Occupied AssessorUpdated May 2026

10034 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,2942025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10041 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$278,100Jul 2021 $4,9192025 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10042 Chesham Dr

3 bd · 2 ba · 1,525 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Mar 2025 $6,0672025 Amount on Record Jan 2021 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10049 Chesham Dr

3 bd · 2 ba · 1,253 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$359,900Mar 2025 $5,1492025 Amount on Record Feb 2019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

10050 Chesham Dr

3 bd · 2 ba · 1,321 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Sep 2019 $3,6952025 Amount on Record Sep 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10057 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Mar 2026 $3,9992025 Amount on Record Jul 2008 1 Name on Record Assessor + 1 DocumentUpdated May 2026

10058 Chesham Dr

3 bd · 2 ba · 1,518 sqft · built 1987 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$57,200Dec 2016 $2,2142025 Amount on Record Feb 2007 1 Name on Record Owner Occupied AssessorUpdated May 2026

10065 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$88,000Mar 1997 $1,9972025 1 Name on Record Owner Occupied AssessorUpdated May 2026

10066 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1988 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Aug 2023 $4,8692025 Amount on Record Jun 2017 2 Names on Record Owner Occupied AssessorUpdated May 2026

10073 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Mar 2019 $4,0182025 Amount on Record Jul 2002 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

10074 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.168 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,8802025 1 Name on Record Owner Occupied AssessorUpdated May 2026

10082 Chesham Dr

3 bd · 2 ba · 1,479 sqft · built 1987 · 0.168 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Oct 2021 $4,7262025 Amount on Record Aug 2011 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10103 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Jul 2024 $5,8112025 Amount on Record Mar 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10104 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$162,000Jan 2015 $6252025 Amount on Record Mar 2012 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

10111 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,600Oct 2019 $3,8002025 —Jul 2019 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

10112 Chesham Dr

3 bd · 2 ba · 1,268 sqft · built 1987 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$241,000Feb 2021 $4,3332025 Amount on Record Jun 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

10119 Chesham Dr

3 bd · 2 ba · 1,448 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$172,000Feb 2014 $2,8502025 Amount on Record Nov 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10120 Chesham Dr

4 bd · 2 ba · 1,647 sqft · built 1987 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$158,000May 2004 $2,4042025 Amount on Record Nov 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

10127 Chesham Dr

3 bd · 2 ba · 1,805 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$311,000Dec 2019 $4,6292025 Amount on Record Aug 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

10128 Chesham Dr

3 bd · 2 ba · 1,312 sqft · built 1987 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Dec 2013 $2,6022025 Amount on Record Jun 1996 1 Name on Record Owner Occupied AssessorUpdated May 2026

10135 Chesham Dr

3 bd · 2 ba · 1,289 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Jun 2023 $5,8832025 Amount on Record Feb 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

10136 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.182 acres

Last Sale Tax Bill Prior Sale Owner Records
$318,000Dec 2021 $5,6992025 Amount on Record Apr 2013 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

10143 Chesham Dr

4 bd · 2 ba · 1,632 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Jan 2020 $4,5652025 Amount on Record Oct 2005 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10151 Chesham Dr

4 bd · 2 ba · 1,569 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000May 2011 $5,7062025 Amount on Record Nov 2010 2 Names on Record AssessorUpdated May 2026

10159 Chesham Dr

3 bd · 2 ba · 1,510 sqft · built 1987 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$355,000Jul 2026 $5,6912025 Amount on Record May 2021 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

10167 Chesham Dr

0.054 acres

Last Sale Tax Bill Prior Sale Owner Records
2 Names on Record AssessorUpdated May 2026

10205 Chesham Dr

4 bd · 2.5 ba · 2,528 sqft · built 1988 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,4062025 2 Names on Record Owner Occupied AssessorUpdated May 2026

10213 Chesham Dr

3 bd · 2 ba · 1,975 sqft · built 1987 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2021 $6012025 Amount on Record Mar 2017 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

10221 Chesham Dr

4 bd · 2 ba · 2,478 sqft · built 1987 · 0.223 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Jul 2016 $7,5452025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

10229 Chesham Dr

4 bd · 3 ba · 2,579 sqft · built 1987 · 0.223 acres

Last Sale Tax Bill Prior Sale Owner Records
$6012025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

10237 Chesham Dr

3 bd · 2 ba · 2,131 sqft · built 1987

Last Sale Tax Bill Prior Sale Owner Records
$2,9812025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

10245 Chesham Dr

4 bd · 2 ba · 2,131 sqft · built 1987 · 0.222 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Dec 2016 $4,6682025 Amount on Record Dec 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

Wildfire Risk on Chesham Dr

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

Wildfire RiskLow
this street's cells rank above 14% of the US · above 5% of Florida
Wildfire LikelihoodAbout 1 in 4,225 per year
ExposureDirect
1 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets