Headlee Dr, Orlando, FL Property Records

Orange County property records for 36 addresses on Headlee Dr, Orlando, FL · Last verified August 2026

Headlee Dr Highlights

Properties 36
Median Sale Price $280,000
Deeds and Mortgages on File 28
Median Price per Sqft $231
Owner Occupied 78%
Median Annual Tax Bill $2,638
Median Year Built 1972
Median Ownership Tenure 13 years

Properties on Headlee Dr

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

4806 Headlee Dr

3 bd · 1.5 ba · 1,020 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jan 2022 $5,2132025 Amount on Record Jun 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

4814 Headlee Dr

2 bd · 1.5 ba · 984 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$9382025 1 Name on Record Owner Occupied AssessorUpdated May 2026

4822 Headlee Dr

3 bd · 1.5 ba · 1,400 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$55,500Nov 2007 $9172025 Amount on Record May 1996 2 Names on Record Owner Occupied AssessorUpdated May 2026

4823 Headlee Dr

4 bd · 1.5 ba · 1,520 sqft · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$8112025 1 Name on Record Owner Occupied AssessorUpdated May 2026

4826 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$199,000Apr 2006 $8532025 Amount on Record Sep 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

4831 Headlee Dr

3 bd · 2 ba · 1,210 sqft · 0.167 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,800Dec 2017 $3,8562025 Amount on Record Oct 2017 2 Names on Record Assessor + 4 DocumentsUpdated May 2026

4832 Headlee Dr

2 bd · 1.5 ba · 984 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$40,000Nov 2010 $3,2572025 —May 2010 1 Name on Record AssessorUpdated May 2026

4836 Headlee Dr

4 bd · 1.5 ba · 1,212 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$167,000Feb 2018 $4,0102025 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

4839 Headlee Dr

2 bd · 1.5 ba · 984 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$86,505Oct 2015 $3,7962025 Amount on Record Aug 2015 2 Names on Record Assessor + 1 DocumentUpdated May 2026

4844 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$53,600Apr 1998 $9292025 1 Name on Record Owner Occupied AssessorUpdated May 2026

4847 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$370,000Oct 2024 $4,3322025 Amount on Record Jul 2017 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

4854 Headlee Dr

3 bd · 1.5 ba · 984 sqft · 0.167 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$70,000Apr 2023 $3,3062025 Amount on Record Mar 2011 1 Name on Record AssessorUpdated Aug 2026

4855 Headlee Dr

3 bd · 1.5 ba · 1,000 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$70,900Apr 2013 $3,2502025 Amount on Record Dec 2001 1 Name on Record Owner Occupied AssessorUpdated May 2026

4862 Headlee Dr

3 bd · 1.5 ba · 1,938 sqft · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,000Nov 2005 $4,5662025 Amount on Record Mar 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

4863 Headlee Dr

3 bd · 1.5 ba · 984 sqft · 0.178 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$44,000Dec 2010 $9592025 —Nov 2010 1 Name on Record Owner Occupied AssessorUpdated May 2026

4871 Headlee Dr

3 bd · 1.5 ba · 1,385 sqft · 0.286 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Nov 2018 $2,5372025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

4879 Headlee Dr

4 bd · 1.5 ba · 1,124 sqft · 0.207 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,8612025 2 Names on Record Owner Occupied AssessorUpdated May 2026

4887 Headlee Dr

3 bd · 1.5 ba · 1,387 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$136,000Apr 2005 $9052025 Amount on Record Jun 2003 2 Names on Record Owner Occupied AssessorUpdated May 2026

4895 Headlee Dr

3 bd · 2 ba · 984 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,2742025 2 Names on Record AssessorUpdated May 2026

4901 Headlee Dr

3 bd · 1.5 ba · 1,274 sqft · 0.207 acres

Last Sale Tax Bill Prior Sale Owner Records
$104,400Dec 2008 $9252025 —Apr 2008 1 Name on Record Owner Occupied AssessorUpdated May 2026

4904 Headlee Dr

4 bd · 2.5 ba · 1,360 sqft · 0.286 acres

Last Sale Tax Bill Prior Sale Owner Records
$8692025 1 Name on Record Owner Occupied AssessorUpdated May 2026

4909 Headlee Dr

4 bd · 1.5 ba · 1,516 sqft · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$86,000Mar 2001 $9712025 Amount on Record Apr 1999 1 Name on Record Owner Occupied AssessorUpdated May 2026

4910 Headlee Dr

3 bd · 1.5 ba · 1,392 sqft · 0.178 acres

Last Sale Tax Bill Prior Sale Owner Records
$59,000Dec 1994 $9992025 2 Names on Record Owner Occupied AssessorUpdated May 2026

4916 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$9502025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

4921 Headlee Dr

3 bd · 1.5 ba · 1,432 sqft · 0.167 acres

Last Sale Tax Bill Prior Sale Owner Records
$27,000Feb 1996 $9612025 Amount on Record Oct 1995 1 Name on Record Owner Occupied AssessorUpdated May 2026

4922 Headlee Dr

3 bd · 1.5 ba · 1,213 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000Aug 2021 $5,3622025 Amount on Record Feb 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

4929 Headlee Dr

3 bd · 1.5 ba · 1,221 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$192,000Mar 2019 $2,6382025 Amount on Record Jul 2016 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5000 Headlee Dr

3 bd · 1.5 ba · 984 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$350,000Nov 2025 $4,1212025 Amount on Record Jan 2016 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5001 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$205,000May 2007 $9822025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5005 Headlee Dr

4 bd · 2.5 ba · 1,419 sqft · 0.167 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$60,000May 2014 $4,2932025 Amount on Record Nov 1994 1 Name on Record AssessorUpdated May 2026

5006 Headlee Dr

3 bd · 1.5 ba · 1,015 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$235,000Mar 2022 $4,0172025 Amount on Record May 2003 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

5017 Headlee Dr

3 bd · 1.5 ba · 1,728 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,2492025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5018 Headlee Dr

3 bd · 1.5 ba · 1,401 sqft · 0.179 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000May 2016 $4,2092025 Amount on Record Jan 2015 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5025 Headlee Dr

3 bd · 1.5 ba · 1,211 sqft · Garage

Last Sale Tax Bill Prior Sale Owner Records
$190,000Dec 2017 $2,4502025 Amount on Record Jun 2009 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5101 Headlee Dr

2 bd · 1.5 ba · 1,219 sqft · 0.167 acres

Last Sale Tax Bill Prior Sale Owner Records
$27,500Oct 2001 $9422025 Amount on Record Sep 1993 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5107 Headlee Dr

4 bd · 2 ba · 1,399 sqft · 0.179 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$63,000Feb 2011 $3,8432025 —Sep 2010 1 Name on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Headlee Dr

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

Wildfire RiskLow
this street's cells rank at the 3rd percentile of exposed land nationally · 3rd in Florida
Wildfire LikelihoodLow — about 1 in 9,677 per year
ExposureDirect
1 of 3 cells directly exposed · 2 adjoin burnable vegetation

Property Records in Nearby Streets