Hillside Dr, Orlando, FL Property Records

Orange County property records for 27 addresses on Hillside Dr, Orlando, FL · Last verified August 2026

Hillside Dr Highlights

Properties 27
Median Sale Price $299,000
Deeds and Mortgages on File 44
Median Price per Sqft $176
Owner Occupied 74%
Median Annual Tax Bill $3,939
Median Year Built 1976
Median Ownership Tenure 11 years

Properties on Hillside Dr

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

5301 Hillside Dr

3 bd · 2 ba · 1,480 sqft · 0.227 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5972025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5305 Hillside Dr

4 bd · 2 ba · 1,846 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jun 2019 $3,7302025 Amount on Record Feb 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5306 Hillside Dr

4 bd · 3 ba · 2,117 sqft · 0.237 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$299,000Jun 2019 $4,2062025 Amount on Record Sep 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5309 Hillside Dr

3 bd · 2 ba · 1,666 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$119,000Dec 2002 $5,6252025 2 Names on Record AssessorUpdated May 2026

5312 Hillside Dr

4 bd · 2 ba · 1,674 sqft · 0.225 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$187,500Aug 2016 $5,2762025 Amount on Record Aug 2003 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

5315 Hillside Dr

3 bd · 2 ba · 1,358 sqft · 0.202 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$119,000Aug 2015 $2,0592025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5318 Hillside Dr

4 bd · 2 ba · 1,846 sqft · 0.23 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$214,147Apr 2020 $6,1752025 Amount on Record Sep 2019 1 Name on Record Assessor + 2 DocumentsUpdated May 2026

5321 Hillside Dr

4 bd · 2 ba · 1,858 sqft · 0.22 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$271,000Mar 2021 $5,8002025 Amount on Record May 2017 2 Names on Record Assessor + 5 DocumentsUpdated May 2026

5324 Hillside Dr

3 bd · 2 ba · 1,480 sqft · 0.231 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$382,200Jul 2022 $6,4322025 Amount on Record Jun 2021 2 Names on Record Assessor + 2 DocumentsUpdated May 2026

5330 Hillside Dr

3 bd · 2 ba · 1,663 sqft · 0.231 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$118,500Aug 2001 $1,6622025 Amount on Record Jun 1995 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5333 Hillside Dr

5 bd · 2.5 ba · 2,076 sqft · 0.233 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Aug 2018 $4782025 Amount on Record Dec 2015 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

5336 Hillside Dr

4 bd · 2 ba · 1,666 sqft · 0.252 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,6872025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5342 Hillside Dr

3 bd · 2 ba · 1,358 sqft · 0.234 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$155,000Apr 2014 $3,9392025 2 Names on Record Owner Occupied AssessorUpdated May 2026

8665 Hillside Dr

3 bd · 2 ba · 1,666 sqft · 0.211 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$5,6342025 2 Names on Record AssessorUpdated May 2026

8670 Hillside Dr

3 bd · 2 ba · 1,703 sqft · 0.224 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$185,000Oct 2015 $2,7642025 Amount on Record Jun 2015 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

8671 Hillside Dr

4 bd · 2 ba · 1,672 sqft · 0.211 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4782025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

8676 Hillside Dr

3 bd · 2 ba · 1,694 sqft · 0.206 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$299,000Apr 2025 $6,1942025 2 Names on Record AssessorUpdated Jul 2026

8677 Hillside Dr

5 bd · 2 ba · 1,805 sqft · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$278,500Aug 2020 $4,8702025 Amount on Record Dec 2019 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

8682 Hillside Dr

3 bd · 2 ba · 1,358 sqft · 0.223 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$87,700Nov 1997 $1,6532025 2 Names on Record Owner Occupied AssessorUpdated May 2026

8683 Hillside Dr

4 bd · 2 ba · 1,456 sqft · 0.197 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$379,000Dec 2024 $4,8302025 Amount on Record Jul 2001 2 Names on Record Owner Occupied AssessorUpdated May 2026

8687 Hillside Dr

4 bd · 2 ba · 1,846 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$250,000Sep 2007 $5,6102025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

8690 Hillside Dr

3 bd · 2 ba · 1,894 sqft · 0.224 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$143,000Jun 2003 $1,9422025 Amount on Record May 2002 2 Names on Record Owner Occupied AssessorUpdated May 2026

8691 Hillside Dr

3 bd · 2 ba · 1,982 sqft · 0.198 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$240,000Jul 2005 $2,3072025 Amount on Record May 2005 2 Names on Record Owner Occupied AssessorUpdated May 2026

8695 Hillside Dr

3 bd · 2 ba · 1,502 sqft · 0.198 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$204,900Mar 2006 $5,6242025 Amount on Record Sep 2005 1 Name on Record Assessor + 1 DocumentUpdated May 2026

8696 Hillside Dr

3 bd · 2 ba · 1,480 sqft · 0.206 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$76,500Sep 1995 $1,5232025 1 Name on Record Owner Occupied AssessorUpdated May 2026

8698 Hillside Dr

4 bd · 2.5 ba · 2,512 sqft · 0.224 acres

Last Sale Tax Bill Prior Sale Owner Records
$112,500Aug 2000 $2,0692025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

8699 Hillside Dr

4 bd · 2.5 ba · 2,083 sqft · 0.221 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$375,000Dec 2022 $4,3232025 Amount on Record Oct 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

Wildfire Risk on Hillside Dr

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach of burnable land

Property Records in Nearby Streets