Winter Run Dr, Orlando, FL Property Records

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

Winter Run Dr Highlights

Properties 27
Median Sale Price $257,000
Deeds and Mortgages on File 18
Median Price per Sqft $227
Owner Occupied 63%
Median Annual Tax Bill $1,875
Median Year Built 1980
Median Ownership Tenure 14 years

Properties on Winter Run Dr

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

5303 Winter Run Dr

4 bd · 1.5 ba · 1,132 sqft · built 1980 · 0.291 acres

Last Sale Tax Bill Prior Sale Owner Records
$257,000Jul 2021 $3,7472025 —Jan 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5309 Winter Run Dr

4 bd · 1.5 ba · 1,132 sqft · built 1980 · 0.174 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Aug 2005 $3,5312025 2 Names on Record AssessorUpdated May 2026

5315 Winter Run Dr

2 bd · 1.5 ba · 1,381 sqft · built 1980 · 0.174 acres

Last Sale Tax Bill Prior Sale Owner Records
$59,000Aug 1995 $1,1942025 2 Names on Record Owner Occupied AssessorUpdated May 2026

5321 Winter Run Dr

3 bd · 1.5 ba · 1,037 sqft · built 1980 · 0.174 acres

Last Sale Tax Bill Prior Sale Owner Records
$64,000Mar 2010 $3,6102025 —May 2009 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

5322 Winter Run Dr

3 bd · 1.5 ba · 1,050 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jun 2025 $3,4352025 Amount on Record Apr 2023 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5327 Winter Run Dr

4 bd · 1.5 ba · 1,132 sqft · built 1980 · 0.174 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,4672025 2 Names on Record AssessorUpdated May 2026

5328 Winter Run Dr

3 bd · 2 ba · 1,675 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,0902025 2 Names on Record AssessorUpdated May 2026

5333 Winter Run Dr

2 bd · 1.5 ba · 976 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000May 2021 $3,9202025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5334 Winter Run Dr

3 bd · 1.5 ba · 934 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Feb 2026 $3,6002025 Amount on Record Nov 1997 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

5401 Winter Run Dr

2 bd · 1.5 ba · 1,260 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jul 2021 $3,2692025 Amount on Record Jul 2017 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

5404 Winter Run Dr

3 bd · 1.5 ba · 1,326 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$125,500Oct 2015 $1,7762025 —Sep 2015 1 Name on Record Owner Occupied AssessorUpdated May 2026

5407 Winter Run Dr

3 bd · 1.5 ba · 942 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$119,000May 2005 $3,2702025 Amount on Record Jun 2003 2 Names on Record AssessorUpdated May 2026

5410 Winter Run Dr

4 bd · 1.5 ba · 1,230 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$32,500Nov 2003 $1,0912025 1 Name on Record Owner Occupied AssessorUpdated May 2026

5413 Winter Run Dr

3 bd · 1.5 ba · 1,035 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jun 2023 $3,3322025 Amount on Record Apr 2005 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

5416 Winter Run Dr

3 bd · 2 ba · 1,080 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,4362025 2 Names on Record AssessorUpdated May 2026

5419 Winter Run Dr

3 bd · 1.5 ba · 1,116 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$61,000Nov 1998 $3,3422025 Amount on Record Apr 1998 2 Names on Record AssessorUpdated May 2026

5422 Winter Run Dr

3 bd · 1.5 ba · 1,035 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$52,000Jul 2012 $9252025 Amount on Record Dec 2005 1 Name on Record Owner Occupied AssessorUpdated May 2026

5425 Winter Run Dr

4 bd · 1.5 ba · 1,169 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$178,000Jun 2019 $4,1522025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

5428 Winter Run Dr

4 bd · 1.5 ba · 1,510 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$79,900Aug 2012 $1,2272025 Amount on Record Jan 2006 1 Name on Record Owner Occupied AssessorUpdated May 2026

5431 Winter Run Dr

2 bd · 1.5 ba · 976 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$94,000Jul 2014 $1,4002025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

5434 Winter Run Dr

3 bd · 1.5 ba · 1,169 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,0042025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

5437 Winter Run Dr

3 bd · 1.5 ba · 1,015 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$9032025 1 Name on Record Owner Occupied AssessorUpdated May 2026

5440 Winter Run Dr

3 bd · 2.5 ba · 1,400 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$128,000Nov 2004 $1,1252025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

5443 Winter Run Dr

3 bd · 2 ba · 1,880 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$59,400Dec 1994 $1,3172025 1 Name on Record Owner Occupied AssessorUpdated May 2026

5446 Winter Run Dr

3 bd · 2 ba · 1,080 sqft · built 1980 · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$49,500Aug 2016 $1,8752025 Amount on Record Jun 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

5447 Winter Run Dr

3 bd · 1.5 ba · 1,066 sqft · built 1980 · 0.157 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,000Dec 1997 $9772025 2 Names on Record Assessor + 1 DocumentUpdated May 2026

5452 Winter Run Dr

3 bd · 1.5 ba · 934 sqft · built 1980 · 0.193 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,000Mar 2005 $9782025 Amount on Record Jan 2001 2 Names on Record Owner Occupied AssessorUpdated May 2026

Wildfire Risk on Winter Run 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

Property Records in Nearby Streets