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Oak Hill Dr, Winter Park, FL Property Records

Seminole County property records for 30 addresses on Oak Hill Dr, Winter Park, FL · Last verified October 2026

Oak Hill Dr Highlights

Properties 30
Median Sale Price $280,000
Deeds and Mortgages on File 39
Median Price per Sqft $199
Owner Occupied 67%
Median Annual Tax Bill $2,021
Median Year Built 1972
Median Ownership Tenure 13 years

Properties on Oak Hill Dr

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

5017 Oak Hill Dr

3 bd · 2 ba · 1,640 sqft · built 1973 · 0.216 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,900Jan 2019 $4,8712025 Amount on Record Nov 2018 Owner on Record Assessor + 5 DocumentsUpdated Aug 2026

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5018 Oak Hill Dr

2 bd · 2 ba · 1,092 sqft · built 1972 · 0.214 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Apr 2005 $9692025 —Oct 1978 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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5023 Oak Hill Dr

3 bd · 2 ba · 1,324 sqft · built 1972 · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$83,000May 1998 $9822025 Amount on Record — Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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5024 Oak Hill Dr

2 bd · 2 ba · 1,070 sqft · built 1972 · 0.323 acres

Last Sale Tax Bill Prior Sale Owner Records
$84,000Jan 2003 $2,7652025 Amount on Record Nov 1998 2 Owners on Record AssessorUpdated Dec 2025

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5029 Oak Hill Dr

2 bd · 2 ba · 480 sqft · built 2020 · 0.256 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Apr 2017 $2,0212025 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Dec 2025

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5030 Oak Hill Dr

3 bd · 2 ba · 978 sqft · built 1972 · 0.226 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Jun 2022 $3,5032025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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5035 Oak Hill Dr

3 bd · 2 ba · 1,036 sqft · built 1972 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Dec 2019 $1,6842025 Amount on Record Dec 2010 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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5036 Oak Hill Dr

2 bd · 2 ba · 1,020 sqft · built 1972 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2005 $6432025 Amount on Record Jan 1972 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

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5041 Oak Hill Dr

2 bd · 2 ba · 964 sqft · built 1972 · 0.219 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,100May 2012 $3,0832025 Amount on Record May 2002 Owner on Record AssessorUpdated Oct 2026

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5042 Oak Hill Dr

3 bd · 2 ba · 1,486 sqft · built 1972 · 0.261 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 1998 $9762025 2 Owners on Record Owner Occupied AssessorUpdated Dec 2025

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5047 Oak Hill Dr

3 bd · 2 ba · 1,546 sqft · built 1972 · 0.273 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,2342025 4 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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5048 Oak Hill Dr

2 bd · 2 ba · 964 sqft · built 1972 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,500Mar 2013 $3,1022025 —Jun 2006 Owner on Record Assessor + 1 DocumentUpdated Apr 2026

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5102 Oak Hill Dr

2 bd · 2 ba · 1,150 sqft · built 1972 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Sep 2014 $1,1042025 —Feb 2001 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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5103 Oak Hill Dr

3 bd · 2 ba · 2,028 sqft · built 1972 · 0.22 acres

Last Sale Tax Bill Prior Sale Owner Records
$82,000May 2001 $3,5292025 —Apr 2001 Owner on Record AssessorUpdated Oct 2026

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5108 Oak Hill Dr

3 bd · 2 ba · 1,020 sqft · built 1972 · 0.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000May 2019 $2,8502025 —Sep 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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5109 Oak Hill Dr

3 bd · 2 ba · 1,682 sqft · built 1972 · 0.216 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Jun 2016 $1,2762025 Amount on Record Feb 1994 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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5114 Oak Hill Dr

3 bd · 2 ba · 1,447 sqft · built 1972 · 0.227 acres

Last Sale Tax Bill Prior Sale Owner Records
$65,500Dec 1986 $1,0662025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

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5115 Oak Hill Dr

3 bd · 2 ba · 1,524 sqft · built 1972 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Aug 1998 $1,0882025 Amount on Record Feb 1998 Owner on Record Owner Occupied AssessorUpdated Apr 2026

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5120 Oak Hill Dr

3 bd · 2 ba · 1,338 sqft · built 1972 · 0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$183,000Jun 2017 $2,1132025 Amount on Record Feb 2013 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

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5121 Oak Hill Dr

3 bd · 2 ba · 1,652 sqft · built 1972 · 0.262 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,700Mar 2001 $1,1402025 Amount on Record Jul 1995 Owner on Record Owner Occupied AssessorUpdated Dec 2025

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5126 Oak Hill Dr

3 bd · 2 ba · 1,760 sqft · built 1972 · 0.252 acres

Last Sale Tax Bill Prior Sale Owner Records
$69,500Dec 1995 $5532025 2 Owners on Record Owner Occupied AssessorUpdated Dec 2025

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5127 Oak Hill Dr

3 bd · 2.5 ba · 1,772 sqft · built 1972 · 0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$353,000Mar 2022 $5,2292025 Amount on Record May 2016 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

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5132 Oak Hill Dr

2 bd · 1 ba · 1,020 sqft · built 1972 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Jun 1996 $3,0022025 Amount on Record May 1980 Owner on Record AssessorUpdated Oct 2026

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5133 Oak Hill Dr

3 bd · 2 ba · 1,896 sqft · built 1972 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Dec 2019 $4,2992025 Amount on Record Nov 2015 Owner on Record Assessor + 3 DocumentsUpdated Apr 2026

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5138 Oak Hill Dr

2 bd · 2 ba · 981 sqft · built 1972 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
$280,000Jul 2026 $2,9992025 Amount on Record Nov 1979 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

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5139 Oak Hill Dr

2 bd · 2 ba · 1,104 sqft · built 1972 · 0.22 acres

Last Sale Tax Bill Prior Sale Owner Records
$77,100Apr 2017 $3,0942025 Amount on Record Jan 1977 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

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5144 Oak Hill Dr

3 bd · 2 ba · 1,372 sqft · built 1972 · 0.242 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2016 $1,8052025 Owner on Record Owner Occupied AssessorUpdated Jan 2026

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5145 Oak Hill Dr

3 bd · 2 ba · 1,378 sqft · built 1972 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Mar 2022 $3,9412025 Amount on Record Dec 1995 2 Owners on Record Assessor + 2 DocumentsUpdated Dec 2025

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5150 Oak Hill Dr

3 bd · 2 ba · 1,650 sqft · built 1972 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jul 2004 $1,1432025 Amount on Record Jun 2004 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

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5151 Oak Hill Dr

4 bd · 2 ba · 2,434 sqft · built 1972 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$53,500May 2010 $1,5472025 Amount on Record Jan 2004 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

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Property Records in Nearby Streets