Oakleigh Dr, Maitland, FL Property Records

Orange County property records for 14 addresses on Oakleigh Dr, Maitland, FL · Last verified September 2026

Oakleigh Dr Highlights

Properties 14
Median Sale Price $725,000
Deeds and Mortgages on File 16
Median Price per Sqft $242
Owner Occupied 86%
Median Annual Tax Bill $7,274
Median Year Built 1968
Median Ownership Tenure 10 years

Properties on Oakleigh Dr

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

39 Oakleigh Dr

3 bd · 2.5 ba · 2,330 sqft · built 1972 · 0.384 acres

Last Sale Tax Bill Prior Sale Owner Records
$396,000May 2004 $4,1232025 Amount on Record Aug 1999 2 Owners on Record Owner Occupied AssessorUpdated May 2026

40 Oakleigh Dr

4 bd · 2.5 ba · 2,904 sqft · built 1969 · 0.366 acres

Last Sale Tax Bill Prior Sale Owner Records
$825,000Feb 2024 $8,5822025 2 Owners on Record Assessor + 3 DocumentsUpdated Jul 2026

41 Oakleigh Dr

4 bd · 3 ba · 2,583 sqft · built 1970 · 0.404 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Dec 1999 $4,9792025 Amount on Record May 1994 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

50 Oakleigh Dr

3 bd · 2.5 ba · 2,606 sqft · built 1969 · 0.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$348,000Apr 2013 $8,5902025 —Aug 2008 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

60 Oakleigh Dr

3 bd · 2.5 ba · 2,478 sqft · built 1969 · 0.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Jun 2020 $4,4462025 —Dec 2001 Owner on Record Owner Occupied AssessorUpdated May 2026

61 Oakleigh Dr

4 bd · 2 ba · 2,515 sqft · built 1967 · 0.426 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000May 2001 $3,9472025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

70 Oakleigh Dr

4 bd · 2.5 ba · 2,543 sqft · built 1968 · 0.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$725,000Jul 2020 $10,8912025 Amount on Record Mar 2006 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

80 Oakleigh Dr

5 bd · 3 ba · 3,142 sqft · built 1968 · 0.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$940,000Apr 2022 $12,9522025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

81 Oakleigh Dr

5 bd · 4 ba · 5,301 sqft · built 1965 · 0.451 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2742025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

90 Oakleigh Dr

4 bd · 2.5 ba · 2,552 sqft · built 1963 · 0.357 acres

Last Sale Tax Bill Prior Sale Owner Records
$610,000Jun 2018 $12,7662025 Amount on Record Aug 2013 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

100 Oakleigh Dr

9 bd · 10.5 ba · 11,622 sqft · built 1901 · 1.71 acres

Last Sale Tax Bill Prior Sale Owner Records
$967,500Aug 2016 $22,9442025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

101 Oakleigh Dr

4 bd · 3.5 ba · 2,909 sqft · built 1966 · 0.442 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000Dec 1994 $5,4442025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

104 Oakleigh Dr

4 bd · 3 ba · 3,157 sqft · built 1999 · 0.364 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,0932025 2 Owners on Record AssessorUpdated May 2026

105 Oakleigh Dr

4 bd · 3.5 ba · 3,086 sqft · built 1963 · 0.444 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,6752025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

Property Records in Nearby Streets