Oak Bay Dr, Osprey, FL Property Records

Sarasota County property records for 52 addresses on Oak Bay Dr, Osprey, FL · Last verified August 2026

Oak Bay Dr Highlights

Properties 52
Median Sale Price $540,000
Deeds and Mortgages on File 81
Median Price per Sqft $259
Owner Occupied 90%
Median Annual Tax Bill $3,795
Median Year Built 1997
Median Ownership Tenure 9 years

Properties on Oak Bay Dr

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

500 Oak Bay Dr

3 bd · 3 ba · 2,459 sqft · built 1996 · 0.355 acres

Last Sale Tax Bill Prior Sale Owner Records
$700,000Jan 2022 $6,3672025 —Oct 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

502 Oak Bay Dr

3 bd · 2 ba · 2,116 sqft · built 1995 · 0.272 acres

Last Sale Tax Bill Prior Sale Owner Records
$495,000Dec 2024 $4,7672025 Amount on Record Jul 2000 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

503 Oak Bay Dr

3 bd · 2 ba · 2,049 sqft · built 2004 · 0.299 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,000Oct 2013 $1,0242025 Amount on Record Apr 2004 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

506 Oak Bay Dr

3 bd · 3 ba · 1,944 sqft · built 1995 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$655,000Oct 2023 $5,0172025 —Oct 2023 1 Name on Record Assessor + 3 DocumentsUpdated Jan 2026

507 Oak Bay Dr

3 bd · 3 ba · 1,982 sqft · built 1994 · 0.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3232025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

510 Oak Bay Dr

3 bd · 3 ba · 2,417 sqft · built 1997 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$224,500Dec 2002 $2,8072025 Amount on Record Mar 1997 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

511 Oak Bay Dr

4 bd · 3 ba · 2,097 sqft · built 1996 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$180,000Dec 1999 $2,8562025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

514 Oak Bay Dr

3 bd · 2 ba · 1,846 sqft · built 1999 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$672,000Nov 2022 $4,9582025 Amount on Record Jun 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

515 Oak Bay Dr

3 bd · 2 ba · 1,977 sqft · built 1995 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$512,500Sep 2024 $4,5522025 Amount on Record Apr 2005 2 Names on Record AssessorUpdated Jan 2026

518 Oak Bay Dr

4 bd · 3 ba · 2,162 sqft · built 1998 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$365,000Aug 2016 $3,5702025 Amount on Record Dec 2011 2 Names on Record Owner Occupied AssessorUpdated Jan 2026

519 Oak Bay Dr

3 bd · 2 ba · 2,305 sqft · built 1997 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$229,900Jan 2012 $4,7582025 Amount on Record Feb 2001 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

520 Oak Bay Dr

3 bd · 2 ba · 1,958 sqft · built 1998 · 0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$565,000Nov 2021 $5,4982025 Amount on Record Feb 2021 2 Names on Record Assessor + 3 DocumentsUpdated Jan 2026

522 Oak Bay Dr

3 bd · 3 ba · 2,299 sqft · built 1998 · 0.423 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Apr 2015 $3,6042025 Amount on Record Mar 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

523 Oak Bay Dr

3 bd · 2 ba · 2,399 sqft · built 1998 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$540,000Aug 2026 $3,4482025 Amount on Record Sep 1997 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

524 Oak Bay Dr

4 bd · 3 ba · 2,768 sqft · built 1998 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Apr 2006 $4,9062025 —Dec 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

526 Oak Bay Dr

3 bd · 2 ba · 1,917 sqft · built 1998 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$265,000May 2015 $2,7202025 Amount on Record Nov 1998 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

530 Oak Bay Dr

4 bd · 3 ba · 2,369 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$371,100Apr 2020 $3,9802025 —Jan 2011 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

534 Oak Bay Dr

4 bd · 3 ba · 2,077 sqft · built 1996 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000May 2011 $5,8012025 Amount on Record Sep 2003 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

538 Oak Bay Dr

4 bd · 3 ba · 2,200 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Jul 2016 $3,3082025 —May 2010 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

542 Oak Bay Dr

3 bd · 2 ba · 2,046 sqft · built 1996 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Dec 2020 $4,8282025 —Jun 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

543 Oak Bay Dr

3 bd · 3 ba · 2,575 sqft · built 1999 · 0.253 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Apr 2011 $2,7722025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

546 Oak Bay Dr

4 bd · 3 ba · 2,504 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Sep 2004 $3,7892025 Amount on Record Apr 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

547 Oak Bay Dr

3 bd · 2 ba · 1,855 sqft · built 1998 · 0.252 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Sep 2002 $2,4712025 Amount on Record Oct 1998 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

550 Oak Bay Dr

3 bd · 2 ba · 2,374 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$289,900Apr 2003 $2,6542025 Amount on Record Dec 1999 2 Names on Record Owner Occupied AssessorUpdated Jan 2026

551 Oak Bay Dr

0.014 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record Owner Occupied AssessorUpdated Jan 2026

554 Oak Bay Dr

4 bd · 2 ba · 1,749 sqft · built 1999 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Jul 2022 $4,0372025 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jan 2026

558 Oak Bay Dr

3 bd · 2 ba · 2,548 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$324,750Aug 2014 $4,3192025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

562 Oak Bay Dr

3 bd · 2.5 ba · 2,414 sqft · built 1995 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$511,500Jun 2026 $3,5232025 Amount on Record Sep 1995 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

566 Oak Bay Dr

3 bd · 2 ba · 2,559 sqft · built 1997 · 0.244 acres

Last Sale Tax Bill Prior Sale Owner Records
$520,000Feb 2026 $6,5172025 Amount on Record Nov 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

570 Oak Bay Dr

3 bd · 2.5 ba · 1,816 sqft · built 1999 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$287,000Feb 2015 $4,0312025 Amount on Record Nov 2011 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

574 Oak Bay Dr

3 bd · 3 ba · 2,325 sqft · built 1999 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$625,000Jul 2023 $2,1482025 3 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

578 Oak Bay Dr

3 bd · 2 ba · 2,404 sqft · built 1998 · 0.238 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Nov 2006 $2,8892025 —May 2021 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

579 Oak Bay Dr

4 bd · 3 ba · 2,721 sqft · built 1995 · 0.268 acres

Last Sale Tax Bill Prior Sale Owner Records
$830,000Aug 2022 $8,4092024 Amount on Record May 2020 1 Name on Record Assessor + 3 DocumentsUpdated Apr 2026

582 Oak Bay Dr

3 bd · 2 ba · 2,275 sqft · built 1998 · 0.248 acres

Last Sale Tax Bill Prior Sale Owner Records
$211,000Oct 1998 $2,7902025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

583 Oak Bay Dr

4 bd · 3 ba · 2,489 sqft · built 1999 · 0.268 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Sep 2015 $3,9122025 Amount on Record Dec 2009 2 Names on Record Owner Occupied AssessorUpdated Jan 2026

586 Oak Bay Dr

3 bd · 2 ba · 2,084 sqft · built 2003 · 0.248 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Sep 2013 $3,9842025 Amount on Record Jan 2002 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

587 Oak Bay Dr

3 bd · 2.5 ba · 2,059 sqft · built 1995 · 0.288 acres

Last Sale Tax Bill Prior Sale Owner Records
$349,500Nov 2017 $4,1942025 Amount on Record Mar 2013 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

590 Oak Bay Dr

3 bd · 2 ba · 1,892 sqft · built 1999 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$609,000Oct 2023 $4,3102025 Amount on Record Feb 2017 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

591 Oak Bay Dr

3 bd · 2 ba · 2,416 sqft · built 1998 · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$232,900Apr 2009 $6,2742024 —Dec 2008 1 Name on Record Assessor + 3 DocumentsUpdated Apr 2026

594 Oak Bay Dr

3 bd · 2 ba · 1,844 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$166,800Apr 1998 $2,2452025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

595 Oak Bay Dr

4 bd · 3 ba · 2,241 sqft · built 1996 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Apr 2021 $4,7812025 Amount on Record Dec 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

598 Oak Bay Dr

3 bd · 2 ba · 2,319 sqft · built 1997 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$61,000Jul 1997 $2,5972025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

599 Oak Bay Dr

3 bd · 2 ba · 2,037 sqft · built 2002 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$595,000Jan 2023 $4,8822025 Amount on Record Feb 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

602 Oak Bay Dr

2 bd · 2 ba · 1,832 sqft · built 2002 · 0.261 acres

Last Sale Tax Bill Prior Sale Owner Records
$27,000Oct 2001 $2,0212025 1 Name on Record Owner Occupied AssessorUpdated Jan 2026

603 Oak Bay Dr

4 bd · 2 ba · 2,312 sqft · built 1997 · 0.261 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Aug 2024 $4,7122025 —Jun 2020 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

608 Oak Bay Dr

3 bd · 2 ba · 2,058 sqft · built 1998 · 0.258 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Jun 2020 $3,7192024 Amount on Record Jul 2010 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

612 Oak Bay Dr

3 bd · 2 ba · 1,915 sqft · built 2002 · 0.267 acres

Last Sale Tax Bill Prior Sale Owner Records
$363,000Oct 2017 $3,4042025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jan 2026

616 Oak Bay Dr

3 bd · 3 ba · 2,333 sqft · built 1997 · 0.236 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Nov 2019 $3,7422025 Amount on Record Nov 2009 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

620 Oak Bay Dr

3 bd · 2 ba · 2,267 sqft · built 1995 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Nov 2019 $3,6012025 —Aug 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

624 Oak Bay Dr

3 bd · 2 ba · 1,929 sqft · built 1997 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$224,000Jul 2009 $2,4802025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

628 Oak Bay Dr

4 bd · 3 ba · 2,596 sqft · built 1997 · 0.268 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000May 2018 $3,7952025 Amount on Record Mar 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

629 Oak Bay Dr

4 bd · 2 ba · 1,867 sqft · built 1996 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2025 $4,2372025 Amount on Record Apr 2023 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

Wildfire Risk on Oak Bay Dr

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

Wildfire RiskModerate
this street's cells rank above 46% of the US · above 19% of Florida
Wildfire LikelihoodAbout 1 in 1,072 per year
ExposureDirect
1 of 4 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets