Winewood Dr, Sarasota, FL Property Records

Sarasota County property records for 27 addresses on Winewood Dr, Sarasota, FL · Last verified October 2026

Winewood Dr Highlights

Properties 27
Median Sale Price $278,000
Deeds and Mortgages on File 37
Median Price per Sqft $210
Owner Occupied 85%
Median Annual Tax Bill $1,919
Median Year Built 1978
Median Ownership Tenure 9 years

Properties on Winewood Dr

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

5308 Winewood Dr

3 bd · 2 ba · 1,076 sqft · built 1979 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Aug 2019 $1,6032025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5309 Winewood Dr

3 bd · 2 ba · 1,300 sqft · built 1979 · 0.232 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Sep 1987 $1,1432025 2 Owners on Record Owner Occupied AssessorUpdated Jan 2026

5322 Winewood Dr

4 bd · 2 ba · 1,492 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$9992025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5323 Winewood Dr

3 bd · 2 ba · 1,374 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2014 $3,1662025 Amount on Record Feb 2013 Owner on Record Assessor + 2 DocumentsUpdated Jan 2026

5336 Winewood Dr

2 bd · 2 ba · 1,272 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Nov 1999 $1,0712025 Owner on Record Owner Occupied AssessorUpdated Jan 2026

5337 Winewood Dr

3 bd · 2 ba · 1,212 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$169,900May 2017 $1,7092025 —Sep 2008 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

5351 Winewood Dr

3 bd · 3 ba · 1,430 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$226,000Jun 2019 $2,7092024 Amount on Record Dec 2016 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

5352 Winewood Dr

2 bd · 2 ba · 1,822 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Nov 1978 $1,5342025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

5364 Winewood Dr

3 bd · 2 ba · 1,661 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$422,500Dec 2024 $3,7412025 Owner on Record Owner Occupied AssessorUpdated Jan 2026

5365 Winewood Dr

2 bd · 2 ba · 1,274 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Jun 2001 $3,5402025 Owner on Record AssessorUpdated Jun 2026

5378 Winewood Dr

3 bd · 2 ba · 1,275 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$229,000Apr 2019 $3,9592024 Amount on Record Apr 2015 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

5379 Winewood Dr

3 bd · 2 ba · 1,107 sqft · built 1979 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$207,000Jun 2018 $3,6392025 Amount on Record Jun 2015 2 Owners on Record Assessor + 1 DocumentUpdated Jan 2026

5392 Winewood Dr

3 bd · 2 ba · 1,399 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$97,500Mar 2001 $1,2882025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5393 Winewood Dr

2 bd · 2 ba · 1,188 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Nov 2019 $1,9822025 —Nov 2000 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5410 Winewood Dr

4 bd · 2 ba · 1,685 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,500Nov 2011 $1,4182025 Amount on Record Oct 2010 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5411 Winewood Dr

3 bd · 2 ba · 1,274 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,1752025 —Feb 1999 3 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

5424 Winewood Dr

3 bd · 2 ba · 1,148 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,000Jun 2011 $1,4222024 Amount on Record Apr 2011 Owner on Record Owner Occupied AssessorUpdated Jul 2026

5425 Winewood Dr

3 bd · 2 ba · 1,186 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2025 $2,7922025 —Sep 2004 3 Owners on Record AssessorUpdated Jan 2026

5438 Winewood Dr

3 bd · 2 ba · 1,621 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,900Jan 2009 $1,5982024 —Sep 2008 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

5439 Winewood Dr

3 bd · 2 ba · 1,398 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$278,000Oct 2020 $4,6362025 Amount on Record Nov 2019 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

5452 Winewood Dr

3 bd · 2 ba · 2,057 sqft · built 1978 · 0.237 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4492025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

5453 Winewood Dr

3 bd · 2 ba · 1,610 sqft · built 1978 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Sep 2022 $3,6502024 Amount on Record Aug 2018 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

5466 Winewood Dr

3 bd · 2 ba · 1,212 sqft · built 1978 · 0.241 acres

Last Sale Tax Bill Prior Sale Owner Records
$363,000Feb 2023 $2,3132025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

5467 Winewood Dr

3 bd · 2 ba · 1,186 sqft · built 1978 · 0.204 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,1802025 —Jun 2013 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jan 2026

5481 Winewood Dr

3 bd · 2 ba · 1,936 sqft · built 1978 · 0.218 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Jul 2015 $3,3002025 Amount on Record Mar 2000 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

5494 Winewood Dr

3 bd · 2 ba · 1,492 sqft · built 1978 · 0.304 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Feb 2015 $1,9192025 3 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Feb 2026

5495 Winewood Dr

3 bd · 2 ba · 1,274 sqft · built 1978 · 0.271 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4472025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

Property Records in Nearby Streets