Windward Dr, Chesapeake, VA Property Records

Chesapeake City property records for 47 addresses on Windward Dr, Chesapeake, VA · Last verified July 2026

Windward Dr Highlights

Properties 47
Median Sale Price $405,000
Deeds and Mortgages on File 92
Median Price per Sqft $192
Owner Occupied 89%
Median Annual Tax Bill $4,158
Median Year Built 1996
Median Ownership Tenure 12 years

Properties on Windward Dr

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

500 Windward Dr

3 bd · 2 ba · 1,332 sqft · 0.151 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$199,500Dec 2004 $3,5092025 Amount on Record Nov 2001 2 Names on Record Assessor + 2 DocumentsUpdated Jun 2026

501 Windward Dr

4 bd · 2.5 ba · 2,152 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$300,000Apr 2020 $4,4062025 Amount on Record Feb 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

502 Windward Dr

4 bd · 2.5 ba · 1,978 sqft · 0.123 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$299,000Dec 2006 $4,0632025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

504 Windward Dr

4 bd · 3 ba · 2,054 sqft · 0.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$312,000Aug 2019 $4,1892025 Amount on Record Mar 2007 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

505 Windward Dr

4 bd · 2.5 ba · 2,630 sqft · 0.128 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Oct 2018 $4,4932025 Amount on Record May 2007 2 Names on Record Assessor + 6 DocumentsUpdated Jun 2026

508 Windward Dr

4 bd · 2.5 ba · 2,087 sqft · 0.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$360,000May 2021 $4,3362025 Amount on Record Dec 2004 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

509 Windward Dr

3 bd · 2.5 ba · 2,416 sqft · 0.155 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,400Jun 1996 $4,3212025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

510 Windward Dr

3 bd · 2 ba · 1,499 sqft · 0.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$390,000Apr 2022 $2,6522019 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

512 Windward Dr

4 bd · 2.5 ba · 2,229 sqft · 0.128 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$435,000Sep 2024 $4,3072025 Amount on Record Sep 2023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

513 Windward Dr

3 bd · 2.5 ba · 1,629 sqft · 0.132 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$461,400Jan 2025 $4,0342025 Amount on Record May 2023 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

514 Windward Dr

4 bd · 2.5 ba · 2,165 sqft · 0.116 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jan 1997 $4,3012025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

516 Windward Dr

3 bd · 2.5 ba · 2,255 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$305,900Aug 2017 $4,3252025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

517 Windward Dr

4 bd · 2.5 ba · 2,143 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$132,200Jan 1997 $4,2262025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

518 Windward Dr

4 bd · 2.5 ba · 2,091 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jan 2025 $4,4162025 Amount on Record Aug 2004 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Jun 2026

519 Windward Dr

4 bd · 2.5 ba · 2,600 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$425,000Jun 2026 $4,6352025 Amount on Record Mar 2011 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

520 Windward Dr

3 bd · 2 ba · 1,665 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$405,000May 2026 $9382025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

521 Windward Dr

3 bd · 2.5 ba · 2,308 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$300,000Mar 2016 $4,3522025 Amount on Record Jun 2011 1 Name on Record Assessor + 2 DocumentsUpdated Jun 2026

522 Windward Dr

4 bd · 2.5 ba · 2,498 sqft · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Jul 2023 $4,1152023 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

523 Windward Dr

3 bd · 2.5 ba · 1,986 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$279,000Jul 2013 $4,0632025 Amount on Record Nov 2012 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

524 Windward Dr

3 bd · 2 ba · 1,588 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$279,900Mar 2007 $3,8062025 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated Jun 2026

525 Windward Dr

4 bd · 3 ba · 2,215 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000May 2012 $3,0942019 Amount on Record Nov 2003 1 Name on Record Owner Occupied AssessorUpdated Sep 2023

526 Windward Dr

3 bd · 2.5 ba · 1,471 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$119,900Dec 1996 $3,6212025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

527 Windward Dr

4 bd · 2.5 ba · 2,099 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$399,900Oct 2022 $4,2512025 Amount on Record Oct 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

528 Windward Dr

3 bd · 2 ba · 1,506 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jun 2017 $3,7302025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

529 Windward Dr

4 bd · 2.5 ba · 2,091 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2001 $4,1852025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

530 Windward Dr

4 bd · 3 ba · 2,141 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$290,000Nov 2009 $2,9872019 Amount on Record Dec 2002 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

532 Windward Dr

4 bd · 2.5 ba · 1,901 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$148,000Apr 2001 $4,0512025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

534 Windward Dr

4 bd · 2.5 ba · 2,020 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$298,000Nov 2020 $4,1142025 Amount on Record Apr 2006 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

600 Windward Dr

4 bd · 2.5 ba · 2,166 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$209,000Sep 2010 $4,2342025 Amount on Record Mar 2010 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

602 Windward Dr

4 bd · 2.5 ba · 2,099 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$395,000Dec 2021 $4,2202025 Amount on Record Jul 2006 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

604 Windward Dr

4 bd · 2.5 ba · 2,099 sqft · 0.114 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$282,000Apr 2012 $4,4442025 Amount on Record Oct 2007 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

606 Windward Dr

4 bd · 3 ba · 2,091 sqft · 0.114 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$315,000Aug 2006 $3,0832019 1 Name on Record Owner Occupied Assessor + 6 DocumentsUpdated Sep 2023

608 Windward Dr

4 bd · 2.5 ba · 2,074 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$415,000Jun 2023 $4,3472025 Amount on Record Apr 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

610 Windward Dr

4 bd · 2.5 ba · 1,897 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$264,900Aug 2014 $4,0202025 Amount on Record Feb 2011 2 Names on Record AssessorUpdated Jun 2026

612 Windward Dr

4 bd · 3 ba · 2,129 sqft · 0.114 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$435,000Jul 2023 $3,0072019 Amount on Record Dec 2019 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

614 Windward Dr

4 bd · 2.5 ba · 1,985 sqft · 0.119 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$122,000Dec 1995 $4,0612025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

616 Windward Dr

3 bd · 2 ba · 1,569 sqft · 0.157 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$250,600Sep 2006 $3,7822025 Amount on Record Apr 2001 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

617 Windward Dr

4 bd · 2.5 ba · 2,223 sqft · 0.167 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$246,500Jul 2004 $4,3012025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

618 Windward Dr

4 bd · 2.5 ba · 2,021 sqft · 0.201 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$126,600Jan 1996 $4,1582025 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

620 Windward Dr

3 bd · 2.5 ba · 2,391 sqft · 0.187 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$145,000Sep 1999 $4,4422025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

621 Windward Dr

3 bd · 2.5 ba · 1,954 sqft · 0.148 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$370,000Aug 2021 $4,0302025 Amount on Record Dec 2015 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

622 Windward Dr

4 bd · 3 ba · 2,108 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$270,000Jul 2015 $2,9692019 Amount on Record Sep 2012 1 Name on Record Owner Occupied Assessor + 6 DocumentsUpdated Sep 2023

623 Windward Dr

4 bd · 2.5 ba · 2,164 sqft · 0.176 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$150,000Jun 2000 $4,2242025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

624 Windward Dr

3 bd · 2.5 ba · 1,986 sqft · 0.194 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—May 2005 $4,0632025 1 Name on Record Owner Occupied AssessorUpdated Jun 2026

625 Windward Dr

3 bd · 2.5 ba · 1,957 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$376,000Nov 2021 $4,1872025 Amount on Record Jun 2018 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jun 2026

626 Windward Dr

3 bd · 2.5 ba · 1,793 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$265,000Aug 2015 $3,9012025 Amount on Record Oct 2008 2 Names on Record Owner Occupied AssessorUpdated Jun 2026

627 Windward Dr

4 bd · 2.5 ba · 2,164 sqft · 0.192 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$275,000Apr 2005 $4,2612025 Amount on Record Dec 2000 1 Name on Record Assessor + 1 DocumentUpdated Jun 2026

Property Records in Nearby Streets