Windward Key Dr, Chesapeake Beach, MD Property Records

Calvert County property records for 88 addresses on Windward Key Dr, Chesapeake Beach, MD · Last verified August 2026

Windward Key Dr Highlights

Properties 88
Median Sale Price $690,000
Deeds and Mortgages on File 92
Median Price per Sqft $313
Owner Occupied 56%
Median Annual Tax Bill $6,489
Median Year Built 1989
Median Ownership Tenure 12 years

Properties on Windward Key Dr

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

Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
—Jun 2001 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$16,750Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 Amount on Record May 2001 1 Name on Record Owner Occupied AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 Amount on Record Jun 2003 1 Name on Record AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 Amount on Record Aug 2004 1 Name on Record Owner Occupied AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
$16,000Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 Amount on Record Nov 2002 1 Name on Record AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
$16,000Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 Amount on Record Feb 2003 1 Name on Record AssessorUpdated Sep 2023
Last Sale Tax Bill Prior Sale Owner Records
$16,000Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$16,000Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$27,500Jun 2010 Amount on Record Aug 2003 1 Name on Record AssessorUpdated Apr 2026
Last Sale Tax Bill Prior Sale Owner Records
$20,000Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$20,000Jan 1996 1 Name on Record Owner Occupied AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$18,500Jan 1996 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$25,000Apr 2002 1 Name on Record Owner Occupied AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—May 2016 1 Name on Record AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—Oct 2004 1 Name on Record AssessorUpdated Aug 2026

8047 Windward Key Dr

4.5 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Sep 2013 $6,7422025 Amount on Record Jul 2002 2 Names on Record AssessorUpdated Jul 2026

8048 Windward Key Dr

4.5 ba · 2,207 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Feb 2014 $6,7252025 Amount on Record Jan 2010 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

8049 Windward Key Dr

3 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Jun 2023 $5,7092023 Amount on Record Apr 2002 2 Names on Record Assessor + 1 DocumentUpdated Sep 2023

8050 Windward Key Dr

2.5 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Dec 2016 $6,5772025 Amount on Record Jul 2004 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

8051 Windward Key Dr

4.5 ba · 2,277 sqft · built 2002 · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$725,000Apr 2022 $7,4562025 Amount on Record Apr 2002 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

8052 Windward Key Dr

2.5 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Apr 2003 $6,6042025 Amount on Record Jun 2002 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

8053 Windward Key Dr

2.5 ba · 2,285 sqft · built 2001 · 0.065 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,996Jun 2001 $8,0522025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

8054 Windward Key Dr

2.5 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,135Apr 2002 $6,5772025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

8055 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,009May 2001 $6,7542025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

8056 Windward Key Dr

2.5 ba · 2,200 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$775,000Aug 2024 $6,5032024 Amount on Record Jan 2018 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

8057 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
$334,851Apr 2001 $6,7472025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

8058 Windward Key Dr

4.5 ba · 2,186 sqft · built 2002 · 0.043 acres

Last Sale Tax Bill Prior Sale Owner Records
$555,000Jan 2012 $6,6562025 Amount on Record Aug 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

8059 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
$310,000Apr 2001 $6,7472025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

8060 Windward Key Dr

2.5 ba · 2,277 sqft · built 2002 · 0.072 acres

Last Sale Tax Bill Prior Sale Owner Records
$392,466Apr 2002 $7,1172025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

8061 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2002 $6,7472025 —Apr 2001 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

8062 Windward Key Dr

3.5 ba · 2,303 sqft · built 1989 · 0.077 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Jun 1993 $5,6832025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

8063 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,000Apr 2001 $6,7472025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

8064 Windward Key Dr

4 ba · 2,198 sqft · built 1989 · 0.046 acres

Last Sale Tax Bill Prior Sale Owner Records
$530,000Oct 2004 $4,4312023 Amount on Record Oct 1995 1 Name on Record Owner Occupied AssessorUpdated Sep 2023

8065 Windward Key Dr

5 ba · 2,206 sqft · built 2001 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$887,000Oct 2025 $5,8932023 Amount on Record Oct 2021 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Oct 2025

8066 Windward Key Dr

5 ba · 2,198 sqft · built 1989 · 0.046 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Jan 2018 $4,4332023 Amount on Record Jun 2010 2 Names on Record Owner Occupied AssessorUpdated Sep 2023

8067 Windward Key Dr

2.5 ba · 2,206 sqft · built 2001 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2000 $6,7472025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

8068 Windward Key Dr

4 ba · 2,198 sqft · built 1989 · 0.046 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Apr 2018 $5,2602025 Amount on Record Mar 1993 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

8069 Windward Key Dr

5 ba · 2,206 sqft · built 2001 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Jun 2021 $5,9762023 Amount on Record Jun 2018 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

8070 Windward Key Dr

3.5 ba · 2,186 sqft · built 1989 · 0.046 acres

Last Sale Tax Bill Prior Sale Owner Records
$565,000Nov 2020 $5,5202025 Amount on Record Sep 2010 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

8071 Windward Key Dr

4.5 ba · 2,285 sqft · built 2001 · 0.062 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Sep 2015 $7,3972025 Amount on Record Mar 2001 2 Names on Record AssessorUpdated Jun 2026

8072 Windward Key Dr

4 ba · 2,198 sqft · built 1989 · 0.045 acres

Last Sale Tax Bill Prior Sale Owner Records
$207,000Aug 1998 $4,4312023 2 Names on Record Owner Occupied AssessorUpdated Sep 2023

8073 Windward Key Dr

5 ba · 2,299 sqft · built 1997 · 0.074 acres

Last Sale Tax Bill Prior Sale Owner Records
$620,000Jun 2015 $7,0662023 Amount on Record Nov 1997 2 Names on Record AssessorUpdated Sep 2023

8074 Windward Key Dr

3.5 ba · 2,186 sqft · built 1989 · 0.042 acres

Last Sale Tax Bill Prior Sale Owner Records
$835,000Jun 2026 $5,0472025 Amount on Record Aug 2017 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

8075 Windward Key Dr

2.5 ba · 2,190 sqft · built 1997 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$780,000Jan 2006 $6,4712025 —Oct 2002 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

8076 Windward Key Dr

3.5 ba · 2,190 sqft · built 1989 · 0.037 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Oct 2005 $5,0772025 2 Names on Record AssessorUpdated May 2026

8077 Windward Key Dr

5 ba · 2,178 sqft · built 1997 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000Sep 2011 $5,7242023 Amount on Record Dec 2002 2 Names on Record Owner Occupied AssessorUpdated Sep 2023

8078 Windward Key Dr

4.5 ba · 2,214 sqft · built 1989 · 0.037 acres

Last Sale Tax Bill Prior Sale Owner Records
$469,900May 2018 $5,5032025 Amount on Record Jun 2007 2 Names on Record Owner Occupied Assessor + 7 DocumentsUpdated Aug 2026

8079 Windward Key Dr

4.5 ba · 2,198 sqft · built 1997 · 0.044 acres

Last Sale Tax Bill Prior Sale Owner Records
$589,000Nov 2018 $6,8272025 Amount on Record May 2007 2 Names on Record Assessor + 4 DocumentsUpdated Apr 2026

8080 Windward Key Dr

4 ba · 2,303 sqft · built 1989 · 0.068 acres

Last Sale Tax Bill Prior Sale Owner Records
$594,000Aug 2007 $5,0122023 Amount on Record May 2006 1 Name on Record AssessorUpdated Sep 2023

8081 Windward Key Dr

3 ba · 2,198 sqft · built 1997 · 0.044 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Nov 2000 $5,8052023 Amount on Record Apr 1998 2 Names on Record Owner Occupied AssessorUpdated Sep 2023

8082 Windward Key Dr

3.5 ba · 2,303 sqft · built 1988 · 0.063 acres

Last Sale Tax Bill Prior Sale Owner Records
$286,800Sep 1990 $5,5052025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

8083 Windward Key Dr

2.5 ba · 2,186 sqft · built 1997 · 0.042 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2006 $6,6832025 Amount on Record Jan 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

8084 Windward Key Dr

4.5 ba · 2,198 sqft · built 1988 · 0.042 acres

Last Sale Tax Bill Prior Sale Owner Records
$610,000Nov 2023 $5,1222025 Amount on Record Jul 2013 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

8085 Windward Key Dr

5 ba · 2,321 sqft · built 1997 · 0.067 acres

Last Sale Tax Bill Prior Sale Owner Records
$825,000Feb 2007 $6,3192023 Amount on Record Sep 1997 2 Names on Record Owner Occupied AssessorUpdated Sep 2023

8086 Windward Key Dr

5 ba · 2,198 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$585,000Mar 2022 $4,8622023 Amount on Record Aug 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

8087 Windward Key Dr

4.5 ba · 2,303 sqft · built 1988 · 0.068 acres

Last Sale Tax Bill Prior Sale Owner Records
$685,000Oct 2020 $7,4652025 Amount on Record Jan 2003 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

8088 Windward Key Dr

3.5 ba · 2,186 sqft · built 1988 · 0.045 acres

Last Sale Tax Bill Prior Sale Owner Records
$493,000Apr 2009 $5,2222025 Amount on Record Oct 2003 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

8089 Windward Key Dr

4 ba · 2,186 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$540,000Mar 2020 $5,6902023 Amount on Record Aug 2000 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

8090 Windward Key Dr

3.5 ba · 2,198 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$420,000Jun 2008 $5,2182025 Amount on Record — 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

8091 Windward Key Dr

5 ba · 2,198 sqft · built 1988 · 0.045 acres

Last Sale Tax Bill Prior Sale Owner Records
$585,000Aug 2014 $6,0942023 1 Name on Record AssessorUpdated Sep 2023

8092 Windward Key Dr

3.5 ba · 2,186 sqft · built 1988 · 0.042 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Sep 2020 $5,1892025 Amount on Record Aug 2015 2 Names on Record Assessor + 4 DocumentsUpdated Apr 2026

8093 Windward Key Dr

4.5 ba · 2,190 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$535,000Jun 2017 $6,6152025 —May 2014 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

8094 Windward Key Dr

5 ba · 2,190 sqft · built 1988 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Jul 2014 Amount on Record Oct 2006 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2023

8095 Windward Key Dr

4.5 ba · 2,186 sqft · built 1988 · 0.044 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Jun 2019 $6,8712025 Amount on Record Sep 2017 1 Name on Record Owner Occupied Assessor + 6 DocumentsUpdated Apr 2026

8096 Windward Key Dr

5 ba · 2,186 sqft · built 1988 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$449,900Jun 2018 $4,7422023 Amount on Record Nov 1999 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2023

8097 Windward Key Dr

4.5 ba · 2,303 sqft · built 1988 · 0.063 acres

Last Sale Tax Bill Prior Sale Owner Records
$635,000Oct 2015 $7,6252025 Amount on Record Jun 2006 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

8098 Windward Key Dr

5 ba · 2,303 sqft · built 1988 · 0.069 acres

Last Sale Tax Bill Prior Sale Owner Records
$349,900Mar 2015 $4,5662023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2023

8175 Windward Key Dr

4 ba · 2,291 sqft · built 1988 · 0.068 acres

Last Sale Tax Bill Prior Sale Owner Records
$254,000Aug 1998 $5,6752023 2 Names on Record AssessorUpdated Sep 2023

8177 Windward Key Dr

3.5 ba · 2,190 sqft · built 1988 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$677,500Jun 2005 $6,3192025 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

8179 Windward Key Dr

4.5 ba · 2,190 sqft · built 1988 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$809,500Jul 2024 $6,5262025 Amount on Record Feb 2013 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

8181 Windward Key Dr

4.5 ba · 2,186 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$647,500Sep 2020 $6,9502025 Amount on Record Jun 2014 2 Names on Record Assessor + 3 DocumentsUpdated Apr 2026

8183 Windward Key Dr

5 ba · 2,190 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Mar 2013 $6,5622025 —Oct 2006 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

8185 Windward Key Dr

4.5 ba · 2,251 sqft · built 1988 · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$650,000Jun 2019 $7,2552025 Amount on Record May 2010 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

8187 Windward Key Dr

4 ba · 2,303 sqft · built 1988 · 0.065 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Oct 2025 $6,0342023 Amount on Record Feb 1999 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

8189 Windward Key Dr

3.5 ba · 2,186 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Aug 2024 $6,4892025 —Oct 2005 1 Name on Record AssessorUpdated Apr 2026

8191 Windward Key Dr

3.5 ba · 2,190 sqft · built 1988 · 0.039 acres

Last Sale Tax Bill Prior Sale Owner Records
$318,500May 2011 $6,4932025 1 Name on Record AssessorUpdated Apr 2026

8193 Windward Key Dr

3.5 ba · 2,198 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2000 $6,5052025 Amount on Record Jul 1988 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

8195 Windward Key Dr

5 ba · 2,186 sqft · built 1988 · 0.038 acres

Last Sale Tax Bill Prior Sale Owner Records
$745,000Sep 2022 $5,6602023 Amount on Record May 2017 3 Names on Record Assessor + 2 DocumentsUpdated Sep 2023

8197 Windward Key Dr

4 ba · 2,190 sqft · built 1988 · 0.04 acres

Last Sale Tax Bill Prior Sale Owner Records
$630,000Feb 2023 $5,6472023 Amount on Record Aug 2005 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

8199 Windward Key Dr

4.5 ba · 2,303 sqft · built 1988 · 0.065 acres

Last Sale Tax Bill Prior Sale Owner Records
$587,500Dec 2018 $7,3452025 Amount on Record Feb 2017 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

Wildfire Risk on Windward Key Dr

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

Wildfire RiskLow
this street's cells rank above 11% of the US · above 24% of Maryland
Wildfire LikelihoodLess than 1 in 10,000 per year
ExposureIndirect
0 of 2 cells directly exposed

Property Records in Nearby Streets