Flagship Dr, Summerland Key, FL Property Records

Monroe County property records for 36 addresses on Flagship Dr, Summerland Key, FL · Last verified August 2026

Flagship Dr Highlights

Properties 36
Median Sale Price $2,000,000
Deeds and Mortgages on File 42
Median Price per Sqft $868
Owner Occupied 50%
Median Annual Tax Bill $12,588
Median Year Built 1990
Median Ownership Tenure 10 years

Properties on Flagship Dr

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

821 Flagship Dr

3 bd · 3 ba · 2,995 sqft · built 1973 · 0.346 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,009,400Mar 2009 $23,5552025 Amount on Record May 2006 1 Name on Record AssessorUpdated Jul 2026

822 Flagship Dr

5 bd · 6 ba · 4,116 sqft · built 1990 · 0.357 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000Feb 2011 $27,5262024 Amount on Record Jun 1999 2 Names on Record AssessorUpdated Dec 2025

832 Flagship Dr

5 bd · 6 ba · 2,292 sqft · built 1990 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,9042024 1 Name on Record AssessorUpdated Dec 2025

841 Flagship Dr

2 bd · 2 ba · 1,152 sqft · built 1984 · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,000Feb 1977 $3,3172024 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

861 Flagship Dr

3 bd · 3 ba · 1,682 sqft · built 1981 · 0.228 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,499,000Nov 2021 $14,1642024 Amount on Record Jul 2017 3 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

914 Flagship Dr

0.206 acres

Last Sale Tax Bill Prior Sale Owner Records
$160,000Jun 1990 $9,4582024 Amount on Record Jun 1987 2 Names on Record AssessorUpdated Apr 2026

923 Flagship Dr

5 bd · 5.5 ba · 3,782 sqft · built 2007 · 0.228 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Dec 2019 $11,9702024 —Sep 2019 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

924 Flagship Dr

3 bd · 2.5 ba · 2,811 sqft · built 1990 · 0.214 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000Dec 2013 $36,2362024 Amount on Record Mar 1989 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

933 Flagship Dr

3 bd · 2 ba · 1,597 sqft · built 1997 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$690,000Nov 2015 $11,6422024 —Aug 2006 1 Name on Record Assessor + 1 DocumentUpdated Dec 2025

934 Flagship Dr

3 bd · 4 ba · 3,354 sqft · built 1995 · 0.241 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,300,000Dec 2004 $12,0352024 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

943 Flagship Dr

3 bd · 3 ba · 2,880 sqft · built 2001 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Jul 2025 $17,9922024 Amount on Record May 2022 2 Names on Record Assessor + 5 DocumentsUpdated Apr 2026

953 Flagship Dr

2 bd · 2 ba · 2,028 sqft · built 1985 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$899,000Apr 2019 $6,9932024 Amount on Record Jan 2018 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

954 Flagship Dr

2 bd · 2 ba · 2,377 sqft · built 1991 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Apr 2019 $30,6452024 Amount on Record Jan 2018 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

974 Flagship Dr

3 bd · 4 ba · 5,608 sqft · built 2001 · 0.438 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,550,000Feb 2006 $30,6862024 Amount on Record Dec 2004 2 Names on Record AssessorUpdated Dec 2025

999 Flagship Dr

3 bd · 4 ba · 3,590 sqft · built 2023 · 0.462 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,000,000May 2024 $23,0422024 Amount on Record Aug 2017 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

1005 Flagship Dr

3 bd · 3 ba · 2,750 sqft · built 2002 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$830,000Jun 2011 $13,4582024 Amount on Record May 2002 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

1015 Flagship Dr

3 bd · 2 ba · 3,139 sqft · built 2010 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Apr 2019 $10,2892024 Amount on Record Nov 2010 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

1016 Flagship Dr

3 bd · 3 ba · 1,750 sqft · built 1979 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$567,500Jul 1998 $7,4962024 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

1025 Flagship Dr

3 bd · 3 ba · 2,540 sqft · built 1994 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Feb 1993 $8,1992024 —Oct 1990 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

1026 Flagship Dr

2 bd · 2 ba · 2,054 sqft · built 1979 · 0.22 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Apr 1990 $16,2332024 Amount on Record Feb 1975 2 Names on Record AssessorUpdated Apr 2026

1035 Flagship Dr

3 bd · 3 ba · 1,800 sqft · built 2000 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$770,000Feb 2016 $6,9052024 —Nov 2009 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

1036 Flagship Dr

3 bd · 3 ba · 1,200 sqft · built 1974 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$847,000May 2015 $8,3752024 Amount on Record Feb 2003 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

1045 Flagship Dr

3 bd · 2 ba · 2,536 sqft · built 1987 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$820,000Jul 2017 $7,0522024 Amount on Record Jun 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1046 Flagship Dr

3 bd · 3 ba · 3,956 sqft · built 2001 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Aug 2019 $25,3002025 Amount on Record — 2 Names on Record Assessor + 2 DocumentsUpdated Jul 2026

1055 Flagship Dr

3 bd · 2 ba · 2,216 sqft · built 1987 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Jan 2020 $5,9732024 Amount on Record Oct 1987 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

1056 Flagship Dr

3 bd · 2.5 ba · 1,698 sqft · built 1978 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,100,000Feb 2016 $9,3542024 Amount on Record Aug 2001 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

1065 Flagship Dr

3 bd · 2 ba · 1,838 sqft · built 1976 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2010 $9,6372024 Amount on Record — 1 Name on Record AssessorUpdated Apr 2026

1066 Flagship Dr

4 bd · 3 ba · 3,442 sqft · built 1973 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Mar 2016 $24,4332024 Amount on Record May 1995 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

1076 Flagship Dr

2 bd · 2 ba · 1,484 sqft · built 1988 · 0.257 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Oct 2021 $21,9352024 Amount on Record Apr 1995 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

1086 Flagship Dr

4 bd · 3 ba · 3,155 sqft · built 2018 · 0.192 acres

Last Sale Tax Bill Prior Sale Owner Records
$787,500Jun 2003 $10,3402024 —Dec 2001 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

1122 Flagship Dr

3 bd · 3 ba · 2,047 sqft · built 1987 · 0.293 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,200,000May 2021 $23,8242024 Amount on Record Jun 2016 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

1127 Flagship Dr

2 bd · 2.5 ba · 2,741 sqft · built 1993 · 0.231 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,130,000Jul 2020 $12,5882024 Amount on Record Dec 1981 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

1142 Flagship Dr

2 bd · 3 ba · 1,840 sqft · built 1979 · 0.234 acres

Last Sale Tax Bill Prior Sale Owner Records
$287,500Mar 1987 $6,5482024 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

1147 Flagship Dr

3 bd · 3 ba · 2,058 sqft · built 1997 · 0.225 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,725,000Mar 2026 $13,8412024 Amount on Record Apr 2015 2 Names on Record Assessor + 1 DocumentUpdated Apr 2026

1162 Flagship Dr

2 bd · 2 ba · 2,060 sqft · built 1980 · 0.243 acres

Last Sale Tax Bill Prior Sale Owner Records
$100Sep 2013 $17,6902025 Amount on Record Oct 1980 1 Name on Record Assessor + 3 DocumentsUpdated May 2026

1167 Flagship Dr

3 bd · 2 ba · 1,200 sqft · built 1979 · 0.206 acres

Last Sale Tax Bill Prior Sale Owner Records
$860,000Jan 2021 $10,7832024 Amount on Record Feb 2015 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

Wildfire Risk on Flagship Dr

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

Wildfire RiskNot rated
no burnable land in reach
Wildfire LikelihoodNegligible
ExposureNone
beyond ember reach

Property Records in Nearby Streets