Jolly Roger Dr, Key Largo, FL Property Records

Monroe County property records for 30 addresses on Jolly Roger Dr, Key Largo, FL · Last verified October 2026

Jolly Roger Dr Highlights

Properties 30
Median Sale Price $1,075,000
Deeds and Mortgages on File 29
Median Price per Sqft $708
Owner Occupied 47%
Median Annual Tax Bill $5,720
Median Year Built 1973
Median Ownership Tenure 8 years

Properties on Jolly Roger Dr

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

19 Jolly Roger Dr

2 bd · 1 ba · 1,010 sqft · built 1959 · 0.358 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,5182024 Owner on Record Assessor + 1 DocumentUpdated Apr 2026

25 Jolly Roger Dr

3 bd · 3 ba · 942 sqft · built 1976 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Feb 1990 $5,9392024 Owner on Record Owner Occupied AssessorUpdated Dec 2025

29 Jolly Roger Dr

3 bd · 3 ba · 1,520 sqft · built 1979 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Feb 2017 $2,8892024 Amount on Record Apr 1999 Owner on Record Owner Occupied AssessorUpdated Dec 2025

33 Jolly Roger Dr

2 bd · 1 ba · 793 sqft · built 1957 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$575,000May 2018 $5,4962024 Amount on Record Dec 2000 2 Owners on Record Assessor + 3 DocumentsUpdated Apr 2026

35 Jolly Roger Dr

3 bd · 2 ba · 1,162 sqft · built 2022 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$107,000Aug 1992 $7632023 Amount on Record Feb 1978 Owner on Record AssessorUpdated Aug 2026

37 Jolly Roger Dr

2 bd · 1 ba · 1,020 sqft · built 1971 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Aug 2019 $5,8422024 Amount on Record Feb 1969 Owner on Record Assessor + 1 DocumentUpdated Sep 2026

41 Jolly Roger Dr

4 bd · 3 ba · 1,376 sqft · built 1972 · 0.19 acres

Last Sale Tax Bill Prior Sale Owner Records
$630,000Apr 2014 $8,3492024 Amount on Record May 2001 Owner on Record AssessorUpdated Dec 2025

43 Jolly Roger Dr

3 bd · 2 ba · 3,090 sqft · built 1973 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Jan 2019 $8,3082024 Amount on Record Jun 1989 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

118 Jolly Roger Dr

1 bd · 1 ba · 500 sqft · built 1970 · 0.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$354,000Jan 2021 $3,5152024 Amount on Record Aug 2000 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

121 Jolly Roger Dr

2 bd · 2 ba · 1,080 sqft · built 1973 · 0.227 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,000Jul 1988 $2,9932024 Owner on Record Owner Occupied AssessorUpdated Dec 2025

123 Jolly Roger Dr

2 bd · 2 ba · 1,408 sqft · built 1969 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Dec 2010 $5,8722024 —Jun 2010 2 Owners on Record AssessorUpdated Sep 2026

125 Jolly Roger Dr

2 bd · 2 ba · 1,188 sqft · built 2000 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$420,000Jun 2013 $8,1842024 Amount on Record Feb 1996 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

127 Jolly Roger Dr

1 bd · 1 ba · 1,272 sqft · built 1970 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,500Feb 2013 $5,4022024 —Jan 2007 2 Owners on Record AssessorUpdated Sep 2026

210 Jolly Roger Dr

2 bd · 2 ba · 1,485 sqft · built 2004 · 0.373 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Jul 1999 $5,7162024 Amount on Record Jan 1999 Owner on Record Owner Occupied AssessorUpdated Apr 2026

212 Jolly Roger Dr

2 bd · 1 ba · 816 sqft · built 1960 · 0.233 acres

Last Sale Tax Bill Prior Sale Owner Records
$520,000Sep 2021 $5,5642024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

215 Jolly Roger Dr

2 bd · 2 ba · 1,200 sqft · built 1984 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,075,000Oct 2021 $7,6182024 Owner on Record Assessor + 1 DocumentUpdated Dec 2025

219 Jolly Roger Dr

2 bd · 2.5 ba · 1,354 sqft · built 1998 · 0.121 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jul 1998 $2,8402024 Amount on Record Jan 1996 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

220 Jolly Roger Dr

3 bd · 2 ba · 2,138 sqft · built 1956 · 0.252 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,2132024 Owner on Record Owner Occupied AssessorUpdated Dec 2025

221 Jolly Roger Dr

2 bd · 1 ba · 768 sqft · built 1964 · 0.118 acres

Last Sale Tax Bill Prior Sale Owner Records
$435,000Mar 2018 $5,5452024 Amount on Record Apr 1989 2 Owners on Record Assessor + 2 DocumentsUpdated Aug 2026

222 Jolly Roger Dr

3 bd · 3.5 ba · 2,400 sqft · built 2021 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Oct 2019 $10,6632025 Amount on Record Sep 2005 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

223 Jolly Roger Dr

0.115 acres

Last Sale Tax Bill Prior Sale Owner Records
$345,000Aug 2021 $3,5742024 —Jan 2016 Owner on Record Assessor + 3 DocumentsUpdated Dec 2025

225 Jolly Roger Dr

3 bd · 3 ba · 1,800 sqft · built 1974 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$80,000Aug 2019 $5,3062024 —Jan 1998 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

227 Jolly Roger Dr

2 bd · 2 ba · 1,488 sqft · built 1986 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Nov 1988 $5,7202024 Amount on Record Nov 1986 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

228 Jolly Roger Dr

4 bd · 2 ba · 2,421 sqft · built 1972 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$900,000Jul 2017 $11,2122024 Amount on Record Mar 2013 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

230 Jolly Roger Dr

2 bd · 2 ba · 1,841 sqft · built 1958 · 0.154 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Jun 2026 $6,6962025 Amount on Record Sep 2005 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

233 Jolly Roger Dr

2 bd · 2 ba · 1,056 sqft · built 2024 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5122024 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

237 Jolly Roger Dr

2 bd · 3 ba · 2,016 sqft · built 1987 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$755,000Mar 2019 $5,4342024 Amount on Record Oct 2004 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

302 Jolly Roger Dr

2 bd · 3 ba · 1,536 sqft · built 1971 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
$90,000Aug 1978 $10,9552024 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

305 Jolly Roger Dr

3 bd · 3 ba · 2,801 sqft · built 2018 · 0.191 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,475,000Mar 2025 $8,5932024 Amount on Record Aug 2015 Owner on Record AssessorUpdated Apr 2026

306 Jolly Roger Dr

3 bd · 2.5 ba · 1,666 sqft · built 1990 · 0.191 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Nov 2020 $11,5132024 Amount on Record Apr 2003 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

Property Records in Nearby Streets