Gulfside Dr, Islamorada, FL Property Records

Monroe County property records for 12 addresses on Gulfside Dr, Islamorada, FL · Last verified July 2026

Gulfside Dr Highlights

Properties 12
Median Sale Price $2,400,000
Deeds and Mortgages on File 18
Median Price per Sqft $914
Owner Occupied 42%
Median Annual Tax Bill $26,382
Median Year Built 1994
Median Ownership Tenure 7 years

Properties on Gulfside Dr

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

100 Gulfside Dr

3 bd · 3 ba · 2,983 sqft · built 1985 · 0.22 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,400,000Mar 2021 $28,7912024 Amount on Record Oct 1997 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

104 Gulfside Dr

4 bd · 4 ba · 2,760 sqft · built 2004 · 0.286 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Jun 2020 $27,9332024 Amount on Record Sep 2005 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

108 Gulfside Dr

3 bd · 3 ba · 1,332 sqft · built 1998 · 0.293 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,325,000Oct 2018 $21,0932024 Amount on Record Mar 2004 2 Owners on Record Assessor + 3 DocumentsUpdated Dec 2025

116 Gulfside Dr

3 bd · 2 ba · 2,158 sqft · built 1987 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,600,000Jul 2025 $27,7672024 Amount on Record Aug 2022 2 Owners on Record Assessor + 5 DocumentsUpdated Apr 2026

120 Gulfside Dr

3 bd · 3 ba · 3,475 sqft · built 1989 · 0.202 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,150,000Apr 2009 $21,5042024 Amount on Record Feb 1996 Owner on Record AssessorUpdated Apr 2026

124 Gulfside Dr

2 bd · 2 ba · 2,468 sqft · built 1999 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,250,000Apr 2014 $15,1392024 Amount on Record Mar 2011 Owner on Record Owner Occupied AssessorUpdated Dec 2025

126 Gulfside Dr

3 bd · 2 ba · 3,067 sqft · built 1998 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,650,000Sep 2004 $8,3122024 Amount on Record Feb 2000 2 Owners on Record Owner Occupied AssessorUpdated Dec 2025

128 Gulfside Dr

5 bd · 3 ba · 3,591 sqft · built 1989 · 0.325 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,500,000Oct 2020 $26,6052024 —Oct 2013 2 Owners on Record Assessor + 4 DocumentsUpdated Dec 2025

132 Gulfside Dr

3 bd · 2 ba · 2,132 sqft · built 1988 · 0.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,950,000May 2019 $25,6202024 Amount on Record Dec 2008 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

140 Gulfside Dr

3 bd · 4 ba · 2,973 sqft · built 1992 · 0.738 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Jan 2000 $10,3662024 Owner on Record Owner Occupied AssessorUpdated Dec 2025

148 Gulfside Dr

3 bd · 3 ba · 1,763 sqft · built 1994 · 0.301 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,500,000Jul 2023 $33,0332024 Amount on Record Mar 2018 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

150 Gulfside Dr

3 bd · 3 ba · 2,796 sqft · built 1996 · 0.672 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2007 $26,3822024 Amount on Record Dec 1994 Owner on Record AssessorUpdated Dec 2025

Property Records in Nearby Streets