Roosevelt Dr, Key West, FL Property Records

Monroe County property records for 11 addresses on Roosevelt Dr, Key West, FL · Last verified August 2026

Roosevelt Dr Highlights

Properties 11
Median Sale Price $710,000
Deeds and Mortgages on File 20
Median Price per Sqft $333
Owner Occupied 27%
Median Annual Tax Bill $6,879
Median Year Built 1950
Median Ownership Tenure 6 years

Properties on Roosevelt Dr

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

1908 Roosevelt Dr

6 bd · 5 ba · 2,124 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Aug 2022 $9,2762024 Amount on Record Mar 2017 2 Names on Record Assessor + 4 DocumentsUpdated Apr 2026

1909 Roosevelt Dr

8 bd · 4 ba · 3,000 sqft · 0.172 acres

Last Sale Tax Bill Prior Sale Owner Records
$710,000Jun 2021 $9,5632024 —Nov 2016 1 Name on Record Assessor + 3 DocumentsUpdated Apr 2026

1912 Roosevelt Dr

4 bd · 3 ba · 1,500 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$310,000Mar 2013 $6,8792024 Amount on Record Feb 1974 2 Names on Record AssessorUpdated Apr 2026

1916 Roosevelt Dr

8 bd · 4 ba · 3,000 sqft · 0.16 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000Apr 2022 $10,4142024 Amount on Record Feb 1974 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

2008 Roosevelt Dr

4 bd · 2 ba · 1,500 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,000Oct 1983 $6,7222024 1 Name on Record AssessorUpdated Dec 2025

2009 Roosevelt Dr

2 bd · 2 ba · 1,110 sqft · 0.086 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$565,000Jul 2020 $4,9962025 Amount on Record Oct 2001 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

2010 Roosevelt Dr

2 bd · 2 ba · 1,873 sqft · 0.079 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Jun 2019 $6,5882024 Amount on Record Oct 2014 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

2012 Roosevelt Dr

2 bd · 2 ba · 1,515 sqft · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Feb 2011 $2,9322025 Amount on Record Mar 2002 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

2013 Roosevelt Dr

5 bd · 3 ba · 2,200 sqft · 0.209 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Apr 2021 $8,0532024 —Sep 2016 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

2016 Roosevelt Dr

7 bd · 5 ba · 2,957 sqft · 0.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$592,000Oct 2020 $9,9722025 Amount on Record Sep 2006 1 Name on Record Assessor + 3 DocumentsUpdated Jun 2026

2017 Roosevelt Dr

4 bd · 2 ba · 1,500 sqft · 0.141 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$340,000May 2014 $6,5842024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

Wildfire Risk on Roosevelt 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