Cypress Ave, Key West, FL Property Records

Monroe County property records for 22 addresses on Cypress Ave, Key West, FL · Last verified August 2026

Cypress Ave Highlights

Properties 22
Median Sale Price $1,750,000
Deeds and Mortgages on File 27
Median Price per Sqft $599
Owner Occupied 64%
Median Annual Tax Bill $10,888
Median Year Built 1984
Median Ownership Tenure 13 years

Properties on Cypress Ave

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

2 Cypress Ave

3 bd · 2 ba · 1,444 sqft · 0.144 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$40,000Nov 1983 $5,0452024 Amount on Record May 1980 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

4 Cypress Ave

4 bd · 2 ba · 1,992 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$700,000Apr 2015 $10,2852024 Amount on Record Jan 2015 1 Name on Record Owner Occupied AssessorUpdated Dec 2025

6 Cypress Ave

3 bd · 2.5 ba · 1,776 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Dec 2015 $9,8132025 Amount on Record Aug 2012 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

8 Cypress Ave

0.216 acres

Last Sale Tax Bill Prior Sale Owner Records
$649,000May 2005 $7,1582024 2 Names on Record Assessor + 1 DocumentUpdated Dec 2025

11 Cypress Ave

3 bd · 2.5 ba · 3,200 sqft · 0.361 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$3,200,000Feb 2021 $33,4652024 Amount on Record Apr 2018 1 Name on Record Assessor + 4 DocumentsUpdated Aug 2026

13 Cypress Ave

4 bd · 3 ba · 1,960 sqft · 0.164 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$103,500Apr 1999 $7,7502024 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Dec 2025

15 Cypress Ave

4 bd · 2 ba · 2,730 sqft · 0.164 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$150,000Aug 2001 $12,5562024 Amount on Record Feb 2000 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

17 Cypress Ave

4 bd · 3 ba · 2,202 sqft · 0.166 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,321,000May 2021 $15,2202024 Amount on Record Jun 2006 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

19 Cypress Ave

3 bd · 3 ba · 2,602 sqft · 0.227 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,275,000Apr 2017 $17,3802024 Amount on Record Apr 2011 2 Names on Record Assessor + 2 DocumentsUpdated Dec 2025

21 Cypress Ave

3 bd · 2 ba · 3,341 sqft · 0.256 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,750,000Jan 2022 $23,9322025 Amount on Record May 2001 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

23 Cypress Ave

3 bd · 2 ba · 2,684 sqft · 0.328 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Feb 2020 $11,8622024 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

27 Cypress Ave

3 bd · 2 ba · 1,796 sqft · 0.573 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$12,000Feb 1973 $8,5812024 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

31 Cypress Ave

3 bd · 2 ba · 3,807 sqft · 0.171 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$300,000Apr 1999 $8,7192024 Amount on Record Jan 1987 2 Names on Record Owner Occupied AssessorUpdated Apr 2026

33 Cypress Ave

4 bd · 4 ba · 4,102 sqft · 0.156 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$3,250,000Feb 2026 $20,0622024 Amount on Record Feb 2011 2 Names on Record Assessor + 1 DocumentUpdated May 2026

35 Cypress Ave

3 bd · 2 ba · 2,050 sqft · 0.156 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2002 $5,2492025 Amount on Record Mar 1997 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

37 Cypress Ave

2 bd · 1.5 ba · 1,530 sqft · 0.156 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$599,000May 2011 $9,6252024 Amount on Record Feb 1976 2 Names on Record AssessorUpdated Aug 2026

39 Cypress Ave

3 bd · 2 ba · 2,530 sqft · 0.156 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100Mar 2012 $3,9922024 Amount on Record Dec 1988 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

41 Cypress Ave

3 bd · 2.5 ba · 2,235 sqft · 0.156 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$918,750Nov 2019 $11,4472024 Amount on Record Aug 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

45 Cypress Ave

4 bd · 3 ba · 4,078 sqft · 0.313 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$699,000Aug 2013 $15,2022024 Amount on Record Jan 2006 1 Name on Record AssessorUpdated Jul 2026

46 Cypress Ave

3 bd · 3 ba · 3,892 sqft · 0.509 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,728,312Nov 2024 $28,3062024 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

47 Cypress Ave

3 bd · 2 ba · 2,021 sqft · 0.156 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$810,000Apr 2001 $7,1582024 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

49 Cypress Ave

2 bd · 2.5 ba · 2,045 sqft · 0.156 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$20,000Oct 1977 $10,8882025 1 Name on Record Assessor + 1 DocumentUpdated May 2026

Wildfire Risk on Cypress Ave

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