Cypress Dr, Big Pine Key, FL Property Records

Monroe County property records for 15 addresses on Cypress Dr, Big Pine Key, FL · Last verified August 2026

Cypress Dr Highlights

Properties 15
Median Sale Price $465,000
Deeds and Mortgages on File 29
Median Price per Sqft $430
Owner Occupied 67%
Median Annual Tax Bill $4,876
Median Year Built 1985
Median Ownership Tenure 8 years

Properties on Cypress Dr

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

29207 Cypress Dr

2 bd · 2 ba · 1,248 sqft · 0.169 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$130,000Jan 1994 $2,2752024 Amount on Record Aug 1991 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

29231 Cypress Dr

3 bd · 2 ba · 2,096 sqft · 0.275 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$14,000May 1986 $7,3412024 Amount on Record Mar 1982 1 Name on Record AssessorUpdated Apr 2026

29255 Cypress Dr

2 bd · 2 ba · 912 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$426,000Mar 2019 $5,2502024 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Dec 2025

29267 Cypress Dr

3 bd · 2 ba · 1,048 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$380,000Mar 2017 $3,6332024 Amount on Record Oct 1997 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

29279 Cypress Dr

2 bd · 2 ba · 1,056 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$130,000Apr 1996 $1,0582024 2 Names on Record Owner Occupied AssessorUpdated Dec 2025

29287 Cypress Dr

2 bd · 2 ba · 1,896 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$100Oct 2018 $2,3942024 Amount on Record Feb 1977 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

29295 Cypress Dr

2 bd · 2.5 ba · 1,456 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$4,500Feb 1974 $5,7212025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

29321 Cypress Dr

2 bd · 1 ba · 1,064 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jul 2018 $2,9022024 Amount on Record Apr 2008 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

29331 Cypress Dr

2 bd · 2 ba · 1,080 sqft · 0.068 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Oct 2021 $5482024 Amount on Record Oct 2018 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Dec 2025

29333 Cypress Dr

2 bd · 1.5 ba · 1,251 sqft · 0.068 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$415,000Sep 2021 $3,8782024 Amount on Record Oct 2018 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

29345 Cypress Dr

2 bd · 2 ba · 1,152 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$825,000Aug 2023 $6,6802024 Amount on Record Apr 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Dec 2025

29357 Cypress Dr

2 bd · 2 ba · 960 sqft · 0.137 acres

Last Sale Tax Bill Prior Sale Owner Records
$267,500Oct 2009 $5,3732024 Amount on Record Jul 1999 1 Name on Record AssessorUpdated Dec 2025

29367 Cypress Dr

2 bd · 4 ba · 1,617 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$336,500Jan 2016 $5,9842024 Amount on Record Dec 1995 2 Names on Record AssessorUpdated Dec 2025

29381 Cypress Dr

2 bd · 2 ba · 816 sqft · 0.137 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$765,000Jun 2023 $5,8642024 Amount on Record Dec 2019 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Dec 2025

29393 Cypress Dr

3 bd · 2 ba · 1,700 sqft · 0.137 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$690,000Jun 2025 $4,8762024 Amount on Record Apr 2017 2 Names on Record Assessor + 3 DocumentsUpdated Apr 2026

Wildfire Risk on Cypress Dr

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

Wildfire RiskLow
this street's cells rank at the 4th percentile of exposed land nationally · 3rd in Florida
Wildfire LikelihoodLow — less than 1 in 10,000 per year
ExposureDirect
1 of 2 cells directly exposed · 1 adjoin burnable vegetation

Property Records in Nearby Streets