Masthead Dr, Osprey, FL Property Records

Sarasota County property records for 7 addresses on Masthead Dr, Osprey, FL · Last verified June 2026

Masthead Dr Highlights

Properties 7
Median Sale Price $600,000
Deeds and Mortgages on File 17
Median Price per Sqft $225
Owner Occupied 86%
Median Annual Tax Bill $27,727
Median Year Built 2020
Median Ownership Tenure 7 years

Properties on Masthead Dr

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

14401 Masthead Dr

3 bd · 3.5 ba · 2,665 sqft · 0.441 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$600,000Dec 2016 $8742025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Jun 2026

14405 Masthead Dr

3 bd · 4 ba · 2,796 sqft · 0.468 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,650,000May 2021 $26,8672025 Amount on Record May 2018 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jan 2026

14409 Masthead Dr

4 bd · 5 ba · 3,434 sqft · 0.447 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$600,000Oct 2017 $34,5962025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

14413 Masthead Dr

3 bd · 4 ba · 2,651 sqft · 0.392 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,700,000Feb 2020 $28,3932025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jan 2026

14417 Masthead Dr

4 bd · 4 ba · 2,292 sqft · 0.381 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$550,000Mar 2017 $27,7272025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

14421 Masthead Dr

3 bd · 5 ba · 2,757 sqft · 0.384 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$547,500Feb 2019 $29,2062025 2 Names on Record Assessor + 2 DocumentsUpdated Jan 2026

14425 Masthead Dr

3 bd · 3 ba · 2,731 sqft · 0.454 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$500,000Mar 2019 $21,8292025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

Wildfire Risk on Masthead 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 of burnable land

Property Records in Nearby Streets