14409 MASTHEAD DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(1)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Sarasota County School District
Neighborhood · ZIP 34229These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
How this home compares
14409 Masthead Dr measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.
- Bigger than 98% of homes in Sarasota County
- Has a bigger lot than 85% of homes in Sarasota County
- Among the newest homes in Osprey 34229
How it measures up in Osprey 34229
The dot is this home. The mark in the middle is the typical home in Osprey 34229.
Bigger than 87% of homes nearby
Bigger than 73% of homes nearby
Newer than almost all homes nearby
| Measure | This home | Osprey 34229 | Sarasota County |
|---|---|---|---|
| Living areabigger than | 3,434 ft² | 87% of homes | 98% of homes |
| Lot sizebigger than | 0.45 ac | 73% of homes | 85% of homes |
| Year builtnewer than | 2021 | almost all homes | 92% of homes |
About 14409 Masthead Dr
When did 14409 Masthead Dr, Osprey, FL last sell?
14409 Masthead Dr, Osprey, FL last sold on Oct 10, 2017 for $600,000, according to the county's recorded deed.
How big is 14409 Masthead Dr, Osprey, FL?
14409 Masthead Dr, Osprey, FL has 4 bedrooms, 5 bathrooms, 3,434 square feet of living space and a 0.45-acre lot.
When was 14409 Masthead Dr, Osprey, FL built?
14409 Masthead Dr, Osprey, FL was built in 2021, making it 5 years old. The building has 2 stories.
What schools serve 14409 Masthead Dr, Osprey, FL?
14409 Masthead Dr, Osprey, FL is assigned to Laurel Nokomis School (elementary), rated A; Venice High School (high), rated A-. All sit in Sarasota County School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 14409 Masthead Dr, Osprey, FL compare to other homes in Osprey 34229?
Among the 4,242 homes in Osprey 34229, it is bigger than 87% of them (3,434 ft² against a typical 2,190 ft²), its lot is bigger than 73% of them (0.45 ac against a typical 0.28 ac) and it is newer than almost all of them (2021 against a typical 1998). These shares are recounted nightly from the full county assessor record for each area, not from active listings.
What are the property taxes on 14409 Masthead Dr, Osprey, FL?
The 2025 property tax bill for 14409 Masthead Dr, Osprey, FL was $34,596. The county assessed it at $3,044,400.
More homes on Masthead Dr
- 14401 Masthead Dr$2.9M3 bd · 3.5 ba · 2,665 ft² · Sold $2.6M · Oct 2026
- 14405 Masthead Dr$1.9M3 bd · 4 ba · 2,796 ft² · Sold $2.7M · May 2021
- 14413 Masthead Dr$2.5M3 bd · 4 ba · 2,651 ft² · Sold $1.7M · Feb 2020
- 14425 Masthead Dr3 bd · 3 ba · 2,731 ft² · Sold $500K · Mar 2019
- 14421 Masthead Dr3 bd · 5 ba · 2,757 ft² · Sold $548K · Feb 2019
- 14417 Masthead Dr$1.5M4 bd · 4 ba · 2,292 ft² · Sold $550K · Mar 2017
Closest homes
- 14413 Masthead Dr$2.5M75 ft · 3 bd · 4 ba · 2,651 ft² · Sold $1.7M · Feb 2020
- 14405 Masthead Dr$1.9M79 ft · 3 bd · 4 ba · 2,796 ft² · Sold $2.7M · May 2021
- 14401 Masthead Dr$2.9M163 ft · 3 bd · 3.5 ba · 2,665 ft² · Sold $2.6M · Oct 2026
- 14417 Masthead Dr$1.5M170 ft · 4 bd · 4 ba · 2,292 ft² · Sold $550K · Mar 2017
- 3900 Waypoint Ave$884K214 ft · 3 bd · 3 ba · 2,343 ft² · Sold $730K · Feb 2020
- 14421 Masthead Dr244 ft · 3 bd · 5 ba · 2,757 ft² · Sold $548K · Feb 2019
- 3904 Waypoint Ave$930K272 ft · 3 bd · 3 ba · 2,344 ft² · Sold $975K · Aug 2025
- 14425 Masthead Dr323 ft · 3 bd · 3 ba · 2,731 ft² · Sold $500K · Mar 2019
More homes in Osprey 34229
- 1495 Landview Ln$760K3 bd · 2 ba · 2,474 ft² · Sold $650K · Oct 2026
- 130 Willow Bend Way$713K3 bd · 3 ba · 2,683 ft² · Sold $675K · Oct 2026
- 5100 Jessie Harbor Dr$699K2 bd · 2 ba · 2,143 ft² · Sold $615K · Oct 2026
- 701 Pine Run Dr$166K1 bd · 1 ba · 586 ft² · Sold $150K · Oct 2026
- 547 Meadow Sweet Cir$550K2 bd · 2 ba · 1,731 ft² · Sold $555K · Oct 2026
- 264 Woods Point Rd$695K2 bd · 3 ba · 2,837 ft² · Sold $665K · Oct 2026
- 1801 Highland Rd$290K2 bd · 2 ba · 1,165 ft² · Sold $256K · Oct 2026
- 401 N Point Rd$1.3M3 bd · 3 ba · 2,203 ft² · Sold $1.1M · Oct 2026
- 110 Woodland Pl$215K2 bd · 2 ba · 1,325 ft² · Sold $210K · Oct 2026
- 112 Osprey Point Dr$6.4M4 bd · 5.5 ba · 8,621 ft² · Sold $6M · Oct 2026
- 401 N Point Rd$699K3 bd · 3 ba · 2,203 ft² · Sold $575K · Oct 2026
- 329 Bay Vista Ave$399K2 bd · 2.5 ba · 1,346 ft² · Sold $398K · Oct 2026
Assigned schools
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