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Single Family ResidenceResidential
$2,850,000$1,069 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 88How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Sep 24, 2026
Last sold for $2,630,000 on Oct 15, 2026

14401 MASTHEAD DR

OSPREY, FL 34229
3
Beds
3.5
Baths
2,665 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
0.44 ac
Lot SizeThe size of the land the home sits on, from county records.
2017
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
7
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$2.9M
$2.5M low$3.2M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$2,630,000 · Oct 15, 2026

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$874 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$1,295,472 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$1,258,962
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$2,501,700

Climate Risk

Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.84 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.99%
FEMA Flood ZoneFEMA's flood zone for this address. Zones starting with A or V are high risk, and lenders usually require flood insurance there.1 percent flood zone

Scores 0–100; higher = greater projected risk.

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountySARASOTA
Lot (acres)The size of the land the home sits on, from county records.0.44
ConstructionThe main material the home's frame and walls are built from.Masonry/Concrete Masonry Units (Cmus)
FoundationWhat the home is built on, such as a concrete slab, a crawl space, or a basement.Retaining Wall
RoofThe main material covering the roof, such as asphalt shingle or tile.Metal
HeatingThe type of heating system in the home.Central
CoolingThe type of cooling or air conditioning in the home.Central
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Attached
PoolWhether the property has a pool, and what kind, such as in-ground.Yes
ViewThe type of view from the property, or another feature of the site that affects value.Bay
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Deck · 147 ft²Patio · 1,076 ft²Porch · 721 ft²

Transaction History(4)

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.

E
Laurel Nokomis SchoolA
Elementary · Grades PK–8 · 5.2 mi
H
Venice High SchoolA-
High · Grades 9–12 · 7.0 mi

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.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.62
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.84
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.18

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.86%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.32%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.6.2%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.7%
PopulationHow many people live in this area.8,568
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,085 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$94,218
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$136,167
Average tempThe average temperature here across a full year.73°F
Annual precipHow much rain and melted snow falls here in a typical year.53 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.68%

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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

14401 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.

  • Worth more than 98% of homes in Osprey 34229
  • Among the highest price per square foot in Osprey 34229
  • Bigger than 91% of homes in Sarasota County
  • Has a bigger lot than 85% of homes in Sarasota County
  • Newer than 95% of homes in Osprey 34229

What homes are worth in Osprey 34229

Each bar is how many homes fall in that price range. The marker is this home.

This home
$216K$3.1M

This home is worth more than 98% of 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.

Estimated value$2,850,000
CheaperTypical $661,918Pricier

Pricier than 98% of homes nearby

Price per ft²$1069
CheaperTypical $306Pricier

Pricier than almost all homes nearby

Living area2,665 ft²
SmallerTypical 2,190 ft²Bigger

Bigger than 74% of homes nearby

Lot size0.44 ac
SmallerTypical 0.28 acBigger

Bigger than 73% of homes nearby

Year built2017
OlderTypical 1998Newer

Newer than 95% of homes nearby

How 14401 Masthead Dr ranks against every home in each area.
MeasureThis homeOsprey 34229Sarasota County
Estimated valuepricier than$2,850,00098% of homes98% of homes
Price per ft²pricier than$1069almost all homes98% of homes
Living areabigger than2,665 ft²74% of homes91% of homes
Lot sizebigger than0.44 ac73% of homes85% of homes
Year builtnewer than201795% of homes86% of homes

About 14401 Masthead Dr

How much is 14401 Masthead Dr, Osprey, FL worth?

The TopHap Estimate for 14401 Masthead Dr, Osprey, FL is $2,850,000 as of Sep 24, 2026. The likely range is $2,515,154 to $3,184,846. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 14401 Masthead Dr, Osprey, FL last sell?

14401 Masthead Dr, Osprey, FL last sold on Oct 15, 2026 for $2,630,000, according to the county's recorded deed.

How big is 14401 Masthead Dr, Osprey, FL?

14401 Masthead Dr, Osprey, FL has 3 bedrooms, 3.5 bathrooms, 2,665 square feet of living space and a 0.44-acre lot.

When was 14401 Masthead Dr, Osprey, FL built?

14401 Masthead Dr, Osprey, FL was built in 2017, making it 9 years old. The building has 1 story.

What schools serve 14401 Masthead Dr, Osprey, FL?

14401 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 14401 Masthead Dr, Osprey, FL compare to other homes in Osprey 34229?

Among the 4,242 homes in Osprey 34229, it is worth more than 98% of them ($2,850,000 against a typical $661,918), its price per square foot is higher than almost all of them ($1069 against a typical $306), it is bigger than 74% of them (2,665 ft² against a typical 2,190 ft²), its lot is bigger than 73% of them (0.44 ac against a typical 0.28 ac) and it is newer than 95% of them (2017 against a typical 1998). Measured against all of Sarasota County, it is worth more than 98% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.

What are the property taxes on 14401 Masthead Dr, Osprey, FL?

The 2025 property tax bill for 14401 Masthead Dr, Osprey, FL was $874. The county assessed it at $1,295,472.

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