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Single Family ResidenceResidential
$1,060,469$350 / 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 86How 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 $914,000 on Dec 7, 2005

1239 WINDWARD DR

OSPREY, FL 34229
3
Beds
3
Baths
3,026 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.
0.28 ac
Lot SizeThe size of the land the home sits on, from county records.
1994
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

$1.1M
$914K low$1.2M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$914,000 · Dec 7, 2005

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$5,614 (2024)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$494,962 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$481,013
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$757,800

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.60 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.26%
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.minimal

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
Effective Year BuiltAn adjusted build year that accounts for condition and major remodels. A big renovation can make a home count as newer than it is.2004
Lot (acres)The size of the land the home sits on, from county records.0.28
ConstructionThe main material the home's frame and walls are built from.Masonry/Concrete Masonry Units (Cmus)
RoofThe main material covering the roof, such as asphalt shingle or tile.Concrete
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.Main Land
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Patio · 36 ft²Porch · 341 ft²

Transaction History(5)

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 · 4.6 mi
H
Venice High SchoolB+
High · Grades 9–12 · 6.4 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%

Owner Tools

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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

1239 Windward 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 91% of homes in Sarasota County
  • Costs more per square foot than 79% of homes in Sarasota County
  • Bigger than 96% of homes in Sarasota County
  • Has a bigger lot than 73% of homes in Sarasota County
  • Newer than 91% of homes in Southbay Yacht and Racquet Club

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
$206K$3.1M

This home is worth more than 79% 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$1,060,469
CheaperTypical $660,664Pricier

Pricier than 79% of homes nearby

Price per ft²$350
CheaperTypical $307Pricier

Pricier than 66% of homes nearby

Living area3,026 ft²
SmallerTypical 2,182 ft²Bigger

Bigger than 82% of homes nearby

Lot size0.28 ac
SmallerTypical 0.27 acBigger

Bigger than 52% of homes nearby

Year built1994
OlderTypical 1998Newer

Newer than 42% of homes nearby

How 1239 Windward Dr ranks against every home in each area.
MeasureThis homeSouthbay Yacht and Racquet ClubOsprey 34229Sarasota County
Estimated valuepricier than$1,060,46973% of homes79% of homes91% of homes
Price per ft²pricier than$35048% of homes66% of homes79% of homes
Living areabigger than3,026 ft²85% of homes82% of homes96% of homes
Lot sizebigger than0.28 ac50% of homes52% of homes73% of homes
Year builtnewer than199491% of homes42% of homes56% of homes

About 1239 Windward Dr

How much is 1239 Windward Dr, Osprey, FL worth?

The TopHap Estimate for 1239 Windward Dr, Osprey, FL is $1,060,469 as of Sep 24, 2026. The likely range is $914,465 to $1,206,473. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 1239 Windward Dr, Osprey, FL last sell?

1239 Windward Dr, Osprey, FL last sold on Dec 7, 2005 for $914,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 1239 Windward Dr, Osprey, FL?

1239 Windward Dr, Osprey, FL has 3 bedrooms, 3 bathrooms, 3,026 square feet of living space and a 0.28-acre lot.

When was 1239 Windward Dr, Osprey, FL built?

1239 Windward Dr, Osprey, FL was built in 1994, making it 32 years old. The building has 1 story.

What schools serve 1239 Windward Dr, Osprey, FL?

1239 Windward Dr, Osprey, FL is assigned to Laurel Nokomis School (elementary), rated A-; Venice High School (high), rated B+. All sit in Sarasota County School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 1239 Windward Dr, Osprey, FL compare to other homes in Osprey 34229?

Among the 4,241 homes in Osprey 34229, it is worth more than 79% of them ($1,060,469 against a typical $660,664), its price per square foot is higher than 66% of them ($350 against a typical $307), it is bigger than 82% of them (3,026 ft² against a typical 2,182 ft²), its lot is bigger than 52% of them (0.28 ac against a typical 0.27 ac) and it is newer than 42% of them (1994 against a typical 1998). Measured against all of Sarasota County, it is worth more than 91% 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 1239 Windward Dr, Osprey, FL?

The 2024 property tax bill for 1239 Windward Dr, Osprey, FL was $5,614. The county assessed it at $494,962.

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