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Single Family ResidenceResidential
$609,325$403 / 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 83How 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 $650,000 on May 5, 2025

5239 WINDING WAY

SARASOTA, FL 34242
3
Beds
2
Baths
1,512 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.
0.21 ac
Lot SizeThe size of the land the home sits on, from county records.
1958
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

$609K
$503K low$716K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$650,000 · May 5, 2025

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$7,599 (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.$662,100 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$548,700
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$113,400
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$887,549
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$662,100

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.119 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
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.1993
Lot (acres)The size of the land the home sits on, from county records.0.21
FoundationWhat the home is built on, such as a concrete slab, a crawl space, or a basement.Mat/Raft Foundation (Slab)
RoofThe main material covering the roof, such as asphalt shingle or tile.Roll Composition (rolled Mineral Roof)
HeatingThe type of heating system in the home.Yes
CoolingThe type of cooling or air conditioning in the home.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Carport (Unspecified)
PoolWhether the property has a pool, and what kind, such as in-ground.Yes
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Patio · 1,026 ft²

Transaction History(6)

Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.

Foreclosure Filings(1)

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
Phillippi Shores Elementary SchoolA+
Elementary · Grades PK–5 · 1.5 mi
M
Brookside Middle SchoolB
Middle · Grades 6–8 · 2.3 mi
H
Sarasota High SchoolB-
High · Grades 9–12 · 3.7 mi

District: Sarasota County School District

Neighborhood · ZIP 34242These 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.157
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.92
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.11

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.41%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.35%
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.8,313
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,005 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$123,460
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$205,625
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

5239 Winding Way 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 less than 75% of homes in Sarasota 34242
  • Costs less per square foot than 97% of homes in Sarasota 34242
  • Bigger than 66% of homes in Sarasota 34242
  • Has a smaller lot than 84% of homes in Sarasota 34242
  • Older than 94% of homes in Sarasota County

What homes are worth in Sarasota 34242

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

This home
$376K$5M

This home is worth more than 25% of homes in Sarasota 34242.

How it measures up in Sarasota 34242

The dot is this home. The mark in the middle is the typical home in Sarasota 34242.

Estimated value$609,325
CheaperTypical $879,909Pricier

Pricier than 25% of homes nearby

Price per ft²$403
CheaperTypical $682Pricier

Pricier than 3% of homes nearby

Living area1,512 ft²
SmallerTypical 1,303 ft²Bigger

Bigger than 66% of homes nearby

Lot size0.21 ac
SmallerTypical 0.38 acBigger

Bigger than 16% of homes nearby

Year built1958
OlderTypical 1974Newer

Newer than 7% of homes nearby

How 5239 Winding Way ranks against every home in each area.
MeasureThis homeSarasota 34242Sarasota County
Estimated valuepricier than$609,32525% of homes75% of homes
Price per ft²pricier than$4033% of homes83% of homes
Living areabigger than1,512 ft²66% of homes47% of homes
Lot sizebigger than0.21 ac16% of homes44% of homes
Year builtnewer than19587% of homes6% of homes

About 5239 Winding Way

How much is 5239 Winding Way, Sarasota, FL worth?

The TopHap Estimate for 5239 Winding Way, Sarasota, FL is $609,325 as of Sep 24, 2026. The likely range is $503,001 to $715,649. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 5239 Winding Way, Sarasota, FL last sell?

5239 Winding Way, Sarasota, FL last sold on May 5, 2025 for $650,000, according to the county's recorded deed. TopHap holds 5 recorded sales for this parcel.

How big is 5239 Winding Way, Sarasota, FL?

5239 Winding Way, Sarasota, FL has 3 bedrooms, 2 bathrooms, 1,512 square feet of living space and a 0.21-acre lot.

When was 5239 Winding Way, Sarasota, FL built?

5239 Winding Way, Sarasota, FL was built in 1958, making it 68 years old. The building has 1 story.

What schools serve 5239 Winding Way, Sarasota, FL?

5239 Winding Way, Sarasota, FL is assigned to Phillippi Shores Elementary School (elementary), rated A+; Brookside Middle School (middle), rated B; Sarasota 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 5239 Winding Way, Sarasota, FL compare to other homes in Sarasota 34242?

Among the 9,770 homes in Sarasota 34242, it is worth more than 25% of them ($609,325 against a typical $879,909), its price per square foot is higher than 3% of them ($403 against a typical $682), it is bigger than 66% of them (1,512 ft² against a typical 1,303 ft²), its lot is bigger than 16% of them (0.21 ac against a typical 0.38 ac) and it is newer than 7% of them (1958 against a typical 1974). Measured against all of Sarasota County, it is worth more than 75% 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 5239 Winding Way, Sarasota, FL?

The 2025 property tax bill for 5239 Winding Way, Sarasota, FL was $7,599. The county assessed it at $662,100.

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