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Single Family ResidenceResidential
$501,300$288 / 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 96How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Oct 21, 2026
Last sold for $2,379 on Nov 11, 2020

5959 PAINTED LEAF DR

WINTER GARDEN, FL 34787
3
Beds
2.5
Baths
1,743 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.
0.11 ac
Lot SizeThe size of the land the home sits on, from county records.
2020
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.

Valuation

$501K
$480K low$523K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$2,379 · Nov 11, 2020

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$4,693 (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.$301,232 (2026)
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$435,050

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyORANGE
Lot (acres)The size of the land the home sits on, from county records.0.11
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Forced Air With Air Conditioning
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.No
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Porch · 144 ft²

Transaction History(2)

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.

M
Hamlin Middle SchoolA
Middle · Grades 6–8 · 1.0 mi
E
Hamlin Elementary SchoolA+
Elementary · Grades KG–5 · 1.1 mi
H
Horizon High SchoolB+
High · Grades 9–12 · 4.1 mi

District: Orange County School District

Neighborhood · ZIP 34787These 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.65
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.179
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.20

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.94%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.31%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.6.6%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.1%
PopulationHow many people live in this area.89,446
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.999 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$109,624
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$131,719
Average tempThe average temperature here across a full year.72°F
Annual precipHow much rain and melted snow falls here in a typical year.51 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.64%

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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

5959 Painted Leaf 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 69% of homes in Orange County
  • Costs more per square foot than 84% of homes in Orange County
  • Smaller than 74% of homes in Winter Garden 34787
  • Has a smaller lot than 90% of homes in Orange County
  • Newer than 96% of homes in Orange County

What homes are worth in Winter Garden 34787

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

This home
$201K$1.4M

This home is worth more than 38% of homes in Winter Garden 34787.

How it measures up in Winter Garden 34787

The dot is this home. The mark in the middle is the typical home in Winter Garden 34787.

Estimated value$501,300
CheaperTypical $561,060Pricier

Pricier than 38% of homes nearby

Price per ft²$288
CheaperTypical $242Pricier

Pricier than 83% of homes nearby

Living area1,743 ft²
SmallerTypical 2,267 ft²Bigger

Bigger than 26% of homes nearby

Lot size0.11 ac
SmallerTypical 0.19 acBigger

Bigger than 16% of homes nearby

Year built2020
OlderTypical 2015Newer

Newer than 83% of homes nearby

How 5959 Painted Leaf Dr ranks against every home in each area.
MeasureThis homeWinter Garden 34787Orange County
Estimated valuepricier than$501,30038% of homes69% of homes
Price per ft²pricier than$28883% of homes84% of homes
Living areabigger than1,743 ft²26% of homes52% of homes
Lot sizebigger than0.11 ac16% of homes10% of homes
Year builtnewer than202083% of homes96% of homes

About 5959 Painted Leaf Dr

How much is 5959 Painted Leaf Dr, Winter Garden, FL worth?

The TopHap Estimate for 5959 Painted Leaf Dr, Winter Garden, FL is $501,300 as of Oct 21, 2026. The likely range is $479,748 to $522,852. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 5959 Painted Leaf Dr, Winter Garden, FL last sell?

5959 Painted Leaf Dr, Winter Garden, FL last sold on Nov 11, 2020 for $2,379, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 5959 Painted Leaf Dr, Winter Garden, FL?

5959 Painted Leaf Dr, Winter Garden, FL has 3 bedrooms, 2.5 bathrooms, 1,743 square feet of living space and a 0.11-acre lot.

When was 5959 Painted Leaf Dr, Winter Garden, FL built?

5959 Painted Leaf Dr, Winter Garden, FL was built in 2020, making it 6 years old. The building has 2 stories.

What schools serve 5959 Painted Leaf Dr, Winter Garden, FL?

5959 Painted Leaf Dr, Winter Garden, FL is assigned to Hamlin Middle School (middle), rated A; Hamlin Elementary School (elementary), rated A+; Horizon High School (high), rated B+. All sit in Orange County School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 5959 Painted Leaf Dr, Winter Garden, FL compare to other homes in Winter Garden 34787?

Among the 34,930 homes in Winter Garden 34787, it is worth more than 38% of them ($501,300 against a typical $561,060), its price per square foot is higher than 83% of them ($288 against a typical $242), it is bigger than 26% of them (1,743 ft² against a typical 2,267 ft²), its lot is bigger than 16% of them (0.11 ac against a typical 0.19 ac) and it is newer than 83% of them (2020 against a typical 2015). Measured against all of Orange County, it is worth more than 69% 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 5959 Painted Leaf Dr, Winter Garden, FL?

The 2025 property tax bill for 5959 Painted Leaf Dr, Winter Garden, FL was $4,693. The county assessed it at $301,232.

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