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Single Family ResidenceResidential
$587,857$316 / 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 92How 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 $535,000 on Sep 18, 2026

1808 WESTERN TRAILWAY DR

WINTER GARDEN, FL 34787
3
Beds
2
Baths
1,860 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.
0.14 ac
Lot SizeThe size of the land the home sits on, from county records.
2019
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.

Valuation

$588K
$540K low$636K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$535,000 · Sep 18, 2026

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,389 (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.$458,000 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$150,000
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$308,000
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$458,000

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.0.14
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 · 150 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
Tildenville Elementary SchoolA-
Elementary · Grades PK–5 · 2.4 mi
M
Lakeview Middle SchoolC
Middle · Grades 6–8 · 2.7 mi
H
West Orange High SchoolB+
High · Grades 9–12 · 4.9 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

1808 Western Trailway 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 78% of homes in Orange County
  • Costs more per square foot than 90% of homes in Winter Garden 34787
  • Smaller than 68% of homes in Winter Garden 34787
  • Has a smaller lot than 81% of homes in Orange County
  • Newer than 94% 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
$202K$1.5M

This home is worth more than 55% 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$587,857
CheaperTypical $563,479Pricier

Pricier than 55% of homes nearby

Price per ft²$316
CheaperTypical $242Pricier

Pricier than 90% of homes nearby

Living area1,860 ft²
SmallerTypical 2,250 ft²Bigger

Bigger than 32% of homes nearby

Lot size0.14 ac
SmallerTypical 0.18 acBigger

Bigger than 24% of homes nearby

Year built2019
OlderTypical 2015Newer

Newer than 77% of homes nearby

How 1808 Western Trailway Dr ranks against every home in each area.
MeasureThis homeWinter Garden 34787Orange County
Estimated valuepricier than$587,85755% of homes78% of homes
Price per ft²pricier than$31690% of homes89% of homes
Living areabigger than1,860 ft²32% of homes58% of homes
Lot sizebigger than0.14 ac24% of homes19% of homes
Year builtnewer than201977% of homes94% of homes

About 1808 Western Trailway Dr

How much is 1808 Western Trailway Dr, Winter Garden, FL worth?

The TopHap Estimate for 1808 Western Trailway Dr, Winter Garden, FL is $587,857 as of Oct 21, 2026. The likely range is $539,773 to $635,941. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 1808 Western Trailway Dr, Winter Garden, FL last sell?

1808 Western Trailway Dr, Winter Garden, FL last sold on Sep 18, 2026 for $535,000, according to the county's recorded deed. TopHap holds 4 recorded sales for this parcel.

How big is 1808 Western Trailway Dr, Winter Garden, FL?

1808 Western Trailway Dr, Winter Garden, FL has 3 bedrooms, 2 bathrooms, 1,860 square feet of living space and a 0.14-acre lot.

When was 1808 Western Trailway Dr, Winter Garden, FL built?

1808 Western Trailway Dr, Winter Garden, FL was built in 2019, making it 7 years old. The building has 1 story.

What schools serve 1808 Western Trailway Dr, Winter Garden, FL?

1808 Western Trailway Dr, Winter Garden, FL is assigned to Tildenville Elementary School (elementary), rated A-; Lakeview Middle School (middle), rated C; West Orange 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 1808 Western Trailway Dr, Winter Garden, FL compare to other homes in Winter Garden 34787?

Among the 34,931 homes in Winter Garden 34787, it is worth more than 55% of them ($587,857 against a typical $563,479), its price per square foot is higher than 90% of them ($316 against a typical $242), it is bigger than 32% of them (1,860 ft² against a typical 2,250 ft²), its lot is bigger than 24% of them (0.14 ac against a typical 0.18 ac) and it is newer than 77% of them (2019 against a typical 2015). Measured against all of Orange County, it is worth more than 78% 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 1808 Western Trailway Dr, Winter Garden, FL?

The 2025 property tax bill for 1808 Western Trailway Dr, Winter Garden, FL was $8,389. The county assessed it at $458,000.

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