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Single Family ResidenceResidential
$470,568$497 / 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 Sep 24, 2026
Last sold for $299,000 on Jul 23, 2019

1440 CHESTNUT AVE

WINTER PARK, FL 32789
2
Beds
2
Baths
947 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.
4,285 ft²
Lot SizeThe size of the land the home sits on, from county records.
1970
Year BuiltThe year the home was originally built, according to county records.
1
StoriesHow many floors the home has above ground.
1
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$471K
$432K low$510K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$299,000 · Jul 23, 2019

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,777 (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.$285,093 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$277,058
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$422,020

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.0.10
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Forced Air
CoolingThe type of cooling or air conditioning in the home.Central
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 · 200 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
Lakemont Elementary SchoolB+
Elementary · Grades KG–5 · 0.5 mi
M
Maitland Middle SchoolB
Middle · Grades 6–8 · 1.6 mi
H
Winter Park High SchoolB+
High · Grades 9–12 · 2.1 mi

District: Orange County School District

Neighborhood · ZIP 32789These 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.112
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.134
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.22

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.91%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.38%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.6.1%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.9%
PopulationHow many people live in this area.27,837
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.2,897 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$113,286
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$168,785
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

1440 Chestnut Ave 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 76% of homes in Winter Park 32789
  • Costs more per square foot than 98% of homes in Orange County
  • Smaller than 92% of homes in Orange County
  • Has a smaller lot than 92% of homes in Orange County
  • Older than 81% of homes in Orange County

What homes are worth in Winter Park 32789

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

This home
$190K$5.4M

This home is worth more than 24% of homes in Winter Park 32789.

How it measures up in Winter Park 32789

The dot is this home. The mark in the middle is the typical home in Winter Park 32789.

Estimated value$470,568
CheaperTypical $889,002Pricier

Pricier than 24% of homes nearby

Price per ft²$497
CheaperTypical $468Pricier

Pricier than 55% of homes nearby

Living area947 ft²
SmallerTypical 1,957 ft²Bigger

Bigger than 10% of homes nearby

Lot size4,285 ft²
SmallerTypical 0.24 acBigger

Bigger than 10% of homes nearby

Year built1970
OlderTypical 1967Newer

Newer than 55% of homes nearby

How 1440 Chestnut Ave ranks against every home in each area.
MeasureThis homeWinter Park 32789Orange County
Estimated valuepricier than$470,56824% of homes64% of homes
Price per ft²pricier than$49755% of homes98% of homes
Living areabigger than947 ft²10% of homes8% of homes
Lot sizebigger than4,285 ft²10% of homes8% of homes
Year builtnewer than197055% of homes19% of homes

About 1440 Chestnut Ave

How much is 1440 Chestnut Ave, Winter Park, FL worth?

The TopHap Estimate for 1440 Chestnut Ave, Winter Park, FL is $470,568 as of Sep 24, 2026. The likely range is $431,510 to $509,626. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 1440 Chestnut Ave, Winter Park, FL last sell?

1440 Chestnut Ave, Winter Park, FL last sold on Jul 23, 2019 for $299,000, according to the county's recorded deed. TopHap holds 4 recorded sales for this parcel.

How big is 1440 Chestnut Ave, Winter Park, FL?

1440 Chestnut Ave, Winter Park, FL has 2 bedrooms, 2 bathrooms, 947 square feet of living space and a 0.10-acre lot.

When was 1440 Chestnut Ave, Winter Park, FL built?

1440 Chestnut Ave, Winter Park, FL was built in 1970, making it 56 years old. The building has 1 story.

What schools serve 1440 Chestnut Ave, Winter Park, FL?

1440 Chestnut Ave, Winter Park, FL is assigned to Lakemont Elementary School (elementary), rated B+; Maitland Middle School (middle), rated B; Winter Park 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 1440 Chestnut Ave, Winter Park, FL compare to other homes in Winter Park 32789?

Among the 10,231 homes in Winter Park 32789, it is worth more than 24% of them ($470,568 against a typical $889,002), its price per square foot is higher than 55% of them ($497 against a typical $468), it is bigger than 10% of them (947 ft² against a typical 1,957 ft²), its lot is bigger than 10% of them (4,285 ft² against a typical 0.24 ac) and it is newer than 55% of them (1970 against a typical 1967). Measured against all of Orange County, it is worth more than 64% 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 1440 Chestnut Ave, Winter Park, FL?

The 2024 property tax bill for 1440 Chestnut Ave, Winter Park, FL was $3,777. The county assessed it at $285,093.

More homes on Chestnut Ave

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