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Single Family ResidenceResidential
$4,185,355$469 / 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 84How 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 $4,100,000 on Apr 23, 2025

1691 CHESTNUT AVE

WINTER PARK, FL 32789
12
Beds
9 / 2
Baths
8,920 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.
0.42 ac
Lot SizeThe size of the land the home sits on, from county records.
2024
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.

Valuation

$4.2M
$3.5M low$4.9M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$4,100,000 · Apr 23, 2025

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$32,426 (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.$2,086,775 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$400,000
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$1,686,775
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$2,086,775

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.0.42
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
FireplaceWhether the home has a fireplace, and what kind.Yes
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 · 104 ft²

Transaction History(3)

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

1691 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.

  • Among the most valuable homes in Orange County
  • Costs more per square foot than 97% of homes in Orange County
  • Among the largest homes in Orange County
  • Has a bigger lot than 85% of homes in Orange County
  • Among the newest homes in Winter Park 32789

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
$169K$5.1M

This home is worth more than 96% 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$4,185,355
CheaperTypical $865,642Pricier

Pricier than 96% of homes nearby

Price per ft²$469
CheaperTypical $463Pricier

Pricier than 51% of homes nearby

Living area8,920 ft²
SmallerTypical 1,957 ft²Bigger

Bigger than almost all homes nearby

Lot size0.42 ac
SmallerTypical 0.24 acBigger

Bigger than 83% of homes nearby

Year built2024
OlderTypical 1966Newer

Newer than almost all homes nearby

How 1691 Chestnut Ave ranks against every home in each area.
MeasureThis homeWinter Park 32789Orange County
Estimated valuepricier than$4,185,35596% of homesalmost all homes
Price per ft²pricier than$46951% of homes97% of homes
Living areabigger than8,920 ft²almost all homesalmost all homes
Lot sizebigger than0.42 ac83% of homes85% of homes
Year builtnewer than2024almost all homesalmost all homes

About 1691 Chestnut Ave

How much is 1691 Chestnut Ave, Winter Park, FL worth?

The TopHap Estimate for 1691 Chestnut Ave, Winter Park, FL is $4,185,355 as of Oct 21, 2026. The likely range is $3,503,728 to $4,866,982. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 1691 Chestnut Ave, Winter Park, FL last sell?

1691 Chestnut Ave, Winter Park, FL last sold on Apr 23, 2025 for $4,100,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 1691 Chestnut Ave, Winter Park, FL?

1691 Chestnut Ave, Winter Park, FL has 12 bedrooms, 9 bathrooms, 8,920 square feet of living space and a 0.42-acre lot.

When was 1691 Chestnut Ave, Winter Park, FL built?

1691 Chestnut Ave, Winter Park, FL was built in 2024, making it 2 years old. The building has 2 stories.

What schools serve 1691 Chestnut Ave, Winter Park, FL?

1691 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 1691 Chestnut Ave, Winter Park, FL compare to other homes in Winter Park 32789?

Among the 10,239 homes in Winter Park 32789, it is worth more than 96% of them ($4,185,355 against a typical $865,642), its price per square foot is higher than 51% of them ($469 against a typical $463), it is bigger than almost all of them (8,920 ft² against a typical 1,957 ft²), its lot is bigger than 83% of them (0.42 ac against a typical 0.24 ac) and it is newer than almost all of them (2024 against a typical 1966). Measured against all of Orange County, it is worth more than almost all 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 1691 Chestnut Ave, Winter Park, FL?

The 2025 property tax bill for 1691 Chestnut Ave, Winter Park, FL was $32,426. The county assessed it at $2,086,775.

More homes on Chestnut Ave

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