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Single Family ResidenceResidential
$3,236,810$650 / 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 90How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Jul 14, 2026
Last sold for $3,250,000 on Sep 26, 2025

9743 CHESTNUT RIDGE DR

WINDERMERE, FL 34786
5
Beds
6
Baths
4,979 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.
1.15 ac
Lot SizeThe size of the land the home sits on, from county records.
1987
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
4
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$3.2M
$2.9M low$3.6M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$3,250,000 · Sep 26, 2025
Est. Owner EquityRoughly how much of the home's value the owner would keep after paying off known loans. It is our estimate minus the loans still owed.$836,810
Est. Lendable EquityThe part of the owner's equity a lender would typically let them borrow against — about 80% of their equity.$669,448
Loan-to-ValueHow much is still owed on the home compared to what it is worth. 80% means loans equal 80% of our estimate, so it shifts when the estimate does.74%
1st MortgageA loan still believed to be open on this home, in the order lenders get repaid. The first position is paid back before the second.$2,400,000
WINTER PARK NATIONAL BANK · recorded Sep 26, 2025

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$22,676 (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.$1,444,886 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$1,404,165
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$2,151,620

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
CountyOrange
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.2000
Lot (acres)The size of the land the home sits on, from county records.1.15
RoofThe main material covering the roof, such as asphalt shingle or tile.Tile
HeatingThe type of heating system in the home.Forced Air
CoolingThe type of cooling or air conditioning in the home.Central
FireplaceWhether the home has a fireplace, and what kind.Yes
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.Porch · 1,250 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.

M
Chain of Lakes Middle SchoolD+
Middle · Grades 6–8 · 1.1 mi
H
Olympia High SchoolC
High · Grades 9–12 · 1.1 mi
E
Windermere Elementary SchoolA+
Elementary · Grades KG–5 · 1.6 mi

District: Orange County School District

Neighborhood · ZIP 34786These 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.73
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.174
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.26

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.41%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.5.3%
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.50,564
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.1,760 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$129,836
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$181,426
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%

Ownership

OccupancyWhether the owner appears to live here or somewhere else. It is inferred from the mailing address on record.Owner occupied
Company ownedWhether the owner is a company or trust rather than a person.No

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

9743 Chestnut Ridge 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.

  • Among the most valuable homes in Orange County
  • Among the highest price per square foot in Orange County
  • Bigger than 98% of homes in Orange County
  • Has a bigger lot than 95% of homes in Orange County
  • Older than 93% of homes in Isleworth

What homes are worth in Windermere 34786

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

This home
$318K$4.4M

This home is worth more than 96% of homes in Windermere 34786.

How it measures up in Windermere 34786

The dot is this home. The mark in the middle is the typical home in Windermere 34786.

Estimated value$3,236,810
CheaperTypical $733,490Pricier

Pricier than 96% of homes nearby

Price per ft²$650
CheaperTypical $272Pricier

Pricier than 96% of homes nearby

Living area4,979 ft²
SmallerTypical 2,709 ft²Bigger

Bigger than 90% of homes nearby

Lot size1.15 ac
SmallerTypical 0.25 acBigger

Bigger than 92% of homes nearby

Year built1987
OlderTypical 2006Newer

Newer than 9% of homes nearby

How 9743 Chestnut Ridge Dr ranks against every home in each area.
MeasureThis homeIsleworthWindermere 34786Orange County
Estimated valuepricier than$3,236,81036% of homes96% of homesalmost all homes
Price per ft²pricier than$65044% of homes96% of homesalmost all homes
Living areabigger than4,979 ft²33% of homes90% of homes98% of homes
Lot sizebigger than1.15 ac88% of homes92% of homes95% of homes
Year builtnewer than19877% of homes9% of homes40% of homes

About 9743 Chestnut Ridge Dr

How much is 9743 Chestnut Ridge Dr, Windermere, FL worth?

The TopHap Estimate for 9743 Chestnut Ridge Dr, Windermere, FL is $3,236,810 as of Jul 14, 2026. The likely range is $2,906,911 to $3,566,709. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 9743 Chestnut Ridge Dr, Windermere, FL last sell?

9743 Chestnut Ridge Dr, Windermere, FL last sold on Sep 26, 2025 for $3,250,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.

How big is 9743 Chestnut Ridge Dr, Windermere, FL?

9743 Chestnut Ridge Dr, Windermere, FL has 5 bedrooms, 6 bathrooms, 4,979 square feet of living space and a 1.15-acre lot.

When was 9743 Chestnut Ridge Dr, Windermere, FL built?

9743 Chestnut Ridge Dr, Windermere, FL was built in 1987, making it 39 years old. The building has 2 stories.

What schools serve 9743 Chestnut Ridge Dr, Windermere, FL?

9743 Chestnut Ridge Dr, Windermere, FL is assigned to Chain of Lakes Middle School (middle), rated D+; Olympia High School (high), rated C; Windermere Elementary School (elementary), rated A+. All sit in Orange County School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 9743 Chestnut Ridge Dr, Windermere, FL compare to other homes in Windermere 34786?

Among the 14,934 homes in Windermere 34786, it is worth more than 96% of them ($3,236,810 against a typical $733,490), its price per square foot is higher than 96% of them ($650 against a typical $272), it is bigger than 90% of them (4,979 ft² against a typical 2,709 ft²), its lot is bigger than 92% of them (1.15 ac against a typical 0.25 ac) and it is newer than 9% of them (1987 against a typical 2006). 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 9743 Chestnut Ridge Dr, Windermere, FL?

The 2024 property tax bill for 9743 Chestnut Ridge Dr, Windermere, FL was $22,676. The county assessed it at $1,444,886.

Closest homes

More homes in Windermere 34786

Assigned schools

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