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Single Family ResidenceResidential
$6,000,000$922 / 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 93How 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 $3,100,000 on Dec 9, 2024

9725 CHESTNUT RIDGE DR

WINDERMERE, FL 34786
5
Beds
6.5
Baths
6,509 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.
0.59 ac
Lot SizeThe size of the land the home sits on, from county records.
1999
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

$6M
$5.6M low$6.4M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$3,100,000 · Dec 9, 2024

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$42,817 (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.$2,555,390 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$725,000
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$1,830,390
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$2,555,390

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.0.59
RoofThe main material covering the roof, such as asphalt shingle or tile.Concrete
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.Yes
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.ElevatorPatio · 75 ft²Porch · 3,630 ft²

Transaction History(1)

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 · 1.0 mi
H
Olympia High SchoolC
High · Grades 9–12 · 1.1 mi
E
Windermere Elementary SchoolA+
Elementary · Grades KG–5 · 1.7 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%

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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

9725 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
  • Among the largest homes in Orange County
  • Has a bigger lot than 92% of homes in Orange County
  • Older than 81% of homes in Windermere 34786

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
$334K$4.7M

This home is worth more than almost all 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$6,000,000
CheaperTypical $791,700Pricier

Pricier than almost all homes nearby

Price per ft²$922
CheaperTypical $284Pricier

Pricier than almost all homes nearby

Living area6,509 ft²
SmallerTypical 2,704 ft²Bigger

Bigger than 97% of homes nearby

Lot size0.59 ac
SmallerTypical 0.25 acBigger

Bigger than 79% of homes nearby

Year built1999
OlderTypical 2006Newer

Newer than 19% of homes nearby

How 9725 Chestnut Ridge Dr ranks against every home in each area.
MeasureThis homeIsleworthWindermere 34786Orange County
Estimated valuepricier than$6,000,00089% of homesalmost all homesalmost all homes
Price per ft²pricier than$92294% of homesalmost all homesalmost all homes
Living areabigger than6,509 ft²60% of homes97% of homesalmost all homes
Lot sizebigger than0.59 ac52% of homes79% of homes92% of homes
Year builtnewer than199965% of homes19% of homes61% of homes

About 9725 Chestnut Ridge Dr

How much is 9725 Chestnut Ridge Dr, Windermere, FL worth?

The TopHap Estimate for 9725 Chestnut Ridge Dr, Windermere, FL is $6,000,000 as of Jul 14, 2026. The likely range is $5,550,605 to $6,449,395. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 9725 Chestnut Ridge Dr, Windermere, FL last sell?

9725 Chestnut Ridge Dr, Windermere, FL last sold on Dec 9, 2024 for $3,100,000, according to the county's recorded deed.

How big is 9725 Chestnut Ridge Dr, Windermere, FL?

9725 Chestnut Ridge Dr, Windermere, FL has 5 bedrooms, 6.5 bathrooms, 6,509 square feet of living space and a 0.59-acre lot.

When was 9725 Chestnut Ridge Dr, Windermere, FL built?

9725 Chestnut Ridge Dr, Windermere, FL was built in 1999, making it 27 years old. The building has 2 stories.

What schools serve 9725 Chestnut Ridge Dr, Windermere, FL?

9725 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 9725 Chestnut Ridge Dr, Windermere, FL compare to other homes in Windermere 34786?

Among the 14,935 homes in Windermere 34786, it is worth more than almost all of them ($6,000,000 against a typical $791,700), its price per square foot is higher than almost all of them ($922 against a typical $284), it is bigger than 97% of them (6,509 ft² against a typical 2,704 ft²), its lot is bigger than 79% of them (0.59 ac against a typical 0.25 ac) and it is newer than 19% of them (1999 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 9725 Chestnut Ridge Dr, Windermere, FL?

The 2025 property tax bill for 9725 Chestnut Ridge Dr, Windermere, FL was $42,817. The county assessed it at $2,555,390.

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