$4,800,000

9724 Chestnut Ridge Dr Windermere, FL 34786

5 beds
6 full
5,557 sqft
0.6 acres
$864 / sqft
House

Property details

About 9724 Chestnut Ridge Dr

Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5,557 square feet of luxurious living space. A new metal roof adds both modern appeal and long-term durability, enhancing the home’s overall value and aesthetic. Grand mahogany French doors welcome you into an expansive formal living room, where large picture windows perfectly frame the breathtaking lake vistas. Adjacent, the elegant formal dining room connects to a gourmet kitchen featuring smooth granite countertops, a center island with a professional-grade range and contemporary hood, stainless steel appliances, and travertine flooring. A cozy breakfast nook and inviting family room—both with stunning lake views—complete the heart of the home. Wine enthusiasts will appreciate the custom wine cellar, adorned with a reclaimed Old World wooden door and capacity for over 500 bottles. This space seamlessly connects to a richly appointed home office and trophy room, each featuring bespoke wooden built-ins. The primary suite offers a tranquil sitting area overlooking the lake, along with a luxurious en-suite bath that includes dual vanities, a garden tub, and a walk-in shower. Upstairs, three additional bedrooms accompany a home theater with soundproof walls, a built-in wet bar, and intricate wood detailing—creating the ultimate cinematic experience. Outdoors, a spacious lanai with a summer kitchen overlooks an elevated terrace, pool, and spa—perfect for entertaining or relaxing while enjoying spectacular sunsets and nightly fireworks from nearby theme parks. This rare lakefront gem blends timeless elegance with a prime location, offering an unparalleled lifestyle in one of Central Florida’s most exclusive communities.

Highlights

Home typeSingle Family Residence
HeatingCentral, Zoned
StatusActive
CoolingCentral Air
Size5,557 sqft
Lot size0.56 Acres
Year built1990
ParkingCircular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
MLS #O6310606
Attached garage6 spaces
WaterfrontLake Front
ViewPool, Water
Private poolYes

Summary

  • Full Bathrooms: 6
  • Appliances: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Cooler
  • Flooring Type: Carpet, Tile, Travertine, Wood
  • Interior: Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
  • Total Bedroom Count: 5
  • Garage Space: 6 spaces
  • Attached Garage: Yes
  • Private Pool: Yes
  • Parking: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
  • Waterfront: Lake Front
  • View: Pool, Water
  • Exterior: French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
  • Architectural Style: Custom, Mediterranean
  • Heating: Central, Zoned
  • Cooling: Central Air
  • List Price: $4,800,000
  • Price/SqFt: $863
  • HOA Amount: $3129 Quarterly
  • Annual Tax Amount: $35,755
  • Tax Year: 2023
  • Lot: Landscaped, Near Golf Course, Paved
  • Directions: I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive.Turn right on Latrobe, turn right on Chestnut Ridge Drive. Estate will be on the Left.
  • Year Built: 1990
  • Living Area: 5,557 SqFt
  • Lot Size: 0.56 Acres
  • MLS Number: O6310606
  • MLS Name: MFRMLS
  • Office Name: ISLEWORTH REALTY LLC
  • Office Phone: (407) 909-9000
  • Listing Agent: Carey Sheffield

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Last updated on: 5/21/2025, 8:19:31 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

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9724 Chestnut Ridge Dr, Windermere, FL 34786 - view of front of home featuring a standing seam roof, stucco siding, and metal roof

$4,800,000

9724 Chestnut Ridge Dr

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Price information

Property sales

DateEventPrice
Jul 31, 1997
Home Sold
$940,000

Tax history

YearAssessmentProperty Tax
2023$2,289,989$35,755
2022$2,223,290$34,764
2021$2,158,534$34,764
2020$2,169,169$34,375
2018$2,097,900$34,618
2017$2,054,750$34,267

History based on county public records data.

Nearby schools

10

Windermere Elementary School

Public District KG-5

1.7 mi

11125 Park Ave

8

Palm Lake Elementary School

Public District KG-5

1.8 mi

8000 Pin Oak Dr

8

Thornebrooke Elementary School

Public District PK-5

2.4 mi

601 Thornebrooke Dr

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $94,580. Most Windermere, FL residents have annual incomes between $35k-100k. Most families are married, no kids. The majority of residents in this area have post secondary degree education.

How much money do the neighbors make?

13%
<35k
40%
35k-100k
23%
100k-200k
24%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

24%
Single, No Kids
6%
Single, with Kids
44%
Married, No Kids
26%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

13%
<11 yrs old
11%
12-17 yrs old
12%
18-34 yrs old
51%
35-64 yrs old
13%
65+ yrs old

What do the neighbors do for fun?

  • Hiking/backpackingHiking/backpacking
  • Skiing/snowboardingSkiing/snowboarding
  • Men's TennisMen's Tennis

Where do the neighbors shop?

  • Nordstrom RackNordstrom Rack
  • NordstromNordstrom
  • BloomingdalesBloomingdales

Where do the neighbors go to eat?

  • ChipotleChipotle
  • California Pizza KitchenCalifornia Pizza Kitchen
  • Bonefish GrillBonefish Grill

What do the neighbors drive?

  • MazdaMazda
  • BMWBMW
  • LexusLexus

What do the neighbors listen to?

  • RockRock
  • Talk/PersonalityTalk/Personality
  • NewsNews
All data provided by Home Junction and Claritas

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Frequently asked questions

About 9724 Chestnut Ridge Dr

The listing price of 9724 Chestnut Ridge Dr property is $4,800,000.

The property 9724 Chestnut Ridge Dr is a house located in Windermere, Florida, 34786.

Active Listing: 9724 Chestnut Ridge Dr is For Sale (Active/New) which means the seller is accepting offers.

The nearby schools for 9724 Chestnut Ridge Dr are: Windermere Elementary School (GreatSchools Rating 10/10), Palm Lake Elementary School (GreatSchools Rating 8/10), Thornebrooke Elementary School (GreatSchools Rating 8/10), Chain of Lakes Middle School (GreatSchools Rating 3/10), Windy Ridge School (GreatSchools Rating 8/10), Southwest Middle School (GreatSchools Rating 7/10), Olympia High School (GreatSchools Rating 6/10), Dr. Phillips High School (GreatSchools Rating 5/10), Universal Education Center (GreatSchools Rating 4/10).

According to the records, the last property tax for 2023 is $35,755 (source: MLS/based on county public records data).

The last sale was on July 31, 1997 for $940,000 (source: MLS/tax record).

The property at 9724 Chestnut Ridge Dr has 5 bedrooms and 6 bathrooms.

The property 9724 Chestnut Ridge Dr is 5,557 SqFt (source: MLS/tax record).

The year of construction for 9724 Chestnut Ridge Dr is 1990.

This home is located at 9724 Chestnut Ridge Dr in Windermere, FL and zip code 34786 in the Lake Butler neighborhood. This 5,557 square foot home, which was built in 1990, sits on a 0.56 acre lot. Features: 5 bedrooms, 6 bathrooms. It has been listed on Rocket Homes since May 20, 2025 and is currently priced at $4,800,000.

While more than 2 listings in Windermere, FL in April 2025 were sold above asking price, there were more than 9 listings sold at asking price, and more than 56 were sold below. The inventory of homes for sale in Windermere, FL between March and April 2025 increased by 11.1%. The median list price of listings available in April 2025 was $752,895, while the average time on the real estate market was 66 days.

From Rocket Homes Real Estate and based on county public records data.

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