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$4,330,000
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Property Description
Motivated Seller - 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 in 2024 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.
Full Property Details
Full Property Details for 9724 Chestnut Ridge Dr
General
- Sold For: $4,330,000
- HOA FEE: $1,043/month
- HOA FEE FREQ.: Quarterly
- Taxes: $38,334 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6310606
- Added to Site: 240 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 10
- Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Wet Bar, Window Treatments
- Appliances: Bar Fridge, Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Carpet, Tile, Travertine, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 6
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Cable TV, Gated, Maintenance, Playground, Security
- Pool: Yes
- Private Pool: Yes
- Pool Description: In Ground, Salt Water
- Spa: Yes
- Spa Description: In Ground
Exterior
- Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
- Deck/Patio: Patio, Rear Porch, Screened
- Porch/Patio/Deck: Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 6
- Covered Spaces: 6
- Parking Features: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: ISLEWORTH
- Driving 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.
- Direction Faces: Northeast
School Information
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, Playground
- Optional Amenities: Cable TV, Gated, Maintenance, Playground, Security
- Association: Yes
- Assoc. Name: Dan O'Connell
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
- Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Zoned
Utilities
- Sewer: Septic Tank
- Water District: LAKE BESSIE
- Water: Canal/Lake For Irrigation, Public
- Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Public, Street Lights, Underground Utilities
Structural Information
- Architectural Info: Custom, Mediterranean
- Architectural Style: Custom, Mediterranean
- Exterior Const.: Block, Stucco
- Roof: Metal
- Stories/Levels: Two
- Square Feet: 5,557
- Sq. Ft. Source: Public Records
- Living Area: 5,557 Sq. Ft.
- Year Built: 1990
Lot Features
- Property View: Pool, Water
- Lot Size (Acres): 0.56
- Lot Size (Sq. Ft.): 24,255
- Lot Size: 24255
- Frontage: Street Paved
- Street/Road Desc.: Paved
- Fencing (Description): Fenced
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Name: LAKE BESSIE
- Water Front Desc.: Lake Front
Financial Considerations
- Association Fee: $3,129
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $38,334.25
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ISLEWORTH 16/118 LOT 15
- Flood Zone Info: AE
- APN: 282316389900150
- Property ID: 282316389900150
Listed by Isleworth Realty Llc
Sold by Isleworth Realty Llc
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Schools
Schools serving 9724 Chestnut Ridge Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 1.7 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 1.1 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 9724 Chestnut Ridge Dr
Date
Details
Price
Change
Source
7/25/2025
Sold
$4,330,000
-9.79%
MLS
5/20/2025
Listed
$4,800,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
9724 Chestnut Ridge Dr, Windermere, FL 34786 (MLS# O6310606) is a Single Family property that was sold at $4,330,000 on July 25, 2025. Want to learn more about 9724 Chestnut Ridge Dr? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

