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.
Sold for $4,330,000
$4,330,000
9724 Chestnut Ridge Dr, Windermere, FL 34786
5beds
5,557sqft
Single Family Residence
Built in 1990
0.56 Acres Lot
$4,252,300 Zestimate®
$779/sqft
$7,790 Estimated rent
Home value
$4,252,300
$3.87M - $4.68M
$7,790/mo
Zestimate® history
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Zillow last checked: 8 hours ago
Listing updated: July 25, 2025 at 08:18am
Listing Provided by:
Carey Sheffield 407-961-2979,
ISLEWORTH REALTY LLC 407-909-9000,
Michelle Corbin 407-491-2690,
ISLEWORTH REALTY LLC
Bought with:
Michelle Corbin, 3418089
ISLEWORTH REALTY LLC
Source: Stellar MLS,MLS#: O6310606
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 6
Primary bedroom
- Description: Room1
- Features: Built-In Shelving, Ceiling Fan(s), Dual Sinks, Garden Bath, Granite Counters, Tub with Separate Shower Stall, Walk-In Closet(s)
- Level: First
- Area: 405 Square Feet
- Dimensions: 15x27
Bedroom 2
- Description: Room2
- Features: Pantry, Built-in Closet
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Bedroom 3
- Description: Room3
- Features: Built-In Shelving, Ceiling Fan(s), Pantry, Shower No Tub, Stone Counters, Built-in Closet
- Level: Second
- Area: 285 Square Feet
- Dimensions: 19x15
Bedroom 4
- Description: Room4
- Features: Built-In Shelving, Pantry, Shower No Tub, Stone Counters, Built-in Closet
- Level: Second
- Area: 168 Square Feet
- Dimensions: 14x12
Bedroom 5
- Description: Room8
- Features: Built-in Closet
- Level: Second
- Area: 276 Square Feet
- Dimensions: 12x23
Family room
- Description: Room6
- Features: Built-In Shelving, Ceiling Fan(s)
- Level: First
- Area: 368 Square Feet
- Dimensions: 16x23
Great room
- Level: First
Kitchen
- Level: First
Media room
- Description: Room5
- Features: Bar, Pantry, Granite Counters, Wet Bar
- Level: Second
- Area: 440 Square Feet
- Dimensions: 20x22
Office
- Description: Room7
- Level: First
Heating
- Central, Zoned
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Gas Water Heater, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Laundry: Inside, Laundry Room
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
- Flooring: Carpet, Tile, Travertine, Hardwood
- Doors: French Doors, Outdoor Grill, Outdoor Kitchen
- Windows: Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 8,162
- Total interior livable area: 5,557 sqft
Property
Parking
- Total spaces: 6
- Parking features: Circular Driveway, Golf Cart Garage, Golf Cart Parking, Ground Level
- Attached garage spaces: 6
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Patio, Rear Porch, Screened
- Exterior features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
- Has private pool: Yes
- Pool features: In Ground, Salt Water
- Has spa: Yes
- Spa features: In Ground
- Fencing: Fenced
- Has view: Yes
- View description: Pool, Water, Lake
- Has water view: Yes
- Water view: Water,Lake
- Waterfront features: Lake Front, Lake Privileges, Lift, Skiing Allowed
- Body of water: LAKE BESSIE
Lot
- Size: 0.56 Acres
- Features: Landscaped, Near Golf Course
- Residential vegetation: Mature Landscaping, Oak Trees
Details
- Parcel number: 282316389900150
- Zoning: P-D
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Custom,Mediterranean
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Block, Slab
- Roof: Metal
Condition
- New construction: No
- Year built: 1990
Utilities & green energy
- Sewer: Septic Tank
- Water: Canal/Lake For Irrigation, Public
- Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Public, Street Lights, Underground Utilities
Community & neighborhood
Community
- Community features: Community Boat Ramp, Water Access, Community Mailbox, Gated Community - Guard, Golf Carts OK, Golf, Playground
Location
- Region: Windermere
- Subdivision: ISLEWORTH
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $1,043 monthly
- Amenities included: Cable TV, Gated, Maintenance, Playground, Security
- Services included: 24-Hour Guard, Cable TV, Reserve Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
- Association name: Dan O'Connell
- Association phone: 407-909-2071
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 7/25/2025 | Sold | $4,330,000-9.8%$779/sqft |
Source:  Stellar MLS #O6310606 Report a problem | ||
| 6/27/2025 | Pending sale | $4,800,000$864/sqft |
Source: Stellar MLS #O6310606 Report a problem | ||
| 5/20/2025 | Listed for sale | $4,800,000+61.3%$864/sqft |
Source: Stellar MLS #O6310606 Report a problem | ||
| 5/10/2019 | Listing removed | $2,975,000$535/sqft |
Source: ISLEWORTH REALTY LLC #O5706286 Report a problem | ||
| 11/9/2018 | Price change | $2,975,000-3.3%$535/sqft |
Source: ISLEWORTH REALTY LLC #O5706286 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $38,334 +7.2% | $2,358,689 +3% |
| 2023 | $35,756 +2.9% | $2,289,989 +3% |
| 2022 | $34,765 +1.1% | $2,223,290 +3% |
Find assessor info on the county website
Neighborhood: 34786
Nearby schools
GreatSchools rating
- 10/10Windermere Elementary SchoolGrades: PK-5Distance: 1.7 mi
- 3/10Chain Of Lakes Middle SchoolGrades: 6-8Distance: 1.2 mi
- 5/10Olympia High SchoolGrades: 9-12Distance: 1.1 mi
Schools provided by the listing agent
- Elementary: Windermere Elem
- Middle: Chain of Lakes Middle
- High: Olympia High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$4,252,300
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$4,252,300
- Florida
- Orange County
- Windermere
- 34786
- 9724 Chestnut Ridge Dr