9724 Chestnut Ridge Dr, Windermere, FL 34786
$4,800,000
Less Photos /\
Home Description
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.
- MLS #: O6310606
- Address: 9724 Chestnut Ridge Dr
- Levels: Two
- City: Windermere
- Zip: 34786
- County: Orange
- Subdivision: Isleworth
- Community Features: Community Mailbox,Gated Community - Guard,Golf,Golf Carts OK,Playground,Street Lights
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Private Pool: True
- Pool Features: In Ground,Salt Water
- Spa Features: In Ground
- Water View: Lake
- Water Name: LAKE BESSIE
- Water Frontage: Lake Front
- Water Feet: 100
- Water Extras: Lift,Skiing Allowed
- Water Access: Lake
- Interior Features: 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
- Appliances: Bar Fridge,Built-In Oven,Cooktop,Dishwasher,Disposal,Dryer,Freezer,Gas Water Heater,Microwave,Range Hood,Refrigerator,Washer,Wine Refrigerator
- Floor Covering: Carpet,Tile,Travertine,Wood
- Bathroom 2 Features: Closet Pantry
- Bathroom 3 Features: Built-In Shelving,Ceiling Fan(s),Closet Pantry,Shower No Tub,Stone Counters
- Media Room Features: Bar,Closet Pantry,Granite Counters,Wet Bar
- Family Room Features: Built-In Shelving,Ceiling Fan(s)
- Architectural Style: Custom,Mediterranean
- Exterior Features: French Doors,Lighting,Outdoor Grill,Outdoor Kitchen,Rain Gutters
- Exterior Contruction: Block,Stucco
- Foundation: Block,Slab
- Front Exposure: Northeast
- Roof: Metal
- Building Sqft: 8162
Available now at $4,800,000
Approximate Room Sizes / Descriptions
| Bathroom 2 | 11x12 | First | Travertine |
| Bathroom 3 | 19x15 | Second | Porcelain Tile |
| Media Room | 20x22 | Second | Carpet |
| Family Room | 16x23 | First | Travertine |
| Office | | First | |
| Kitchen | | First | |
| Great Room | | First | |
| Primary Bedroom | 15x27 | First | Tile |
| Bedroom 4 | 14x12 | Second | Porcelain Tile |
| Bedroom 5 | 12x23 | Second | Porcelain Tile |
- Attached Garage: True
- Garage: True
- Garage Spaces: 6
- Garage Feature: Circular Driveway,Golf Cart Garage,Golf Cart Parking,Ground Level
- Carport: False
- Carport Spaces: 0
- Air Conditioning: Central Air
- Heating: Central,Zoned
- Utilities: BB/HS Internet Available,Cable Connected,Electricity Connected,Fire Hydrant,Natural Gas Connected,Public,Underground Utilities
- Lot Sqft: 24255.00
- Lot Acres: 0.5600
- Total Acre: 1/2 to less than 1
- Lot Num: 15
- HOA Fees: $3,129 Quarterly
- HOA Monthly Amount: $1,043
- HOA/Community Assoc: Required
- Senior Community: False
- Style: Single Family Residence
- Location: Landscaped,Near Golf Course,Paved
- Maintenance Includes: Cable TV,Escrow Reserves Fund,Guard - 24 Hour,Internet,Maintenance,Maintenance Grounds,Private Road,Security
- Pets Allowed: Breed Restrictions
- Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
- : 407-909-9000
Neighborhood
The average asking price of a 5 bedroom Windermere home in this zip code is
$2,522,652 (47.4% less than this home).
This home is priced at $864/sqft,
which is 44.3% less than similar homes
in the 34786 zip code.
Map
Map |
Street
Street |
Birds Eye
Birds Eye
Print Map | Driving Directions
Similar Properties For Sale
Nearby Properties For Sale
Financial
- Approx Payment:$23,350*
- Taxes:$38,334
Area Stats
These statistics are updated daily from the My Florida Regional MLS. For further analysis or
to obtain statistics not shown below please call EasyStreet Realty at
(407) 967-1435 and speak with one of our real estate consultants.
Popular Homes
$492,810
$439,900
148
2.0%
51.4%
80
$529,830
$475,000
561
1.6%
47.1%
88
$877,289
$649,993
19
0.0%
36.8%
67
$435,379
$420,000
103
1.9%
53.4%
67
$1,339,933
$1,042,500
50
0.0%
52.0%
99
$725,240
$719,000
17
0.0%
47.1%
297
$830,957
$686,950
30
0.0%
43.3%
46
$577,757
$490,000
722
0.7%
51.0%
77
$1,034,743
$649,990
13
0.0%
69.2%
82
$483,441
$409,000
275
1.1%
58.5%
88
$438,683
$419,900
78
0.0%
43.6%
98
$521,126
$445,000
2424
1.7%
49.6%
101
$720,012
$542,500
218
1.4%
53.7%
71
$1,021,226
$599,900
97
2.1%
50.5%
79
$562,954
$548,480
135
0.7%
38.5%
79
$1,557,839
$1,095,471
48
0.0%
50.0%
122
$537,122
$489,990
173
1.2%
52.6%
78
$693,562
$500,000
3061
1.8%
50.3%
79
$711,764
$620,000
226
0.4%
51.3%
67
$324,028
$310,490
287
1.4%
53.0%
122
$1,898,844
$1,132,500
104
2.9%
57.7%
164
$644,326
$500,842
68
2.9%
57.4%
248
$520,811
$423,990
389
0.8%
49.9%
97
$583,247
$450,000
109
0.9%
49.5%
81
$862,974
$719,900
607
0.7%
50.1%
84
$1,276,138
$749,000
327
0.3%
52.0%
87
$645,491
$496,700
150
0.7%
49.3%
71
Listing Courtesy of ISLEWORTH REALTY LLC.
For information or to schedule a viewing of this property (MLS# O6310606), call: 407-967-1435
9724 Chestnut Ridge Dr, Windermere FL is a single family home of 5557 sqft and
is currently priced at $4,800,000
.
This single family home has 5 bedrooms.
A comparable home for sale at 5001 Latrobe Dr in Windermere is listed at $3,199,999.
In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures
in Windermere, FL.
Aladar On Lake Butler, Bellaria and Lake Cawood Estates are nearby neighborhoods.
MLS O6310606 has been posted on this site since 5/20/2025 (today).
2025
5/22/2025.