9725 CHESTNUT RIDGE DRIVE
Windermere, FL 34786
$5,975,000
Virtually Staged. Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence.
Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed.
The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes.
Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility.
Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings.
Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance.
It is a residence restored with intention, where discretion, craftsmanship, and comfort converge.
Some photos have been virtually staged.
Private showings are easily accommodated, ...
Listing Courtesy of: DOUGLAS ELLIMAN
305-695-6070
| Listing Id: | O6370294 |
|---|---|
| List Price: | $5,975,000 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Active |
| Bedrooms Total: | 7 |
| Bathrooms Full: | 5 |
| Bathrooms Half: | 2 |
| Living Area: | 8,000 |
| Tax Annual Amount: | $29,046 |
| Lot Size Square Feet: | 24,349 |
| Lot Size Acres: | 0.56 |
| Waterfront?: | Yes |
| City: | Windermere |
| County Or Parish: | Orange |
| Subdivision Name: | Isleworth |
| Postal Code: | 34786 |
| Year Built: | 1999 |
| Appliances: | Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer |
| Association Amenities: | Clubhouse, Elevators, Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Storage, Tennis Court(s) |
| Association Fee: | $3,129 |
| Association Fee Frequency: | Quarterly |
| Association Fee Includes: | Guard - 24 Hour, Pool, Maintenance Grounds, Management, Security |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 7 |
| Building Area Source: | Builder |
| Building Area Total: | 11952 |
| Building Area Units: | Square Feet |
| Direction Faces: | West |
| Foundation Details: | Slab |
| Construction Materials: | Block, Stucco |
| Cooling: | Central Air, Zoned |
| Fireplace Features: | Gas, Living Room, Primary Bedroom |
| Directions: | I-4 to Conroy Windermere Road west to Isleworth Golf and Country Club which will be on the left, turn right onto Latrobe Drive and next right onto Chestnut Ridge Drive, the home will be situated on the right. |
| Elementary School: | Windermere Elem |
| Exterior Features: | Fire Pit, Outdoor Kitchen |
| Flooring: | Tile, Travertine, Wood |
| Garage Spaces: | 3 |
| Garage?: | Yes |
| Community Features: | Buyer Approval Required, Clubhouse, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, No Truck/RV/Motorcycle Parking, Playground, Pool, Racquetball, Restaurant, Tennis Court(s) |
| Heating: | Central |
| High School: | Olympia High |
| Interior Features: | Built-in Features, Ceiling Fans(s), Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar |
| Laundry Features: | Laundry Room |
| Levels: | Three Or More |
| Ownership: | Fee Simple |
| Living Area Source: | Builder |
| Living Area Units: | Square Feet |
| Lot Features: | Landscaped, Near Golf Course, Paved |
| Lot Size Acres: | 0.56 |
| Postal Code Plus4: | 8945 |
| Middle Or Junior School: | Chain of Lakes Middle |
| MLS Area Major: | 34786 - Windermere |
| MLS Area Major: | 34786 - Windermere |
| Original List Price: | $6,950,000 |
| Other Equipment: | Fire Pit |
| Parcel Number: | 16-23-28-3899-00-060 |
| Parking Features: | Driveway, Garage Faces Side |
| Patio And Porch Features: | Covered, Enclosed, Rear Porch, Screened |
| Pets Allowed: | Yes |
| Pool Features: | Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile |
| Stories Total: | 2 |
| Township: | 23 |
| Road Surface Type: | Asphalt |
| Roof: | Tile |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2024 |
| Security Features: | Gated Community, Smoke Detector(s) |
| Sewer: | Septic Tank |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Utilities: | Electricity Connected, Water Connected |
| View: | Garden, Pool, Water |
| Water Source: | Public |
| Public Survey Range: | 28 |
| Public Survey Section: | 16 |
| Zoning: | P-D |
| Spa Features: | Heated, In Ground |
| Spa?: | Yes |
| Vegetation: | Mature Landscaping, Trees/Landscaped |
| Waterfront Features: | Pond |
| Window Features: | Skylight(s), ENERGY STAR Qualified Windows |
| Additional Lease Restrictions: | Per Isleworth Community Association |
| Additional Rooms: | Den/Library/Office, Family Room, Formal Living Room Separate, Interior In-Law Suite w/Private Entry, Media Room |
| Alternate Key Folio Num: | 282316389900060 |
| Amenities Additional Fees: | Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club. |
| Approval Process: | Per Isleworth Community Association |
| Association Approval Required Yn: | Yes |
| Association Email: | dan.oconnell@Isleworth.com |
| Association Fee Requirement: | Required |
| Available For Lease Yn: | Yes |
| Building Area Total Srch Sq M: | 1110.38 |
| Calculated List Price By Calcula: | 746.88 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6370294?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6370294?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2009-09-25 |
| Flood Zone Panel: | 12095C0385F |
| Green Verification Count: | 0 |
| Homestead Yn: | No |
| Lease Restrictions Yn: | Yes |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 743.22 |
| Lot Size Square Meters: | 2262 |
| Minimum Lease: | 8-12 Months |
| Monthly Hoa Amount: | $1,043 |
| Pet Restrictions: | Please call the association |
| Room Count: | 5 |
| Sdeo yn: | No |
| Total Acreage: | 1/2 to less than 1 |
| Total Annual Fees: | $12,516 |
| Total Monthly Fees: | $1,043 |
| Unit Number Yn: | No |
| Water Access: | Lake - Chain of Lakes, Pond |
| Water Access Yn: | Yes |
| Water Extras Yn: | No |
| Water Frontage Feet Pond: | 113 |
| Waterfront Feet Total: | 113 |
| Water View: | Yes |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Association Name: | Dan O'Connell |
| Association Phone: | 407-909-2071 |
| Association 2 Yn: | 0 |
| Attribution Contact: | 305-695-6070 |
| Originating System Name : | Stellar MLS |
| Community Association Water Features: | Private Boat Ramp, Water Access, Waterfront |
| Dock Description: | Clubhouse |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-01-02 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
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Property Last Updated: October 21, 2026 08:54 AM - ET
