5092isleworthcountryclubdrivewindermerefl34786
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4 Beds
5 Full baths
7,100SqFt
Active
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.
Property Details | ||
|---|---|---|
| Price | $8,500,000 | |
| Bedrooms | 4 | |
| Full Baths | 5 | |
| Half Baths | 0 | |
| Property Style | Mediterranean | |
| Lot Size Area | 40620 | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.93 | |
| Property Type | Residential | |
| Sub type | SingleFamilyResidence | |
| MLS Sub type | Single Family Residence | |
| Features | Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Central Vacuum, Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments | |
| Exterior Features | Balcony, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters | |
| Year Built | 1995 | |
| Subdivision | ISLEWORTH | |
| View | Garden, Golf Course, Trees/Woods, Water | |
| Roof | Tile | |
| Waterfront | BUTLER CHAIN OF LAKES | |
| Heating | Central, Zoned | |
| Foundation | Slab | |
| Lot Description | Landscaped, On Golf Course, Oversized Lot | |
| Laundry Features | Laundry Room | |
| Pool features | In Ground, Lighting | |
| Parking Description | Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage | |
| Garage spaces | 4 | |
| Association Name | Dan O’Connell | |
| Association Fee | 3672 | |
| Association Amenities | Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security | |
Geographic Data | ||
| Directions | I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right. | |
| County | Orange | |
| Latitude | 28.488455 | |
| Longitude | -81.519893 | |
| Market Area | 34786 - Windermere | |
Address Information | ||
| Address | 5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786 | |
| Postal Code | 34786 | |
| City | WINDERMERE | |
| State | FL | |
| Country | United States | |
Listing Information | ||
| Listing Office | ISLEWORTH REALTY LLC | |
| Listing Agent | Michelle Corbin | |
| Special listing conditions | None | |
| Ownership | Fee Simple | |
| Terms | Cash, Conventional | |
| Virtual Tour URL | https://player.vimeo.com/video/1230185615?h=e9768a3a03&badge=0&autopause=0&player_id=0&app_id=58479 | |
School Information | ||
| Elementary School | Windermere Elem | |
| Middle School | Chain of Lakes Middle | |
| High School | Olympia High | |
MLS Information | ||
| Days on market | 0 | |
| MLS Status | Active | |
| Listing Date | Oct 1, 2026 | |
| Listing Last Modified | Oct 1, 2026 | |
| Tax ID | 162328389900480 | |
| Tax Year | 2026 | |
| Tax Annual Amount | 57070 | |
| MLS Area | 34786 - Windermere | |
| MLS # | O6446272 | |
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