5092isleworthcountryclubdrivewindermerefl34786

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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