5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

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$8,500,000

  • 4 BedroomBedrooms
  • 5 BathroomBathrooms
  • 7,100 Sq.Ft.
  • Single Family
  • Active
  • MLS# O6446272
  • Floor Plan
  • Sold on 
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Property Description

Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworths 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.

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Property Details 5092 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6446272
  • Status: Active
  • Date Listed: 10/01/2026
  • Type: Single Family
  • Sub Type: Single Family Residence
  • Year Built: 1995
  • Style: Mediterranean
  • Price: $8,500,000
  • Acres: 0.93
  • Area: 34786 - Windermere
  • County: Orange
  • Subdivision: ISLEWORTH
  • Bedrooms: 4
  • Bathrooms: 5
  • Full Baths: 5
  • Total SqFt: 7,100

Amenities

  • Amenities: Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
  • Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
  • # of Garages: 4
  • Features: Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
  • Waterfront: Yes
  • Waterfront Type: Public
  • Pool: Yes
  • Pool Type: In Ground, Lighting

Interior

  • Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-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
  • Flooring: Brick, Carpet, Marble, Travertine, Wood
  • Appliances: Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Wine Refrigerator
  • Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
  • Heating: Central, Zoned
  • Cooling: Central Air, Zoned

Exterior

  • Exterior Features: Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
  • Lot Description: Landscaped, On Golf Course, Oversized Lot, Paved, Private
  • Roof: Tile
  • Construction: Block, Stucco

Schools

  • Elementary: Windermere Elem
  • Middle: Chain of Lakes Middle
  • High: Olympia High

Additional Information

  • Zoning: P-D

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