5092 Isleworth Country Club Drive, Windermere, FL 34786
- 7,100 Sq Ft ($1,197 per sqft)
- 4
- 5
ID: O6446272
For Sale
:
$8,500,000
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.
Equipment:
- 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
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
Exterior Features:
- Balcony
- Lighting
- Outdoor Grill
- Outdoor Shower
- Rain Gutters
View:
- Garden
- Golf Course
- Trees/Woods
- Water
Amenities:
- Cable TV
- Gated
- Maintenance
- Optional Additional Fees
- Playground
- Security
Financial Information:
- Taxes: $57,070.63
- Tax Year: 2026
- Association Fee: $3,672.00
- Association Fee Frequency: Quarterly
Room Dimensions:
- Laundry: Laundry Room
School Information:
- Elementary School: Windermere Elem
- Middle School: Chain Of Lakes Middle
- Junior High: Chain Of Lakes Middle
- High School: Olympia High
Additional Information:
- Building Description: Mediterranean
- MLS Area: 34786 - Windermere
- Total Square Footage: 10,319
- Price per Square Feet: $1,197.18
- Water: Public
- Construction: Block, Stucco
- Date Listed: 2026-10-01 00:00:00
- Pool: Y
- Pool Description: In Ground, Lighting
- Private Spa: Y
- Furnished: Negotiable
- Windows: Drapes, Shutters, Window Treatments
- Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
- Garage Description: Y
- Garage Spaces: 4
- Attached Garage: Y
- Flooring: Brick, Carpet, Marble, Travertine, Wood
- Roof: Tile
- Heating: Central, Zoned
- Cooling: Central Air, Zoned
- Fireplace: Y
- Security: Closed Circuit Camera(S), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(S)
- Laundry: Laundry Room
- 55+ Community: N
- Pets: Breed Restrictions, Yes
- Sewer: Septic Tank
- Lot Desc.: Landscaped, On Golf Course, Oversized Lot, Paved, Private
- Parcel ID: 16-23-28-3899-0
- Amenities: Cable Tv, Gated, Maintenance, Optional Additional Fees, Playground, Security