5092 ISLEWORTH COUNTRY CLUB DRIVE
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    +55 more
    Active
    Single Family Residence

    5092 ISLEWORTH COUNTRY CLUB DRIVE

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6446272

    $8,500,000

    4

    Beds

    5

    Baths

    7,100

    Sq Ft

    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 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 Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1995
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date10/01/2026
    MLS#O6446272
    List Price$8,500,000

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms5
    Full Bathrooms5
    Half Bathrooms0

    Structure

    StyleMediterranean
    Garage Capacity4
    ParkingCircular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
    Construction MaterialsBlock, Stucco
    RoofTile
    Foundation DetailsSlab
    FlooringBrick, Carpet, Marble, Travertine, Wood
    Private PoolYes

    Size & Lot

    Living Area7,100 sqft
    Lot Size40,620 sqft
    Acres0.93
    Lot DescriptionLandscaped, On Golf Course, Oversized Lot, Paved, Private
    Water FrontNo

    Utilities

    HeatingCentral, Zoned
    CoolingCentral Air, Zoned
    WaterPublic
    SewerSeptic Tank

    Additional Features

    Interior FeaturesBuilt-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 FeaturesBalcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
    AppliancesBar 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

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About ISLEWORTH

    5092 ISLEWORTH COUNTRY CLUB DRIVE is located in the ISLEWORTH community in WINDERMERE, FL. Part of Orange County.

    The ISLEWORTH neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$57,070.63 (2026)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationDan O’Connell
    HOA Fee$3,672 / quarterly
    Fee Includes
    Guard - 24 Hour
    Cable TV
    Escrow Reserves Fund
    Internet
    Maintenance Grounds
    Maintenance
    Private Road
    Security
    Amenities
    Cable TV
    Gated
    Maintenance
    Optional Additional Fees
    Playground
    Security

    Community Features

    Association Recreation - Owned
    Community Mailbox
    Fitness Center
    Golf Carts OK
    Golf
    Playground
    Pool
    Tennis Court(s)
    Street Lights

    Pet Policy

    Pets AllowedBreed Restrictions, Yes

    Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of ISLEWORTH REALTY LLC · Michelle Corbin

    Frequently Asked Questions

    What is the asking price for 5092 ISLEWORTH COUNTRY CLUB DRIVE?

    The listing price for 5092 ISLEWORTH COUNTRY CLUB DRIVE is $8,500,000.

    How many bedrooms and bathrooms does 5092 ISLEWORTH COUNTRY CLUB DRIVE have?

    This property features 4 bedrooms and 5 full bathrooms.

    What is the square footage of 5092 ISLEWORTH COUNTRY CLUB DRIVE?

    The living area is approximately 7,100 square feet.

    What community is 5092 ISLEWORTH COUNTRY CLUB DRIVE located in?

    This property is located in the ISLEWORTH community in WINDERMERE, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 5092 ISLEWORTH COUNTRY CLUB DRIVE built?

    This property was built in 1995.

    What schools are near 5092 ISLEWORTH COUNTRY CLUB DRIVE?

    WINDERMERE is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 5092 ISLEWORTH COUNTRY CLUB DRIVE?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-10-02. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.