5373 ISLEWORTH COUNTRY CLUB DRIVE
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    +55 more
    Active
    Single Family Residence

    5373 ISLEWORTH COUNTRY CLUB DRIVE

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6439156

    $7,200,000

    5

    Beds

    5.5

    Baths

    5,993

    Sq Ft

    Description

    Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.

    Property Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1988
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date09/08/2026
    MLS#O6439156
    List Price$7,200,000

    Bedrooms & Bathrooms

    Bedrooms5
    Bathrooms5.5
    Full Bathrooms5
    Half Bathrooms1

    Structure

    StyleContemporary
    Garage Capacity3
    ParkingCircular Driveway, Garage Door Opener, Garage Faces Side, Parking Pad
    Construction MaterialsBlock, Concrete, Stucco
    RoofTile
    Foundation DetailsBlock, Slab
    FlooringHardwood, Marble, Tile
    Private PoolYes
    BuilderWaters Custom Homes
    Patio & PorchDeck, Front Porch, Rear Porch

    Size & Lot

    Living Area5,993 sqft
    Lot Size22,762 sqft
    Acres0.52
    Lot DescriptionIn County, On Golf Course, Paved, Private
    Water FrontNo

    Utilities

    HeatingCentral, Electric, Zoned
    CoolingCentral Air, Zoned
    WaterPublic
    SewerSeptic Tank

    Additional Features

    Interior FeaturesBuilt-in Features, Cathedral Ceiling(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Tray Ceiling(s)
    Exterior FeaturesOutdoor Kitchen, Rain Gutters
    AppliancesConvection Oven, Cooktop, Dishwasher, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer

    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

    5373 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$43,509 (2025)

    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 Structure
    Maintenance Grounds
    Maintenance
    Security
    Amenities
    Cable TV
    Gated
    Optional Additional Fees
    Playground
    Security
    Secondary HOA
    AssociationIsleworth Community Association

    Community Features

    Buyer Approval Required
    Community Mailbox
    Gated Community - Guard
    Golf Carts OK
    Golf
    Park
    Playground
    Water Features
    Community Boat Ramp,Lake,Private Boat Ramp,Water Access

    Pet Policy

    Pets AllowedBreed Restrictions

    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 STOCKWORTH REALTY GROUP · Rob Rahter

    Frequently Asked Questions

    What is the asking price for 5373 ISLEWORTH COUNTRY CLUB DRIVE?

    The listing price for 5373 ISLEWORTH COUNTRY CLUB DRIVE is $7,200,000.

    How many bedrooms and bathrooms does 5373 ISLEWORTH COUNTRY CLUB DRIVE have?

    This property features 5 bedrooms and 5 full bathrooms plus 1 half bath(s).

    What is the square footage of 5373 ISLEWORTH COUNTRY CLUB DRIVE?

    The living area is approximately 5,993 square feet.

    What community is 5373 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 5373 ISLEWORTH COUNTRY CLUB DRIVE built?

    This property was built in 1988.

    What schools are near 5373 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 5373 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 2026-09-09. 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.