5050 ISLEWORTH COUNTRY CLUB DRIVE
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    +18 more
    Active
    Single Family Residence

    5050 ISLEWORTH COUNTRY CLUB DRIVE

    WINDERMERE, FL, 34786·ISLEWORTH

    MLS# O6438618

    $3,189,000

    4

    Beds

    4.5

    Baths

    3,365

    Sq Ft

    Description

    Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

    Property Overview

    StatusActive
    TypeSingle Family Residence
    Year Built1987
    CityWINDERMERE
    Area34786 - WINDERMERE
    SubdivisionISLEWORTH
    StateFL
    CountyOrange
    List Date09/04/2026
    MLS#O6438618
    List Price$3,189,000

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms4.5
    Full Bathrooms4
    Half Bathrooms1

    Structure

    Garage Capacity2
    ParkingCircular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Golf Cart Parking, Oversized
    Construction MaterialsBlock, Stucco
    RoofConcrete, Tile
    Foundation DetailsBlock
    FlooringTile
    Private PoolYes
    Patio & PorchCovered, Rear Porch

    Size & Lot

    Living Area3,365 sqft
    Lot Size22,514 sqft
    Acres0.52
    Lot DescriptionIn County, Landscaped, On Golf Course, Paved, Private
    Water FrontNo

    Utilities

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

    Additional Features

    Interior FeaturesBuilt-in Features, Central Vaccum, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Window Treatments
    Exterior FeaturesLighting, Rain Gutters, Sprinkler Metered
    AppliancesDishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, 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

    5050 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$28,793 (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
    Maintenance Grounds
    Maintenance
    Private Road
    Security
    Amenities
    Basketball Court
    Cable TV
    Fence Restrictions
    Gated
    Optional Additional Fees
    Playground
    Security
    Vehicle Restrictions

    Community Features

    Association Recreation - Owned
    Clubhouse
    Community Mailbox
    Fitness Center
    Gated Community - Guard
    Golf Carts OK
    Golf
    Irrigation-Reclaimed Water
    Playground
    Pool
    Restaurant
    Special Community Restrictions
    Tennis Court(s)
    Street Lights
    Water Features
    Community Boat Ramp,Lake,Water Access,Waterfront

    Pet Policy

    Pets AllowedBreed Restrictions, Cats OK, Dogs OK, 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 COMPASS FLORIDA LLC · Toni Cafferty

    Frequently Asked Questions

    What is the asking price for 5050 ISLEWORTH COUNTRY CLUB DRIVE?

    The listing price for 5050 ISLEWORTH COUNTRY CLUB DRIVE is $3,189,000.

    How many bedrooms and bathrooms does 5050 ISLEWORTH COUNTRY CLUB DRIVE have?

    This property features 4 bedrooms and 4 full bathrooms plus 1 half bath(s).

    What is the square footage of 5050 ISLEWORTH COUNTRY CLUB DRIVE?

    The living area is approximately 3,365 square feet.

    What community is 5050 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 5050 ISLEWORTH COUNTRY CLUB DRIVE built?

    This property was built in 1987.

    What schools are near 5050 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 5050 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 2026-09-05. 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.