




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
Bedrooms & Bathrooms
Structure
Size & Lot
Utilities
Additional Features
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
HOA, Community & Pets
HOA & Recurring Fees
Community Features
Pet Policy
Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.
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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.
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