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Property for sale at 5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786
Property for sale at 5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786
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5050 Isleworth Country Club DriveWindermere, FL, 34786

4beds
5baths
3,365sqft
Single Family Residence
Built in 1987
$3,672 Quarterly HOA Fee
$3,189,000
For sale
Price per sqft
$948
Days on market
34
Listed Sep 4, 2026
MLS #O6438618Updated Sep 5, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
5050 Isleworth Country Club Drive
City
Windermere
State
FL
ZIP code
34786
Year built
1987
New construction
No
Attached property
No
Faces
Southeast
Rooms
13
Living area
3,365 sqft
Total building area
4,843 sqft
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

EventPrice
Listed for saleMLS #O6438618$3,189,000
History may be incomplete.
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Property for sale at 5050 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL, 34786
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