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Property for sale at 5138 FAIRWAY OAKS DR, WINDERMERE, FL, 34786
Property for sale at 5138 FAIRWAY OAKS DR, WINDERMERE, FL, 34786
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5138 Fairway Oaks DrWindermere, FL, 34786

4beds
5baths
4,330sqft
Single Family Residence
Built in 1994
$3,672 Quarterly HOA Fee
$4,999,500
For sale
$5,500,000−$500,500 (9%)Reduced Aug 14, 2026
Price per sqft
$1,155
Days on market
166
Listed Apr 25, 2026
MLS #O6401757Updated Sep 16, 2026

About this property

Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

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Property details

Property type
Single Family Residence
Street address
5138 Fairway Oaks Dr
City
Windermere
State
FL
ZIP code
34786
Year built
1994
New construction
No
Faces
Northeast
Rooms
13
Living area
4,330 sqft
Total building area
5,911 sqft
Architectural style
Traditional
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

Asking price reduced by $500,500 (9.1%) since first listed.

EventPrice
Price reducedMLS #O6401757$4,999,500Change: −9.1%−$500,500
Listed for saleMLS #O6401757$5,500,000
SoldMLS #O6282470$2,500,000
Price reducedMLS #O6282470$2,900,000Change: −9.4%−$300,000
History may be incomplete.
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Property for sale at 5138 FAIRWAY OAKS DR, WINDERMERE, FL, 34786
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