$4,999,500
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
ActiveProperty details
About this home
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.
Property records
Public records from the county assessor.
Recent sales
Keep exploring
Listings courtesy of Stellar MLS as distributed by MLS GRID. MLS #MFR788547244. Listing brokerage: ISLEWORTH REALTY LLC. Status: Active.
IDX information is provided exclusively for consumers' personal, non-commercial use, may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and is deemed reliable but not guaranteed by MLS GRID. Properties displayed may be listed or sold by various participants in the MLS.
Based on information submitted to the MLS GRID as of November 7, 2026 at 3:30 PM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Information deemed reliable but not guaranteed. All listings are subject to prior sale, change, or withdrawal. Neither the listing broker(s) nor Vectis by Wolliz shall be responsible for any typographical errors, misinformation, or misprints. © 2026 Vectis by Wolliz, Inc.
More homes in WINDERMERE
