$5,500,000

5138 FAIRWAY OAKS DR, Windermere, FL 34786

Active
4
Beds
5
Baths
4,330
Sq Ft
$1,270
Per Sq Ft
1994
Built
10
Days Listed
3
Garage
0.50
Acres

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.

Facts & Features

Interior
Bedrooms4
Full Bathrooms5
Half Bathrooms0
Interior Sq Ft4,330
Total Structure Area5,911 sqft
FireplaceYes
FlooringTile
HeatingElectric, Natural Gas
CoolingCentral Air, Zoned
AppliancesBar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Fre
LaundryCorridor Access, Inside, Laundry Room
Interior FeaturesBuilt-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Famil
Property
Construction
Utilities
Community & HOA
Financial & Listing Details

Rooms

Room types: Primary Bedroom, Primary Bathroom, Bedroom 2, Bathroom 2, Bedroom 3, Bathroom 3, Bedroom 4, Bathroom 4, Kitchen, Family Room, Living Room, Dining Room, Office

Primary Bedroom
LevelFirst
FlooringTile
Primary Bathroom
LevelFirst
FlooringTile
Bedroom 2
LevelFirst
FlooringTile
Bathroom 2
LevelFirst
FlooringTile
Bedroom 3
LevelFirst
FlooringTile
Bathroom 3
LevelFirst
FlooringTile
Bedroom 4
LevelFirst
FlooringTile
Bathroom 4
LevelFirst
FlooringTile
Kitchen
LevelFirst
FlooringTile
Family Room
LevelFirst
FlooringTile
Living Room
LevelFirst
FlooringTile
Dining Room
LevelFirst
FlooringTile
Office
LevelFirst
FlooringTile

Schools

ElementaryWindermere Elem
High SchoolOlympia High A
School assignments and grades are informational — verify boundaries with the school district before purchasing.

Price History

Apr 25, 2026 Listed $5,500,000

Listed by ISLEWORTH REALTY LLC · MLS# O6401757

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Properties displayed may be listed or sold by various participants in the MLS


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. Data deemed reliable but not guaranteed. Last updated: 2026-05-05.
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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Florida Property Finder · LPT Realty, LLC
Mike Valdes
Mike Valdes
Florida Property Finder · LPT Realty
(813) 548-5618
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