USAFLWindermereIsleworth5138 Fairway Oaks Dr

5138 Fairway Oaks Dr, Windermere, FL

House

For Sale

Listed price in listed location currency (USD).

$5,500,000

453

MLS® O6401757

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 4330 sqft

Garage Yes

Taxes $19,599

Days Active 0

Lot Size

Approx. Age 1994

Avg. Price Per Sqft $1,270

MLS® Number O6401757

Property Address: 5138 Fairway Oaks Dr, WINDERMERE, FL, 34786

Average square foot calculated using Size range provided by listing agent.

Description

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.

MLS® NumberO6401757

Laundry LevelEnsuite

Central VacNo

FireplaceNo

Acreage

Exterior

GarageYes

Approx. Age1994

Basement

DrivewayCircular Driveway, Garage Door Opener, Garage Faces Side

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Apr 25, 2026List Date

$5,500,000List Price

Aug 17, 2025End Date

$2,500,000Sold Price

Sold

Mar 1, 2025List Date

$2,900,000List Price

Commute

Commute

Starting Address

Destination Address

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