5138 Fairway Oaks Dr, WINDERMERE, FL

$5,500,000

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4

Beds

5

Baths

4,330

Square feet

0.50

Acres

About 5138 Fairway Oaks Dr

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.

Features of 5138 Fairway Oaks Dr

MLS® # O6401757
Price $5,500,000
Bedrooms 4
Bathrooms 5.00
Full Baths 5
Square Footage 4,330
Acres 0.50
Year Built 1994
Type Residential
Sub-Type Single Family Residence
Style Traditional
Status Active

Community Information

Address 5138 Fairway Oaks Dr
Area Windermere
Subdivision ISLEWORTH
City WINDERMERE
County Orange
State FL
Zip Code 34786

Amenities

Amenities Cable TV, Gated, Playground, Security
Parking Circular Driveway, Garage Door Opener, Garage Faces Side
# of Garages 3
View Golf Course, Water
Is Waterfront No
Has Pool Yes

Interior

Interior Features Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
Appliances Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Heating Electric, Natural Gas
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Family Room

Exterior

Exterior Features French Doors, Lighting, Rain Gutters
Lot Description Landscaped, On Golf Course, Oversized Lot
Roof Tile
Foundation Slab

School Information

Elementary Windermere Elem
Middle Chain of Lakes Middle
High Olympia High

Additional Information

Date Listed April 25th, 2026
Days on Market 80
Zoning P-D
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeISLEWORTH REALTY LLC

Listing Map

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