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$5,500,000 - 5138 Fairway Oaks Dr, WINDERMERE

4
Bedrooms
5
Baths
4,330
SQ. Feet
0.5
Acres

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.

Essential Information

  • 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
  • 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

  • Days on Market:
    88
  • Zoning:
    P-D

Listing Details

  • Listing Office:
    Isleworth Realty Llc

Listing information courtesy of Isleworth Realty Llc.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on July 23rd, 2026 at 11:24am EDT.