5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

bedrooms 4
bathrooms 5
|House
AUD $7,181,382
USD $4,999,500
Published on: 26 Apr 2026
Last updated on: 30 Sep 2026
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
+51
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
  • 51
Property ID: 110107571421
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Residential, WINDERMERE, FL

5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786
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 Details

Basic Info

Property Type
House
Listing Status
Active
Land Size
2,023.43 m2
Building Size
402.27 m2
Year Built
1994
Rooms
4 bedroom(s), 5 bathroom(s)
Architecture Style
Other
Num Floors
1
County
Orange
Parcel ID
16-23-28-3899-01-080
Provider
Stellar MLS
Subdivision
ISLEWORTH
Brokerage Office Name
Isleworth Realty, LLC
Brokerage Office Phone
(407) 876-0111
Neighbourhoods
ISLEWORTH
Address
5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

Nearby Schools

TypeSchool nameDistrict name
HighOlympia HighNot available
ElementaryWindermere ElemNot available
MiddleChain of Lakes MiddleNot available
JuniorhighChain of Lakes MiddleNot available

Tax History

YearTax amount
2025USD $19599AUD $28,152*

*Converted price in your currency provided by Open Exchange Rates. Exchange rates are subject to continuous change. Neither realestate.com.au nor its affiliates guarantee that the conversion reflects current conversion rates and are not responsible for any inaccuracies. realestate.com.au recommends that you independently verify any information before relying on it.

Contact Agent
Monica Lochmandy
ISLEWORTH REALTY LLC
9350 Conroy Windermere Rd , Windermere, FL 34786
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Monica Lochmandy
9350 Conroy Windermere Rd , Windermere, FL 34786
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      Property ID: 110107571421

      Original Property ID: 3yd-MFRMLSFL-O6401757
      Data provided by Stellar MLS, MLS #: O6401757
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