5138 Fairway Oaks Dr,WINDERMERE, FL 34786
WINDERMERE, FL 34786
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.
Details
| MLS # | O6401757 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| HOA Dues | $3,672 |
| Sub-Type | For-sale |
| Status | Active |
| Year | 1994 |
| Days On Site | 154 |
| Listing Provided By | ISLEWORTH REALTY LLC | Monica Lochmandy |
Features
| Bed(s) | 4 |
|---|---|
| Bath(s) | 5 Total |
| SQ Feet | 4,330 |
| Garage | 3 |
| Pool | Yes |
| Story(s) | 1 |
| Zoning | P-D |
| Acreage | 0.50 |
| Property View | Golf Course, Water |
Taxes
| Property | 19599 |
|---|
Area Information
| State | FL |
|---|---|
| County | Orange |
| City | WINDERMERE |
| Zip Code | 34786 |
| Area | 34786 Windermere |
| Community Name | ISLEWORTH |
| School District | Olympia High |
| Elementary School | Windermere Elem |
| High School | Olympia High |
| Listing VS Median (in ISLEWORTH) | |
Price: $4,999,500 low | high Med: $3,800,000 sqft: 4,330 low | high Med: 5,301 $ / sqft: $1,155 low | high Med: $717 On site: 154 low | high Med: 190 | |
Market Activity 34786
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Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of September 27, 2026 at 12:43:10 AM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
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Learn More About This Property
| State | FL |
|---|---|
| County | Orange |
| City | WINDERMERE |
| Zip Code | 34786 |
| Area | 34786 Windermere |
| Community Name | ISLEWORTH |
| School District | Olympia High |
| Elementary School | Windermere Elem |
| High School | Olympia High |
| Listing VS Median (in ISLEWORTH) | |
Price: $4,999,500 low | high Med: $3,800,000 sqft: 4,330 low | high Med: 5,301 $ / sqft: $1,155 low | high Med: $717 On site: 154 low | high Med: 190 | |
 | $2,200,0002 Chase RdWindermere, FL 34786 |
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
