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51 photos

$4,999,500

5138 FAIRWAY OAKS DR
WINDERMERE, FL 34786
Listed by Monica Lochmandy · ISLEWORTH REALTY LLC
Bedrooms
4
Bathrooms
5
Living area
4,330 sqft
Year built
1994

About this home

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.

Highlights

Private poolFireplace

Property details

MLS #
MFRO6401757
Property type
Single Family Residence
Subdivision
ISLEWORTH
Status
Active
Days on market
111
On market date
April 25, 2026
Stories
N/A
Total bathrooms
5
Garage spaces
3
Parking spaces
N/A
Lot size
0.5 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

ElementaryCharter
CENTRAL FLORIDA POLYTECHNIC ACADEMY
1.37 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
Not yet rated
Local Score not yet available for this school
Enrollment
0
District
ORANGE
Middle
CHAIN OF LAKES MIDDLE
1.59 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,108
Student:teacher ratio
20.1:1
District
ORANGE
High
OLYMPIA HIGH
1.76 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,878
Student:teacher ratio
24.8:1
District
ORANGE

Mortgage calculator

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Est. monthly payment
$30,258/mo
$999,900 down
$3,999,600 loan
Principal & interest$25,941
Property tax (est.)$4,166
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 14 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.