Ad #7627798
MLS #O6401757
Set along Isleworth's signature 12th fairway, this fully
5138 FAIRWAY OAKS DR, Windermere, FL 34786
$5,500,000
4Beds
5Baths
4,330Sqft
0.5Acres
About this property
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 Features
4 Beds
5 Baths
4,330 Sqft
Built in 1994
0.5 Acres
Isleworth Golf and Country Club
On Golf Course
Driveway, Garage, Garage - Attached
Siding: Block, Stucco
Tile Roof
Has Swimming Pool
Has Fireplace
Electric (Heating), Fireplace(s), Natural Gas
$19,599 / yr property tax
Orange County
$14,688 / yr HOA
ISLEWORTH Community
Additional Photos
Contact Information
Monica Lochmandy
Isleworth Realty, LLC
407-230-6888
Location
Listing Agent: Monica Lochmandy (License #: 3237911) 407-230-6888
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
GolfHomes.com
Printed Aug 11, 2026
Photo Gallery
$5,500,000
4
Beds
5
Baths
4,330
Sqft
5138 FAIRWAY OAKS DR, Windermere, FL 34786
By contacting this agent you agree to these Terms and Conditions.
MLS# O6401757
Set along Isleworth's signature 12th fairway, this fully
$5,500,000
5138 FAIRWAY OAKS DR, Windermere, FL 34786
4
Beds
5
Baths
4,330
Sqft
0.5
Acres
$5,500,000
5138 FAIRWAY OAKS DR, Windermere, FL 34786
4 Beds
5 Baths
4,330 Sqft
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.
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Property Details
HOME DETAILS
4 Beds
5 Baths
4,330 Sqft
Built in 1994
0.5 Acres
GOLF COURSE & VIEW
Isleworth Golf and Country Club
On Golf Course
EXTERIOR
Driveway, Garage, Garage - Attached
Siding: Block, Stucco
Tile Roof
Has Swimming Pool
INTERIOR
Has Fireplace
Electric (Heating), Fireplace(s), Natural Gas
FINANCIAL & COMMUNITY
$19,599 / yr property tax
Orange County
$14,688 / yr HOA
ISLEWORTH Community
See More Details
Location
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Ad Statistics
Ad Number
7627798
Viewed
78 times
Listing Status
Active
Added
Apr 25, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Stellar MLS
Source Property ID
O6401757
Listing Agent: Monica Lochmandy (License #: 3237911) 407-230-6888
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Isleworth Realty, LLC 407-876-0111 Listing Site
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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