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$5,500,000
New Listing

5138 FAIRWAY OAKS DR
WINDERMERE, FL 34786

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
5
Full Baths
4,330
SqFt
$1,270
/SqFt
1994
Built
Subdivision:
ISLEWORTH
County:
Orange
Call Now: (561) 935-3331
Is this the listing for you? We can help make it yours.
(561) 935-3331
5138 FAIRWAY OAKS DR5138 FAIRWAY OAKS DR5138 FAIRWAY OAKS DR5138 FAIRWAY OAKS DR
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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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Listing Snapshot
Price 
$5,500,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
4,330 sqft
Total Baths 
5
Full Baths 
5
Partial Baths 
N/A
Lot Size 
0.5 Acres
Year Built 
1994
MLS® Number 
O6401757
Status 
Active
Property Tax 
$19,599.37
HOA/Condo/Coop Fees 
$1,224 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
29 minutes agoListing updated with changes from the MLS®
5 hours agoListing first seen on site
General Features
Acres 
0.5
Attached Garage 
Yes
Direction Faces 
Northeast
Foundation 
Slab
Garage 
Yes
Garage Spaces 
3
Levels 
One
Parking 
Circular DrivewayGarage Door OpenerGarage Faces SideAttached
Pets 
Breed Restrictions
Property Sub Type 
Single Family Residence
Security 
Gated CommunitySecurity Gate
Sewer 
Septic Tank
SqFt Total 
5911
Style 
Traditional
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedWater Connected
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanFreezerIce MakerMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
Family Room
Flooring 
Tile
Furnished 
Furnished
Heating 
ElectricNatural Gas
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenStone CountersWalk-In Closet(s)
Laundry Features 
InsideLaundry Room
Spa 
Yes
Bathroom 2 
Level - FirstDescription - Room4
Bathroom 3 
Level - FirstDescription - Room6
Bathroom 4 
Level - FirstDescription - Room8
Bedroom 2 
Level - FirstDescription - Room3
Bedroom 3 
Level - FirstDescription - Room5
Bedroom 4 
Level - FirstDescription - Room7
Dining Room 
Level - FirstDescription - Room12
Family Room 
Level - FirstDescription - Room10
Kitchen 
Level - FirstDescription - Room9
Living Room 
Level - FirstDescription - Room11
Master Bathroom 
Level - FirstDescription - Room2
Master Bedroom 
Level - FirstDescription - Room1
Office 
Level - FirstDescription - Room13
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Exterior Features
Construction Details 
BlockStucco
Exterior 
LightingRain Gutters
Fencing 
Other
Lot Features 
LandscapedOn Golf Course
Patio And Porch 
CoveredRear Porch
Pool Features 
HeatedIn GroundPrivate
Private Pool 
Yes
Roof 
Tile
Spa 
Yes
Spa Features 
HeatedIn Ground
View 
LakePondWaterGolf Course
Waterfront Features 
LAKE BRENDA AKA HOURGLASS POND
Waterview 
LakePondWaterGolf Course
Community Features
Association Amenities 
Cable TVGatedPlaygroundSecurity
Association Dues 
3672
Community Features 
GatedPlaygroundStreet Lights
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Quarterly
MLS Area 
34786 - Windermere
Roads 
Paved
Township 
23
Schools
School District
Unknown
Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High
Listing courtesy of ISLEWORTH REALTY LLC (407) 230-6888



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-04-25 01:41 PM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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