Property
ActiveResidential
1/51
$5,500,000

5138 FAIRWAY OAKS DR

Windermere, FL 34786
4
Beds
5
Baths
4,330
SqFt
0.5
Acres
STELLAR
#O6401757
Updated: May 5, 2026, 1:08pm

Property 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.
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Included Appliances
Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanFreezerIce MakerMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator

Property Details

Highlights
View
Yes
Interior
Appliances
Bar FridgeDishwasherDisposalDryerElectric Water HeaterExhaust FanFreezerIce MakerMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator
Bathrooms Total Decimal
5
Building Area Total
5911
Cooling
Central AirZoned
Fireplace Features
Family Room
Flooring
Porcelain Tile
Furnished
Furnished
Heating
ElectricNatural Gas
Interior Features
Built-in FeaturesCeiling Fan(s)Crown MoldingEating Space In KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboSolid Surface CountersStone CountersThermostatWalk-In Closet(s)
Laundry Features
Corridor AccessInsideLaundry Room
Living Area
4330
Rooms Total
13
Security Features
Gated CommunitySecurity Gate
Construction
Architectural Style
Traditional
Building Area Source
Public Records
Building Area Units
Square Feet
Construction Materials
BlockStucco
Direction Faces
Northeast
Foundation Details
Slab
Levels
One
Living Area Source
Public Records
Living Area Units
Square Feet
Roof
Tile
Year Built
1994
Site & Exterior
Additional Water Information
The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
Covered Spaces
3
Exterior Features
French DoorsLightingRain Gutters
Fencing
Other
Flood Zone Code
X
Garage Spaces
3
I D X Participation
Yes
Lot Features
LandscapedOn Golf CourseOversized Lot
Lot Size Acres
0.5
Lot Size Area
21939
Lot Size Square Feet
21939
Lot Size Units
Square Feet
Open Parking
Yes
Parking Features
Circular DrivewayGarage Door OpenerGarage Faces Side
Patio And Porch Features
CoveredRear Porch
Pool Features
DeckHeatedIn Ground
Public Survey Range
28
Public Survey Section
16
Road Surface Type
Paved
Sewer
Septic Tank
Spa Features
HeatedIn Ground
Total Acreage
1/2 to less than 1
Utilities
Cable ConnectedElectricity ConnectedFiber OpticsNatural Gas ConnectedStreet LightsWater Connected
View
Golf CourseWater
Water Body Name
LAKE BRENDA AKA HOURGLASS POND
Water Source
Public
Water View
Yes
Zoning
P-D
Financials
Amenities Additional Fees
Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
Association Fee
3672
Association Fee Frequency
Quarterly
Association Fee Includes
24-Hour GuardCable TVEscrow Reserves FundInternetMaintenance GroundsPrivate RoadSecurity
Calculated List Price By Calculated Sq Ft
1270.21
Contract Status Change Date
2026-04-25
Current Price
5500000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
8-12 Months
Monthly H O A Amount
1224
Ownership
Fee Simple
Parcel Number
162328389901080
Public Survey Township
23
Tax Annual Amount
19599.37
Tax Block
01
Tax Book Number
16/118
Tax Legal Description
ISLEWORTH 16/118 LOT 108
Tax Lot
108
Tax Year
2025
Total Annual Fees
14688
Total Monthly Fees
1224

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
Per Isleworth Community Association (ICA)
Association Amenities
Cable TVGatedPlaygroundSecurity
Association Approval Required
Yes
Association Email
dan.oconnell@Isleworth.com
Association Fee Requirement
Required
Association Name
Dan O’Connell
Association Phone
407-909-2071
Community Features
Community Boat RampWater AccessBuyer Approval RequiredCommunity MailboxGated Community - GuardGolf Carts OKPlayground
M L S Area Major
34786 - Windermere
Pet Restrictions
Per Orange County breed restrictionsnumber limits and leash laws.
Pets Allowed
Breed Restrictions
Subdivision Name
ISLEWORTH
Schools
Ratings
Elementary
Windermere Elem
Middle
Chain of Lakes Middle
High
Olympia High
Listing provided courtesy of STELLAR via IDX. Updated: May 5, 2026, 1:08pm.
Monica Lochmandy

Listing Agent

ISLEWORTH REALTY LLC

Call Agent