Property
ActiveResidential
1/40
$3,390,000

5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL 34786
4
Beds
5
Baths
3,365
SqFt
0.52
Acres
STELLAR
#O6372348
Updated: Feb 25, 2026, 9:23pm

Property Description

Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in the heart of Windermere, Florida.

The foyer with groin ceiling is light and bright as natural light floods into the home from the glass entryway. Arched details abound in the entrance and this staple in Mediterranean design is carried throughout the estate. Two steps down into the sunken formal living room, the gas fireplace is the centerpiece featuring an artistic stone slab above the hearth and framed by wall-to-wall stacked stone. Completing the space are four large arched windows, two arched doors providing access to the back garden and a built-in dry bar. Situated between the family room and formal living room, and serviced by the nearby kitchen, the formal dining room offers the same illumination of natural sunlight from two large arched windows.

The kitchen features new KitchenAid stainless steel appliances, a NXR Pro gas range and built-in 40 bottle Euro Cave wine fridge. The custom cabinetry provides ample storage and tastefully pairs in a dark grey-brown tone with the white tile backsplash, multi-tonal grey to white tile range hood and marble counters with soft neutral veins. The custom cabinetry continues seamlessly into the family room with built-in entertainment center.

Down the hall from the kitchen and family room are the guest rooms. The first features an ensuite bathroom and the other two bedrooms are serviced by the hall bath with dual sinks. The hall bath also provides access to the patio and serves as the pool bath.

Situated on the opposite end of the home, we find the primary suite, powder bath off the foyer and a flex room. The primary is airy and bright with arched windows, stacked stone fireplace and a dazzling chandelier. The suite features two separate bathrooms – one with walk-in shower and the second with free-standing soaking tub. The walk-in closet offers a warm cedar wood ceiling and custom built-ins. The flex room proposes many uses whether it be an office, nursery, gym, den or library.

This stunning property offers a seamless blend of indoor-outdoor living boasting a covered patio with fireplace, open-air pool with spa and views of the fairway. Rounding out the estate is a welcoming circular driveway that extends to the rear motor court with two-car garage plus golf cart parking. Whether hosting or unwinding, this home elevates every moment.
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Included Appliances
DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator

Property Details

Highlights
View
Yes
Interior
Additional Rooms
Den/Library/OfficeFormal Dining Room SeparateFormal Living Room Separate
Appliances
DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator
Bathrooms Total Decimal
4.5
Building Area Total
4843
Cooling
Central AirZoned
Fireplace Features
Living RoomOutsideMaster Bedroom
Flooring
Porcelain Tile
Furnished
Negotiable
Heating
CentralElectricZoned
Interior Features
Built-in FeaturesCentral VacuumEating Space In KitchenHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersWalk-In Closet(s)Window Treatments
Laundry Features
InsideLaundry Room
Living Area
3365
Rooms Total
13
Security Features
Gated Community
Window Features
BlindsDrapesRodsShadesTinted Windows
Construction
Building Area Source
Public Records
Building Area Units
Square Feet
Construction Materials
BlockStucco
Direction Faces
Southeast
Foundation Details
Block
Levels
One
Living Area Source
Public Records
Living Area Units
Square Feet
Roof
TileConcrete
Year Built
1987
Site & Exterior
Covered Spaces
2
Exterior Features
Irrigation SystemLightingRain GuttersSliding DoorsSprinkler Metered
Fencing
Fenced
Flood Zone Code
X
Garage Dimensions
31x27
Garage Spaces
2
I D X Participation
Yes
Lot Features
On Golf CourseIn CountyLandscaped
Lot Size Acres
0.52
Lot Size Area
22514
Lot Size Dimensions
190 x 151 x 128 x 145
Lot Size Square Feet
22514
Lot Size Units
Square Feet
Open Parking
Yes
Parking Features
Golf Cart ParkingCircular DrivewayDrivewayGarage Door OpenerGarage Faces RearOversized
Patio And Porch Features
CoveredRear Porch
Pool Features
GuniteTile
Public Survey Range
28
Public Survey Section
16
Road Frontage Type
Private RoadStreet Paved
Road Responsibility
Private Maintained Road
Road Surface Type
PavedAsphalt
Sewer
Septic Tank
Spa Features
In Ground
Total Acreage
1/2 to less than 1
Utilities
BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPhone AvailablePublicSprinkler MeterStreet LightsUnderground UtilitiesWater Connected
Vegetation
Mature LandscapingOak Trees
View
Golf Course
Water Source
Public
Waterfront Features
LakeWaterfront
Zoning
P-D
Financials
Amenities Additional Fees
Membership to Isleworth Golf & Country Club offers amenities at a separate charge.
Association Fee
3129
Association Fee Frequency
Quarterly
Association Fee Includes
24-Hour GuardCable TVEscrow Reserves FundMaintenance GroundsMaintenance RepairsPrivate RoadSecurity
Calculated List Price By Calculated Sq Ft
1007.43
Contract Status Change Date
2026-01-10
Current Price
3390000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
7 Months
Monthly H O A Amount
1043
Ownership
Fee Simple
Parcel Number
162328389900410
Public Survey Township
23
Tax Annual Amount
28793
Tax Block
00
Tax Book Number
16/118
Tax Legal Description
ISLEWORTH 16/118 LOT 41
Tax Lot
41
Tax Year
2025
Total Annual Fees
12516
Total Monthly Fees
1043

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
Per Isleworth Community Association (ICA)
Association Amenities
Basketball CourtCable TVFence RestrictionsGatedOptional Additional FeesPlaygroundSecurityVehicle Restrictions
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 RampLakeWater AccessWaterfrontAssociation Recreation - OwnedClubhouseCommunity MailboxFitness CenterGated Community - GuardGolf Carts OKGolfIrrigation-Reclaimed WaterPlaygroundPoolRestaurantSpecial Community RestrictionsTennis Court(s)
Lease Restrictions
Yes
M L S Area Major
34786 - Windermere
Pet Restrictions
Breed restrictions and leash laws per Orange County
Pets Allowed
Breed RestrictionsCats OKDogs OKYes
Subdivision Name
ISLEWORTH
Schools
Ratings
Elementary
Windermere Elem
Middle
Chain of Lakes Middle
High
Olympia High
Listing provided courtesy of STELLAR via IDX. Updated: Feb 25, 2026, 9:23pm.
Toni Cafferty

Listing Agent

COMPASS FLORIDA LLC

Call Agent