5050 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL 34786

• 4 beds |
• 5 baths |
• 3,365 sqft

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.

Listing Status:

Active

Date Added:

January 10, 2026

Data Last Updated:

February 9, 2026 at 2:24PM

Listing Office:

COMPASS FLORIDA LLC : 407-203-9441

Listing Agent:

Toni Cafferty : 904-449-2184

MLS ID:

O6372348

Interior

• General: Built-in FeaturesCentral VaccumEat-in KitchenHigh CeilingsKitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersWalk-In Closet(s)Window Treatments
• Rooms: Den/Library/OfficeFormal Dining Room SeparateFormal Living Room Separate
• Appliances: DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator
• Laundry: InsideLaundry Room
• Flooring: Tile
• A/C: Central AirZoned
• Heating: CentralElectricZoned
• Fireplace: Living RoomOutsidePrimary BedroomFireplace

Exterior

• General: LightingRain GuttersSliding DoorsSprinkler MeteredIn Ground
• Other Structures: Rear PorchCovered
• Pool: GuniteTile
• Parking: Golf Cart ParkingCircular DrivewayDrivewayGarage Door OpenerGarage Faces RearOversized

Construction

• Roofing: TileConcrete
• Windows: BlindsDrapesRodsShadesTinted Windows
• General: BlockStuccoOneBlock

Location

• Road/Access: Asphalt
• HOA Amenities: Basketball CourtCable TVFence RestrictionsGatedOptional Additional FeesPlaygroundSecurityVehicle RestrictionsGuard - 24 HourCable TVEscrow Reserves FundMaintenance GroundsMaintenancePrivate RoadSecurity3129.0Quarterly
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: P-DISLEWORTH 16/118 LOT 4116-23-28-3899-00-410
• View: Golf Course
• Fencing: Fenced

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPhone AvailablePublicSprinkler MeterUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple