5050 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL 34786

• 4 beds |
• 5 baths |
• 3,365 sqft

Property Description

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

Listing Status:

Active

Date Added:

September 4, 2026

Data Last Updated:

September 28, 2026 at 9:21PM

Listing Office:

COMPASS FLORIDA LLC : 407-203-9441

Listing Agent:

Toni Cafferty : 904-449-2184

Contact:

407-203-9441

MLS ID:

O6438618

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 GuttersSprinkler MeteredIn Ground
• Other Structures: Rear PorchCovered
• Pool: GuniteTile
• Parking: Circular DrivewayDrivewayGarage Door OpenerGarage Faces RearGolf Cart ParkingOversized

Construction

• Roofing: ConcreteTile
• Windows: BlindsDrapesRodsShadesTinted Windows
• General: BlockStuccoOneBlock

Location

• Road/Access: Asphalt
• HOA Amenities: Basketball CourtCable TVFence RestrictionsGatedOptional Additional FeesPlaygroundSecurityVehicle RestrictionsGuard - 24 HourCable TVEscrow Reserves FundMaintenance GroundsMaintenancePrivate RoadSecurity3672.0Quarterly
• 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