To schedule a showing of 5050 Isleworth Country Club Drive, Windermere, Florida, Call David Shippey at 863-521-4517 TODAY!
$3,690,000 | 4 beds | 4 full baths | 1 half baths | 3,365 sqft
Windermere, FL 34786
- 4Beds
- 5.00Total Baths
- 4 Full, 1 HalfBaths
- 3,365SqFt
- 1987Year Built
- 0.52Acres
- MLS# O6372348
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market5 months, 11 days
- Area34786 - Windermere
- CountyOrange
- Subdivision Isleworth
Overview
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.
Agriculture / Farm
Association Fees / Info
Community Features: BoatFacilities, Clubhouse, CommunityMailbox, Fitness, Golf, GolfCartsOk, Lake, Playground, Pool, RecreationArea, Restaurant, TennisCourts, Waterfront, WaterAccess, Gated, StreetLights
Pets Allowed: BreedRestrictions, CatsOk, DogsOk, Yes
Hoa Frequency Rate: 3129
Association: Yes
Association Amenities: BasketballCourt, Gated, Playground, Security, CableTv
Hoa Fees Frequency: Quarterly
Association Fee Includes: CableTv, MaintenanceGrounds, MaintenanceStructure, ReserveFund, RoadMaintenance, Security
Bathroom Info
Total Baths: 5.00
Fullbaths: 4
Building Info
Window Features: Blinds, Drapes, Rods, TintedWindows, WindowTreatments
Roof: Concrete, Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Pool Features: Gunite, Tile, Community
Patio: RearPorch, Covered
Pool Private: Yes
Exterior Features: SprinklerIrrigation, Lighting, RainGutters
Fees / Restrictions
Financial
Original Price: $3,975,000
Fencing: Fenced
Garage / Parking
Parking Features: CircularDriveway, Driveway, Garage, GolfCartGarage, GarageDoorOpener, Oversized, GarageFacesRear
Attached Garage: Yes
Garage: Yes
Green / Env Info
Green Water Conservation: WaterRecycling
Interior Features
Fireplace Desc: LivingRoom, PrimaryBedroom, Outside
Fireplace: Yes
Floors: PorcelainTile
Levels: One
Spa: Yes
Laundry Features: Inside, LaundryRoom
Interior Features: BuiltInFeatures, CentralVacuum, EatInKitchen, HighCeilings, KitchenFamilyRoomCombo, MainLevelPrimary, StoneCounters, WalkInClosets, WoodCabinets, WindowTreatments, SeparateFormalDiningRoom, SeparateFormalLivingRoom
Appliances: Dryer, Dishwasher, Disposal, GasWaterHeater, Microwave, Range, Refrigerator, RangeHood, WaterSoftener, TanklessWaterHeater, WineRefrigerator, Washer
Spa Features: InGround
Lot Info
Direction Remarks: I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.
Lot Size Units: Acres
Lot Size Acres: 0.52
Lot Sqft: 22,514
Est Lotsize: 190x151x128x145
Vegetation: Oak
Lot Desc: OutsideCityLimits, OnGolfCourse, PrivateRoad, Landscaped
Misc
Other
Equipment: IrrigationEquipment
Special Conditions: None
Security Features: GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 16
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 1
Foundation: Block
Human Modified: Yes
Room Info
Total Rooms: 13
Sqft Info
Sqft: 3,365
Bulding Area Sqft: 4,843
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 41
Tax Legal Description: ISLEWORTH 16/118 LOT 41
Tax Block: 00
Tax Annual Amount: 28793
Tax Book Number: 16/118
Unit Info
Utilities / Hvac
Heating: Central, Electric, Zoned
Water Source: Public
Sewer: SepticTank
Cool System: CentralAir, Zoned
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityConnected, NaturalGasConnected, HighSpeedInternetAvailable, MunicipalUtilities, PhoneAvailable, UndergroundUtilities, WaterConnected
Waterfront / Water
View: Yes
View: GolfCourse
Directions
I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive, home is on the right.This listing courtesy of Compass Florida Llc
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identify prospective properties consumer may be interested in purchasing. Any information relating
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program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.
MLS IDX data last updated on 06-20-2026 7:46 PM EST.
If you have any questions on 5050 Isleworth Country Club Drive, Windermere, Florida, please call David Shippey at 863-521-4517.
MLS# O6372348 located at 5050 Isleworth Country Club Drive, Windermere, Florida is brought to you by David Shippey REALTOR®
5050 Isleworth Country Club Drive, Windermere, Florida has 4 Beds, 4 Full Bath, and 1 Half Bath.
The MLS Number for 5050 Isleworth Country Club Drive, Windermere, Florida is O6372348.
The price for 5050 Isleworth Country Club Drive, Windermere, Florida is $3,690,000.
The status of 5050 Isleworth Country Club Drive, Windermere, Florida is Active.
The subdivision of 5050 Isleworth Country Club Drive, Windermere, Florida is Isleworth.
The home located at 5050 Isleworth Country Club Drive, Windermere, Florida was built in 2026.