To schedule a showing of 5243 Isleworth Country Club Drive, Windermere, Florida, Call David Shippey at 863-521-4517 TODAY!
$5,100,000 | 4 beds | 5 full baths | 1 half baths | 6,424 sqft
Windermere, FL 34786
- 4Beds
- 6.00Total Baths
- 5 Full, 1 HalfBaths
- 6,424SqFt
- 1992Year Built
- 0.51Acres
- MLS# O6348067
- Residential
- SingleFamilyResidence
- Active
- Approx Time on Market8 months, 11 days
- Area34786 - Windermere
- CountyOrange
- Subdivision Isleworth
Overview
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major spare no expense remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chefs kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
Agriculture / Farm
Association Fees / Info
Community Features: BoatFacilities, Golf, GolfCartsOk, Park, WaterAccess, Gated, StreetLights
Pets Allowed: Yes
Hoa Frequency Rate: 3672
Association: Yes
Association Amenities: Gated, Park, Security
Hoa Fees Frequency: Quarterly
Association Fee Includes: AssociationManagement, RoadMaintenance, Security
Bathroom Info
Total Baths: 6.00
Fullbaths: 5
Building Info
Window Features: Blinds, InsulatedWindows, Shutters, ThermalWindows, WindowTreatments
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Custom, SpanishMediterranean
Pool Features: Heated, InGround, SaltWater
Patio: RearPorch, Covered, Porch
Pool Private: Yes
Exterior Features: FrenchPatioDoors, SprinklerIrrigation, Lighting, OutdoorKitchen, Storage
Fees / Restrictions
Financial
Original Price: $5,325,000
Disclosures: CovenantsRestrictionsDisclosure
Fencing: Fenced, Other
Garage / Parking
Parking Features: CircularDriveway, GolfCartGarage, GarageFacesSide
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: Gas, LivingRoom, Outside
Fireplace: Yes
Floors: Carpet, Marble, PorcelainTile, Wood
Levels: Two
Laundry Features: Inside
Interior Features: WetBar, BuiltInFeatures, CeilingFans, CrownMolding, CentralVacuum, CofferedCeilings, EatInKitchen, HighCeilings, LivingDiningRoom, MainLevelPrimary, OpenFloorplan, StoneCounters, VaultedCeilings, WalkInClosets, WoodCabinets, WindowTreatments, Attic, Loft
Appliances: BarFridge, Dryer, Dishwasher, ExhaustFan, ElectricWaterHeater, Disposal, IceMaker, Microwave, Range, Refrigerator, RangeHood, WineRefrigerator, Washer
Lot Info
Direction Remarks: From I-4, take Conroy Road West. From Apopka Vineland Rd and Conroy Windermere Roads, go west on Conroy Windermere into Windermere. Left into Isleworth. After guard house, go straight on Isleworth Country Club Drive. House is on the left.
Lot Size Units: Acres
Lot Size Acres: 0.51
Lot Sqft: 22,199
Vegetation: Oak
Lot Desc: Flat, Level, OutsideCityLimits, OnGolfCourse, BuyerApprovalRequired, Landscaped
Misc
Other
Other Structures: OutdoorKitchen
Special Conditions: None
Security Features: SecuritySystemOwned, SecuritySystem, ClosedCircuitCameras, SmokeDetectors, GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 16
Class Type: SingleFamilyResidence
Property Sub Type: SingleFamilyResidence
Construction Materials: Block, Stucco
Stories: 2
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 11
Sqft Info
Sqft: 6,424
Bulding Area Sqft: 7,246
Living Area Units: SquareFeet
Living Area Source: Estimated
Tax Info
Tax Year: 2,024
Tax Lot: 231
Tax Legal Description: ISLEWORTH 16/118 LOT 231
Tax Block: 2
Tax Annual Amount: 50194
Tax Book Number: 16-118
Unit Info
Utilities / Hvac
Heating: Central, Electric, Zoned
Water Source: Public
Sewer: SepticTank
Cool System: CentralAir, Zoned, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableConnected, NaturalGasConnected, UndergroundUtilities, WaterConnected
Waterfront / Water
View: Yes
Water Body Name: LAKE CHASE
View: GolfCourse, Lake, Water
Directions
From I-4, take Conroy Road West. From Apopka Vineland Rd and Conroy Windermere Roads, go west on Conroy Windermere into Windermere. Left into Isleworth. After guard house, go straight on Isleworth Country Club Drive. House is on the left.This listing courtesy of Stockworth Realty Group
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MLS IDX data last updated on 06-20-2026 7:46 PM EST.
If you have any questions on 5243 Isleworth Country Club Drive, Windermere, Florida, please call David Shippey at 863-521-4517.
MLS# O6348067 located at 5243 Isleworth Country Club Drive, Windermere, Florida is brought to you by David Shippey REALTOR®
5243 Isleworth Country Club Drive, Windermere, Florida has 4 Beds, 5 Full Bath, and 1 Half Bath.
The MLS Number for 5243 Isleworth Country Club Drive, Windermere, Florida is O6348067.
The price for 5243 Isleworth Country Club Drive, Windermere, Florida is $5,100,000.
The status of 5243 Isleworth Country Club Drive, Windermere, Florida is Active.
The subdivision of 5243 Isleworth Country Club Drive, Windermere, Florida is Isleworth.
The home located at 5243 Isleworth Country Club Drive, Windermere, Florida was built in 2026.