2540 WINNERS CIRCLE, Kissimmee, FL 34744

• 4 beds |
• 5 baths |
• 3,246 sqft

Property Description

**WELCOME HOME** NO HOA, HALF AN ACRE of land, a PRIVATE POOL, and a full SEPARATE APARTMENT on the main floor – welcome to your next chapter on Winners Circle in the Winners Park community of Kissimmee! EXTERIOR PAINT (2023), NEW WINDOWS (2022), DETACHED AIR CONDITIONED GARAGE (2022), septic tank serviced (2022) – big-ticket items are already started, giving you confidence and flexibility from day one. Situated on an expansive .50 ACRE LOT, this spacious two-story POOL HOME delivers over 3,000 square feet of living space, mature landscaping, a TILE ROOF, long paver driveway, and standout curb appeal. The SCREENED POOL with PAVER DECK creates a private backyard retreat with room to entertain, garden, or just spread out. Inside, the flexible layout is ideal for large households, multi-generational living, or anyone needing versatile space. The full first-floor apartment includes its own kitchen open to a living area, bedroom, and full bath – perfect for in-laws, guests, extended stays, or even creative work from home options! The main home features comfortable formal and family spaces, a well-equipped kitchen with casual dining, and an expansive FLORIDA ROOM complete with a full bath and cozy office space – offering endless possibilities for hobbies, remote work, or additional entertaining. Upstairs, a BONUS/LOFT anchors the remaining bedrooms, while the generous PRIMARY SUITE provides a peaceful escape with an updated private en-suite bath. Car enthusiasts, hobbyists, or entrepreneurs will appreciate the two-car attached garage plus the like-new detached, air-conditioned garage – currently used as a dojo, but easily transformed into a workshop, craft studio, gym, or business space. Updated yet still offering room to personalize, this home offers the rare combination of space, privacy, flexibility, and location. Perfectly situated just off Simpson Road, you will enjoy easy access to the Florida Turnpike, shopping, dining, area lakes, attractions, and world-famous theme parks – all while coming home to a quiet, established neighborhood with no HOA restrictions. Room to grow inside and out. Versatility for today and tomorrow. Schedule your tour today and be the winner on Winners Circle! **Seller may consider buyer concessions if made in an offer**

Listing Status:

Active

Date Added:

February 19, 2026

Data Last Updated:

March 11, 2026 at 7:24AM

Listing Office:

WEMERT GROUP REALTY LLC : 407-743-8356

Listing Agent:

Jenny Wemert : 407-809-1193

MLS ID:

O6382446

Interior

• General: Ceiling Fans(s)Eat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboPrimaryBedroom UpstairsSolid Surface CountersStone CountersWalk-In Closet(s)Window Treatments
• Rooms: Bonus RoomDen/Library/OfficeFamily RoomFlorida RoomFormal Dining Room SeparateFormal Living Room SeparateInterior In-Law Suite w/Private EntryLoft
• Appliances: DishwasherDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasherWater Filtration SystemWater Softener
• Laundry: In Garage
• Flooring: CarpetTile
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: Hurricane ShuttersLightingPrivate MailboxRain GuttersSliding DoorsStorage
• Other Structures: OtherShed(s)WorkshopEnclosedFront PorchRear PorchPatioCovered
• Pool: Auto CleanerGuniteIn GroundLightingScreen Enclosure
• Parking: BoatCurb ParkingDrivewayGarage Door OpenerGolf Cart ParkingGround LevelGuestOn StreetOversizedParking PadRV Access/Parking

Construction

• Roofing: Tile
• Windows: Aluminum FramesBlindsDouble Pane WindowsENERGY STAR Qualified WindowsThermal Windows
• General: BlockStuccoTwoSlab

Location

• Road/Access: Paved
• Originating MLS: Stellar MLS
• County: Osceola

Lot

• Zoning: OR1CWINNERS PARK PB 7 PG 48 LOT 617-25-30-5515-0001-0060

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedFiber OpticsWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple