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2540 WINNERS CIRCLE
KISSIMMEE FL 34744 US

$800,000

Active Listing ID O6382446
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4 bed
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5.00 Bath (4 Full , 1 Half)
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Lot: 0.50 Acres
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Single Family Residence

$800,000

Active Listing ID O6382446
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2540 WINNERS CIRCLE **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**

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Property Features

  • Facts
  • Lot Size: 0.50 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Paved, Hurricane Shutters, Lighting, Private Mailbox, Rain Gutters, Sliding Doors, Storage, Pool
  • Floor Covering: Carpet, Tile
  • Roof Type: Tile
  • Heating Fuels: Central, Electric (Heating)
  • Additional Features
  • Pool

School Information

  • School
  • East Lake Elem(Elementary)
  • Neptune Middle (6-8)(MiddleSchool)
  • Tohopekaliga High School(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 800000
  • unparsedaddress: 2540 WINNERS CIRCLE
  • postalcity: KISSIMMEE
  • stateorprovince: FL
  • country: US
  • postalcode: 34744
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.5
  • lotsizeunits: Acres
  • lotsizearea: 0.5
  • livingarea: 3246
  • livingareaunits: Square Feet
  • latitude: 28.307704
  • longitude: -81.340869
  • listagentfullname: Jenny Wemert
  • listagentemail: listingteam@wemertgrouprealty.com
  • listagentkey: 3yd-MFRMLSFL-805527269
  • listagentmlsid: 805527269
  • listagentpreferredphone: 4074128488
  • listagentofficephone: 4074128488
  • listofficekey: 3yd-MFRMLSFL-261014414
  • listagentstatelicense: 3044371
  • listofficemlsid: 261014414
  • disclaimer: Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 2000
  • listingcontractdate: 2026-02-19
  • listagenturl: http://wemertgrouprealty.com
  • countyorparish: Osceola
  • parcelnumber: 17-25-30-5515-0001-0060
  • elementaryschool: East Lake Elem
  • highschool: Tohopekaliga High School
  • appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Water - Softener
  • cooling: Central Air
  • constructionmaterials: Block, Stucco
  • flooring: Carpet, Tile
  • heating: Central, Electric (Heating)
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Boat, Driveway, Garage, Garage - Attached, Golf Cart, Guest, On Street, Oversized, RV
  • roof: Tile
  • waterfrontyn: False
  • interiorfeatures: Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primarybedroom Upstairs, Solid Surface Counters, Stone Counters, Walk-in Closet(s), Window Treatments
  • exteriorfeatures: Paved, Hurricane Shutters, Lighting, Private Mailbox, Rain Gutters, Sliding Doors, Storage, Pool
  • architecturalstyle: Other
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Living Room, Loft
  • otherstructures: Storage
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.340866, 28.307705
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Wemert Group Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"info@wemertgrouprealty.com", "ListBrokerageCity":"Orlando", "ListBrokerageCountry":"US", "ListBrokerageEmail":"mike@wemertgrouprealty.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/MFRMLSFL/e1ecad71f45911e680b20242ac110009/20170221213926388.png", "ListBrokerageName":"Wemert Group Realty", "ListBrokeragePhone":"4074128488", "ListBrokeragePostalCode":"32828", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"650 N Alafaya Trail Suite 105", "ListBrokerageWebsiteUrl":"http://wemertgrouprealty.com", "ListOfficeAddress1":"650 N Alafaya Trl #105", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Orlando", "ListOfficeCountry":"US", "ListOfficeEmail":"mike@wemertgrouprealty.com", "ListOfficePostalCode":"32828", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence - KISSIMMEE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/2540-Winners-Cir_Kissimmee_FL_34744_M57586-41324?f=listhub&s=MFRMLSFL&m=O6382446&c=rexren", "MLSModificationTimestamp":"2026-02-19T17:02:11Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":12, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":3688, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 2/20/2026 12:41:08 AM GMT
Source Updated Date: 2/20/2026 6:50:30 PM GMT

Courtesy of: Jenny Wemert, WEMERT GROUP REALTY LLC, listingteam@wemertgrouprealty.com

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.