Under contract-accepting backup offers. Virtually Staged. **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**
Property Details
Price:
$650,000
MLS #:
O6382446
Status:
Active Under Contract
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINNERS PARK
Neighborhood:
34744kissimmee
Listed Date:
Feb 19, 2026
Finished Sq Ft:
3,246
Total Sq Ft:
3,710
Lot Size:
21,824 sqft / 0.50 acres (approx)
Year Built:
2000
See this Listing
Schools
Elementary School:
East Lake Elem
Middle School:
Neptune Middle (6-8)
High School:
Tohopekaliga High School
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Filtration System, Water Softener
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Surface Counters, Stone Counters, Walk-In Closet(s), Window Treatments
Laundry Features
In Garage
Levels
Two
Exterior
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
4
Direction Faces
North
Exterior Features
Hurricane Shutters, Lighting, Private Mailbox, Rain Gutters, Sliding Doors, Storage
Garage Spaces
4
Lot Features
Cul-De-Sac, Landscaped, Oversized Lot, Street Dead-End
Open Parking YN
1
Other Structures
Other, Shed(s), Workshop
Parking Features
Boat, Curb Parking, Driveway, Garage Door Opener, Golf Cart Parking, Ground Level, Guest, On Street, Oversized, Parking Pad, RV Parking
Patio And Porch Features
Covered, Enclosed, Front Porch, Patio, Rear Porch
Roof
Tile
Window Features
Aluminum Frames, Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Thermal Windows
Financial
Tax Year
2025
Taxes
$3,688
Map
Community
- Address2540 WINNERS CIRCLE KISSIMMEE FL
- SubdivisionWINNERS PARK
- CityKISSIMMEE
- CountyOsceola
- Zip Code34744
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Current real estate data for Single Family in KISSIMMEE as of Aug 29, 2026
2,314
Single Family Listed
161
Avg DOM
217
Avg $ / SqFt
$472,744
Avg List Price
Property Summary
- Located in the WINNERS PARK subdivision, 2540 WINNERS CIRCLE KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34744. It is listed for $650,000 and features 4 beds, 5 baths, and has approximately 3,246 square feet of living space, and was originally constructed in 2000. The current price per square foot is $200. The average price per square foot for Single Family listings in KISSIMMEE is $217. The average listing price for Single Family in KISSIMMEE is $472,744. To schedule a showing of MLS#o6382446 at 2540 WINNERS CIRCLE in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
Similar Listings Nearby
Courtesy of WEMERT GROUP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2540 WINNERS CIRCLE
KISSIMMEE, FL
