2540 WINNERS CIRCLE KISSIMMEE FL 34744 MLS #O6382446

2540 WINNERS CIRCLE
KISSIMMEE, FL, 34744
$739,000
4 Beds
4.5 Baths
3,246 SqFt
0.5 Acres
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MLS #O6382446 image #0
Open House Apr 26, 2026
11:00 – 03:00
**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:
$739,000
MLS #:
O6382446
Status:
Active
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
Pool34744 – Kissimmee34744kissimmeeWinners ParkEast Lake ElemNeptune Middle (6-8)Tohopekaliga High SchoolBuyer To Verify Leasing Restrictions With City/countyNo MinimumPets Allowed

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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

Subdivisions in KISSIMMEE

Market Summary

Current real estate data for Single Family in KISSIMMEE as of Apr 24, 2026
2,395
Single Family Listed
156
Avg DOM
220
Avg $ / SqFt
$478,022
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 $739,000 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 $228. The average price per square foot for Single Family listings in KISSIMMEE is $220. The average listing price for Single Family in KISSIMMEE is $478,022. To schedule a showing of MLS#o6382446 at 2540 WINNERS CIRCLE in KISSIMMEE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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2540 WINNERS CIRCLE
KISSIMMEE, FL