2540 WINNERS CIRCLE KISSIMMEE, FL 34744

$725,000

4 Beds

4.5 Baths

3246 sqft

Property Details

MLS#

O6382446

Type

Single Family Residence

Status

Active Listing

Square Footage

3,246

Bedrooms

4

Bathrooms

4 full | 1 half

Year Built

2000

Tax Amount

$3,688

Garage Spaces

4

Property Description

One or more photo(s) has been 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**

Amenities

Cooling:Central Air

Hurricane Shutters

Lighting

Private Mailbox

Rain Gutters

Sliding Doors

Storage

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

Payment Calculator

per month

 Principal & Interest

 Property Tax

 Mortage Insurance

 HOA

 Home Owners Insurance

Home Price
Interest Rate
Down Payment
 Customize Calculations
Property Taxes
/ year
Homeowner's Insurance
/ month
HOA Dues
Mortgage Insurance
Loan Type
Location Map

The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

All listings featuring the BMLS logo are provided by Beaches MLS Inc. Copyright 2026 Beaches MLS. This information is not verified for authenticity or accuracy and is not guaranteed.

© 2026 Beaches Multiple Listing Service, Inc. All rights reserved.

The data relating to real estate for sale on this web site comes in part from the participating Associations/MLS's Miami Association of Realtors, and the Realtor Association of Greater Ft. Lauderdale.

Information is deemed reliable but not guaranteed. Copyright 2026, Miami Association of Realtors, Realtor Association of Greater Ft. Lauderdale, and the South Broward Board of Realtors. All rights reserved. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited.

Some properties that appear for sale on this limited electronic display may no longer be available. For the most current information, contact one of our agents.