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**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**
| DAYS ON MARKET | 1 | LAST UPDATED | 2/19/2026 |
|---|---|---|---|
| TRACT | WINNERS PARK | YEAR BUILT | 2000 |
| COMMUNITY | 34744 - Kissimmee | GARAGE SPACES | 4.0 |
| COUNTY | Osceola | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | East Lake Elem |
|---|---|
| Jr. High School | Neptune Middle (6-8) |
| High School | Tohopekaliga High School |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Softener |
| AREA | 34744 - Kissimmee |
| CONSTRUCTION | Block, Stucco |
| EXTERIOR | Lighting, Rain Gutters, Storage |
| GARAGE | Yes |
| HEAT | Central, Electric |
| INTERIOR | Eat-in Kitchen, Stone Counters, Walk-In Closet(s) |
| LOT | 0.5 acre(s) |
| LOT DESCRIPTION | Cul-de-sac, Landscaped, Paved |
| PARKING | Boat, Driveway, Garage Door Opener, Guest, On Street, Oversized, Parking Pad, RV Access/Parking, Attached |
| POOL | Yes |
| POOL DESCRIPTION | Gunite, In Ground, Screen Enclosure, Private |
| SEWER | Septic Tank |
| STORIES | 2 |
| SUBDIVISION | WINNERS PARK |
| TAXES | 3688 |
| UTILITIES | Cable Available, Electricity Connected, Water Connected |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Jenny Wemert, WEMERT GROUP REALTY LLC, 407-214-3967
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 2/19/26 7:54 PM PST.
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