$699,000
2540 Winners Circle
Kissimmee, FL 34744
Listing updated: June 6, 2026 at 3:06 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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**
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history107 days on market
- Status: ActiveFeb 19, 2026
- Listed$800,000Feb 19, 2026
- Price reduced$699,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 107
- Subdivision
- Winners Park
- County
- Osceola
- Year built
- 2000
- Living area
- 3,246 sq ft
- Price/sq ft
- $215
- Building area
- 3,710 sq ft (Public Records)
- Lot size
- 21,824 sq ft
- Lot category
- 1/2 to less than 1
- Flood zone
- X (12097C0090G)
- Garage
- 4 spaces
- Pool
- Private pool
- Annual taxes
- $3,688 (2025)
- Parcel #
- 17-25-30-5515-0001-0060
- Zoning
- OR1C
- MLS #
- O6382446
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Interior Details
- Bedrooms
- 4
- Full bathrooms
- 4
- Half bathrooms
- 1
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Filtration System, Water Softener
- Interior features
- 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
- Laundry
- In Garage
- Stories / Levels
- Two
- Direction faces
- North
- In-law suite
- Yes
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 4
- Attached garage
- Yes
- Parking features
- Boat, Curb Parking, Driveway, Garage Door Opener, Golf Cart Parking, Ground Level, Guest, On Street, Oversized, Parking Pad, RV Access/Parking
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Buyer to verify leasing restrictions with city/county
- Approval process
- Buyer to verify any approval process with city/county
Exterior & Construction
- Exterior features
- Hurricane Shutters, Lighting, Private Mailbox, Rain Gutters, Sliding Doors, Storage
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 22x12 |
| Dining Room | First | 12x12 |
| Living Room | First | 12x12 |
| Family Room | First | 17x13 |
| Primary Bedroom | Second | 14x13 |
| Primary Bathroom | Second | 13x9 |
| Bedroom 2 | Second | 14x11 |
| Bedroom 3 | Second | 12x11 |
| Loft | Second | |
| Living Room | First | 16x10 |
| Bedroom 4 | First | 11x10 |
| Kitchen | First | 14x10 |
Listing Details
- Listing date
- 2026-02-19
- On market date
- 2026-02-19
- Original list price
- $800,000
- Occupant type
- Owner
- MLS area
- 34744 - Kissimmee
- Listing AOR
- Orlando Regional
- Status changed
- 2026-02-19
- Tax legal description
- WINNERS PARK PB 7 PG 48 LOT 6
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From 527A/Boggy Creek Rd, Turn right onto Simpson Rd, Turn left onto Winners Cir. Home will be on the right.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 6, 2026 at 3:06 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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