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$800,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,246 Sq. Ft.
  • Updated 6 hours ago
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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**

Full Property Details for 2540 Winners Cir

General

  • Price: $800,000
  • Taxes: $3,688 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6382446
  • Updated: 2/19/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 12
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Surface Counters, Stone Counters, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Filtration System, Water Softener
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Garage

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Auto Cleaner, Gunite, In Ground, Lighting, Screen Enclosure

Exterior

  • Exterior Features: Hurricane Shutters, Lighting, Private Mailbox, Rain Gutters, Sliding Doors, Storage
  • Deck/Patio: Covered, Enclosed, Front Porch, Patio, Rear Porch
  • Porch/Patio/Deck: Covered, Enclosed, Front Porch, Patio, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Covered Spaces: 4
  • Parking Features: Boat, Curb Parking, Driveway, Garage Door Opener, Golf Cart Parking, Ground Level, Guest, On Street, Oversized, Parking Pad, RV Parking

Location

  • Area: 34744 - Kissimmee
  • County: Osceola
  • Development Name: 34744 - Kissimmee
  • Subdivision: WINNERS PARK
  • Driving Directions: From 527A/Boggy Creek Rd, Turn right onto Simpson Rd, Turn left onto Winners Cir. Home will be on the right.
  • Direction Faces: North

School Information

  • Elementary School: East Lake Elem
  • Middle School: Neptune Middle (6-8)
  • High School: Tohopekaliga High School

Community

  • Community Name: 34744 - Kissimmee
  • Pet Restrictions: Buyer to verify pet restrictions with city/county

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fiber Optics, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Windows: Aluminum Frames, Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Thermal Windows
  • Stories/Levels: Two
  • Square Feet: 3,246
  • Sq. Ft. Source: Public Records
  • Year Built: 2000

Additional Structures

  • Other Structures: Other, Shed(s), Workshop

Lot Features

  • Lot Size (Acres): 0.5
  • Lot Size (Sq. Ft.): 21,824
  • Lot Size: 21824
  • Frontage: Street Dead-End, Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $3,688
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINNERS PARK PB 7 PG 48 LOT 6
  • Flood Zone Info: X
  • APN: 172530551500010060
  • Property ID: 172530551500010060
  • Block/Lot/Section: 1

Listed by Wemert Group Realty Llc

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Listing agents

— 2540 Winners Cir —

  • Wemert Group Realty Llc

  • Wemert Group Realty Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2540 Winners Cir

School District:Osceola County School District
NameGradesDistance
Tohopekaliga High School
3675 Boggy Creek Road, Kissimmee, FL 34744
9-123.4 mi
East Lake Elementary School, Kissimmee, FL
4001 Boggy Creek Road, Kissimmee, FL 34744
PK-54.1 mi
Neptune Middle School
2727 Neptune Road, Kissimmee, FL 34744
6-83.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2540 Winners Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/19/2026
Listed
$800,000
308.16%
MLS
5/01/2003
Sold
$196,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2540 Winners Cir

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,688
5%
$228,639
3%
2024
$3,503
2%
$222,196
3%
2023
$3,422
4%
$215,725
3%
2022
$3,277
1%
$209,442
3%
2021
$3,239
-34%
$203,342
-25%
2020
$4,922
33%
$269,900
8%
2019
$3,710
3%
$249,201
2%
2018
$3,598
-2%
$244,555
2%
2017
$3,672
1%
$239,525
2%
2016
$3,632
8%
$234,599
1%
2015
$3,353
-7%
$232,969
1%
2014
$3,617
1%
$231,121
1%
2013
$3,580
—
$227,706
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Wemert Group Realty Llc

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2540 Winners Circle, Kissimmee, FL 34744 (MLS# O6382446) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 2540 Winners Circle is currently listed for $800,000 and was received on February 19, 2026. Want to learn more about 2540 Winners Circle? Do you have questions about finding other Single Family real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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