Date
Details
Price
Change
Source
3/05/2026
Listed
$429,999
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
Welcome to 2521 Winners Circle in Kissimmee, a beautifully fully renovated 3-bedroom, 2-bathroom home that perfectly blends privacy, convenience, and opportunity. Situated on an oversized lot, this property offers a rare chance to create something truly special - with the option to acquire two additional contiguous parcels, giving you the space to build the ultimate family compound or expanded investment portfolio. Inside, the home shines with brand-new flooring and a new roof, delivering both modern style and peace of mind for years to come. The thoughtfully updated interior creates a clean, welcoming feel throughout, while the included appliances convey with the sale, making this a true turn-key opportunity for homeowners and investors alike. The location is simply premiere. With quick access to major highways, getting anywhere for a road trip, family outing, or daily commute is effortless. Whether you're heading to Orlando, the coast, or anywhere Central Florida has to offer, you're perfectly positioned. Enjoy being just a short drive from world-famous theme parks, exciting sporting events, and the renowned rodeos and events hosted by KVLS, giving you year-round entertainment and lifestyle opportunities. For residential investors, this property checks every box - fully renovated, turn-key, and ready to generate cash flow from day one. With privacy, expansion potential, and unbeatable access to Central Florida's best attractions, 2521 Winners Circle is a rare offering you won't want to miss. Schedule your showing today - opportunities like this don't last long.
Full Property Details
Full Property Details for 2521 Winners Cir
General
- Price: $429,999
- Taxes: $2,220 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6387060
- Updated: 3/5/2026
- Added to Site: 5 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 5
- Interior Features: Kitchen and Family Room Combination, Open Floorplan, Other
- Appliances: Cooktop, Microwave, Refrigerator
- Furnishings: Unfurnished
- Flooring: Laminate
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: In Garage
Exterior
- Exterior Features: Dog Run, Other
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34744 - Kissimmee
- County: Osceola
- Development Name: 34744 - Kissimmee
- Subdivision: D S ESTATES
- Driving Directions: FROM TURNPIKE TAKE EXIT FOR LANDSTAR THEN TURN RIGHT ONTO LANDSTAR THEN TURN RIGHT ONTO SIMPSON RD THEN LEFT ONTO WINNERS AND DRIVE TO 2521
- Direction Faces: West
Community
- Community Name: 34744 - Kissimmee
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: Cable TV Available, Electricity Available
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 1,380
- Sq. Ft. Source: Public Records
- Year Built: 2006
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.75
- Lot Size (Sq. Ft.): 32,626
- Lot Size: 32626
- Street/Road Desc.: Paved
- Fencing (Description): Board
Financial Considerations
- Tax Amount: $2,220
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: DS ESTATES PB 10 PG 184 LOT 3
- Flood Zone Info: X
- APN: 172530292100010030
- Property ID: 172530292100010030
- Block/Lot/Section: 1
Listed by Preferred Real Estate Brokers
We Value Your Privacy
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Listing agent
— 2521 Winners Cir —
Preferred Real Estate Brokers
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 2521 Winners Cir
School District:Osceola County School District
| Name | Grades | Distance |
|---|---|---|
Tohopekaliga High School 3675 Boggy Creek Road, Kissimmee, FL 34744 | 9-12 | 3.4 mi |
East Lake Elementary School, Kissimmee, FL 4001 Boggy Creek Road, Kissimmee, FL 34744 | PK-5 | 4.1 mi |
Neptune Middle School 2727 Neptune Road, Kissimmee, FL 34744 | 6-8 | 3.5 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 2521 Winners Cir
Tax History
Tax History for 2521 Winners Cir
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,220
7%
$149,675
3%
2024
$2,082
2%
$145,457
3%
2023
$2,033
7%
$141,221
6%
2021
$1,907
-1%
$133,115
-3%
2022
$1,932
1%
$137,108
4%
2021
$1,907
10%
$131,278
4%
2018
$1,728
-5%
$125,935
-2%
2019
$1,823
6%
$128,327
4%
2017
$1,720
2%
$123,345
2%
2016
$1,692
-1%
$120,809
1%
2015
$1,707
3%
$119,970
1%
2014
$1,664
2%
$119,018
1%
2013
$1,638
—
$117,260
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 2521 Winners Cir
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- Lots/Land
- Active
- Updated 4 days ago
- 0.22Acres
Listed by Keller Williams Legacy Realty
- Single Family
- Active
- Updated 3 days ago
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Listed by Mary Heidrich (407) 493-5336
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Listed by David Plasencia, Esq. (407) 579-9369
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- Active
- Updated 4 days ago
- 4Beds
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- 1,757Sq. Ft.
Listed by Bridget Snodgrass (386) 804-0684
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- Single Family
- Active
- Updated 6 days ago
- 3Beds
- 2Total Baths
- 1,972Sq. Ft.
Listed by Royalty R E Boutique Inc
- Single Family
- Active
- Updated 11 hours ago
- 2Beds
- 1Total Bath
- 1,005Sq. Ft.
Listed by Keller Williams Advantage Iii
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Listed by M & N Holloway
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- Updated 5 days ago
- 5Beds
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- 2,447Sq. Ft.
Listed by Dr Horton Realty Of Central Florida Llc
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- Single Family
- Closed
- 3Beds
- 3Total Baths
- 1,920Sq. Ft.
Listed by Fusilier Management Group
Sold by Odry Vargas Realty Group
Sold by Odry Vargas Realty Group
- Single Family
- Closed
- 5Beds
- 4Total Baths
- 2,083Sq. Ft.
Listed by Wra Business & Real Estate
Sold by Stellar Non-Member Office
Sold by Stellar Non-Member Office
- Single Family
- Closed
- 4Beds
- 2Total Baths
- 1,844Sq. Ft.
Listed by Stellar Non-Member Office
Sold by La Rosa Realty Llc
Sold by La Rosa Realty Llc
- Single Family
- Closed
- 4Beds
- 3Total Baths
- 1,967Sq. Ft.
Listed by Magnus Realty Group Llc
Sold by Magnus Realty Group Llc
Sold by Magnus Realty Group Llc
2521 Winners Circle, Kissimmee, FL 34744 (MLS# O6387060) is a Single Family property with 3 bedrooms and 2 full bathrooms. 2521 Winners Circle is currently listed for $429,999 and was received on March 05, 2026. Want to learn more about 2521 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.