2521 WINNERS CIRCLE Kissimmee, FL $ 429,999
2521 WINNERS CIRCLE
$ 429,999
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2521 WINNERS CIRCLE

Kissimmee, FL, 34744
$ 429,999
Bedrooms3 Baths2.0 Sq 1,380

Monthly Estimate*

$ 2,648

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Single Family Home for sale in Kissimmee, FL

for $429,999 with 3 bedrooms and 2 full baths. This 1,380 square foot home was built in 2006 on a lot size of 0.75.

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.

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Single Family Active

Price

$ 429,999

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 2,220

Style

Traditional

Lot Size

0.75

Year Built

2006

Town/City

Kissimmee

County/Region

Osceola

MLS | Web ID

O6387060

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air
Utilities Cable Available Electricity Available
Roof Shingle
Appliances Cooktop Microwave Refrigerator
Zoning OR1C
Garage Spaces 2
Architectural Style Traditional
Construction Materials Block
Year Built 2006
View Trees/Woods
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Osceola
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name D S ESTATES
Facing Direction West
Garage Y/N true
Total Rooms 5
Full Baths 2
Status Active
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
City KISSIMMEE
Senior Community Y/N false
MLS Area 34744 - Kissimmee
Lot Size Units Square Feet
Lot Size Square Feet 32626
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Land Lease Y/N false
Tax Annual Amount 2220
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6387060
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 3
Legal Description DS ESTATES PB 10 PG 184 LOT 3
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Kitchen/Family Room Combo Open Floorplan Other
Flooring Laminate
Furnished Y/N Unfurnished
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features In Garage
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Dog Run Other
Vegetation Mature Landscaping Trees/Landscaped Wooded
Fencing Board
Lot Features City Lot Landscaped Oversized Lot
Water Source Public
Lot Size Area 32626
Foundation Details Block
Building Area Total 1962
Lot Size Acres 0.75
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Preferred Real Estate Brokers

Broker

hilton@orlandoreinvesting.com

Email

Affordability Calculator

$2,833
Per Month
93%
7%
0%
Monthly Principal & Interest
$2,648
Monthly Property Taxes
$185
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
3/5/2026$429,999 Listed Price

Map


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2521 WINNERS CIRCLE, Kissimmee, FL, 34744 is a Single Family Home for sale at $429,999 with 1,380 sqft and a lot size of 0.75. 2521 WINNERS CIRCLE has 3 bedrooms, 2.0 baths, and was built in 2006. The property's zip code is 34744 which is in Kissimmee, FL