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.
Sold for $437,500
$437,500
2521 Winners Cir, Kissimmee, FL 34744
3beds
1,380sqft
Single Family Residence
Built in 2006
0.75 Acres Lot
$432,200 Zestimate®
$317/sqft
$2,300 Estimated rent
Home value
$432,200
$393,000 - $475,000
$2,300/mo
Zestimate® history
Owner options
List your home for rent
$2,300/mo
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$2,300/mo
Rent Zestimate®
Refinance and save
$2,882/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$2,882/mo
Est. payment
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List your homeWhat's special
Zillow last checked:
Listing updated:
Listed by:
Justin Hilton 407-473-0869,
PREFERRED REAL ESTATE BROKERS 407-440-4900
Bought with:
Sonia Crespo Ballesteros, 3331645
LPT REALTY, LLC
Source: Stellar MLS,MLS#: O6387060
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Storage Closet
- Level: First
- Area: 165 Square Feet
- Dimensions: 15x11
Bedroom 1
- Features: Storage Closet
- Level: First
- Area: 90 Square Feet
- Dimensions: 9x10
Bedroom 2
- Features: Storage Closet
- Level: First
- Area: 120 Square Feet
- Dimensions: 10x12
Kitchen
- Level: First
- Area: 264 Square Feet
- Dimensions: 22x12
Living room
- Level: First
- Area: 288 Square Feet
- Dimensions: 18x16
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Cooktop, Microwave, Refrigerator
- Laundry: In Garage
Features
- Kitchen/Family Room Combo, Open Floorplan, Other
- Flooring: Laminate
- Has fireplace: No
Interior area
- Total structure area: 1,962
- Total interior livable area: 1,380 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: One
- Stories: 1
- Exterior features: Dog Run, Other
- Fencing: Board
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 0.75 Acres
- Features: City Lot, Landscaped, Oversized Lot
- Residential vegetation: Mature Landscaping, Trees/Landscaped, Wooded
Details
- Parcel number: 172530292100010030
- Zoning: OR1C
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Block
- Roof: Shingle
Condition
- New construction: No
- Year built: 2006
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available, Electricity Available
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: D S ESTATES
HOA
- Has HOA: No
Location
- Region: Kissimmee
Financial & listing details
- Price per square foot: $317/sqft
- Tax assessed value: $209,600
- Annual tax amount: $2,220
- Date on market: 3/5/2026
- Cumulative days on market: 6 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 4/7/2026 | Sold | $437,500+1.7%$317/sqft |
Source:  Stellar MLS #O6387060 Report a problem | ||
| 3/11/2026 | Pending sale | $429,999$312/sqft |
Source: Stellar MLS #O6387060 Report a problem | ||
| 3/6/2026 | Listed for sale | $429,999+2050%$312/sqft |
Source: Stellar MLS #O6387060 Report a problem | ||
| 3/2/1999 | Sold | $20,000$14/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,220 +6.6% | $209,600 +0.1% |
| 2024 | $2,082 +2.4% | $209,300 +1.7% |
| 2023 | $2,033 +5.3% | $205,800 +21.2% |
| 2022 | $1,932 +1.3% | $169,800 +8.6% |
| 2021 | $1,907 +2.5% | $156,300 +3.3% |
| 2020 | $1,861 +2.1% | $151,300 +6.3% |
| 2019 | $1,823 | $142,300 +13% |
| 2018 | $1,823 +5.5% | $125,935 +2.1% |
| 2017 | $1,728 +0.5% | $123,345 +2.1% |
| 2016 | $1,720 +1.7% | $120,809 +0.7% |
| 2015 | $1,692 +1.6% | $119,970 +0.8% |
| 2014 | $1,664 | $119,018 +1.5% |
| 2013 | -- | $117,260 +1.7% |
| 2012 | -- | $115,300 |
Find assessor info on the county website
Neighborhood: 34744
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Nearby schools
GreatSchools rating
- 4/10East Lake Elementary SchoolGrades: PK-5Distance: 4.2 mi
- 7/10Neptune Middle SchoolGrades: 6-8Distance: 3.5 mi
- 5/10Tohopekaliga High SchoolGrades: PK,9-12Distance: 3.5 mi
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Estimated market value
$432,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$432,200
- Florida
- Osceola County
- Kissimmee
- 34744
- 2521 Winners Cir
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