$545,000
2507 Winners Circle
Kissimmee, FL 34744
Listing updated: June 13, 2026 at 9:30 AM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Now listed below recently appraised value! Available again, buyer financing fell through. Welcome home to 2.5 acres of private Florida living! This charming 3-bedroom, 2-bathroom block home in Kissimmee offers the rare combination of expansive acreage and ultimate convenience, all with NO HOA. Located just moments from Osceola Heritage Park and offering quick access to major thoroughfares, this property is perfectly situated for easy commuting and entertainment. The original owners have meticulously maintained and updated the residence, ensuring move-in readiness. Significant recent improvements include a NEW ROOF in 2018, a NEW 4 TON HVAC SYSTEM with a Ditek Surge Protector installed in 2022, NEW Water Heater 2026, an exterior repaint in 2025, and a new septic pump and service in early 2026. Additionally, enjoy the freshly rescreened porch and new vinyl privacy fencing. The home was also built with Pest Tubes in the walls and filled quarterly. Step inside to find vaulted ceilings and three skylights illuminating the open living areas, which feature a formal living room with a bay window and a cozy family room complete with a wood-burning fireplace. The primary suite offers a private retreat with a double pocket sliding glass door leading to the lanai, and a spacious bath featuring a double vanity, walk-in shower, and soaker tub. The home features a mix of laminate in the bedrooms and living/dining areas and tile in the kitchen and baths for ease of maintenance. Enjoy the tranquil Florida outdoors from the screened lanai, complete with new fans and a durable Chattanooga Rock floor, which provides scenic views of trees and wilderness on your 2.5-acre lot. The back of the home features an extended paver patio perfect for outdoor entertaining. Additionally, if a pool is in your future plans, the second guest bath includes a convenient door leading directly to the patio.
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 history31 days on market
- Status: ActiveMay 19, 2026
- Listed$549,000Apr 12, 2026
- Price reduced$545,000
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 31
- Subdivision
- D S Estates
- County
- Osceola
- Year built
- 1999
- Living area
- 1,914 sq ft
- Price/sq ft
- $285
- Building area
- 2,777 sq ft (Public Records)
- Lot size
- 109,466 sq ft
- Lot category
- 2 to less than 5
- Flood zone
- X (12097C0090G)
- Garage
- 2 spaces
- Annual taxes
- $2,483 (2025)
- Parcel #
- 17-25-30-2921-0001-0010
- Zoning
- OR1C
- MLS #
- S5147254
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Flooring
- Laminate, Tile
- Appliances
- Dryer, Microwave, Range, Refrigerator, Washer
- Interior features
- Ceiling Fans(s)
- Laundry
- Laundry Room
- Stories / Levels
- One
- Direction faces
- Southwest
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
HOA & Financial
- Total monthly fees
- $0/mo
- Total annual fees
- $0
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1-7 Days
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- ***PLEASE VERIFY ALL COUNTY AND MUNICIPAL ORDINANCES***
- Approval process
- ***PLEASE VERIFY ALL COUNTY AND MUNICIPAL ORDINANCES***
Exterior & Construction
- Exterior features
- Rain Gutters
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, 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 | |
| Primary Bedroom | First | |
| Living Room | First |
Listing Details
- Listing date
- 2026-04-05
- On market date
- 2026-04-12
- Original list price
- $549,000
- Occupant type
- Owner
- MLS area
- 34744 - Kissimmee
- Listing AOR
- Osceola
- Status changed
- 2026-05-19
- Tax legal description
- DS ESTATES PB 10 PG 184 LOT 1
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 Osceola Pkwy E: Turn right onto Osceola Pkwy- Turn right onto Co Rd 527/Old Dixie Hwy- Turn left onto Garden St- Turn right onto Michigan Ave- Turn left onto Mill Slough Rd- Turn right onto Denn John Ln- Turn left onto Old Boggy Creek Rd- Turn left onto Fortune Rd- Use the middle lane to turn left onto Simpson Rd- Continue on Winners Cir to your destination- Turn right onto Winners Cir- Turn left- Destination is on your left
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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 13, 2026 at 9:30 AM 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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