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$565,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,914 Sq. Ft.
  • Updated 6 days ago
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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.

Full Property Details for 2507 Winners Cir

General

  • Price: $565,000
  • Taxes: $2,483 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5147254
  • Updated: 5/21/2026
  • Added to Site: 46 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 3
  • Interior Features: Ceiling Fan(s)
  • Fireplace: Yes
  • Fireplace(s): Wood Burning
  • Appliances: Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Rain Gutters

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 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
  • Direction Faces: Southwest

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: ***PLEASE VERIFY ALL COUNTY AND MUNICIPAL ORDINANCES***

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,914
  • Sq. Ft. Source: Public Records
  • Year Built: 1999

Lot Features

  • Lot Size (Acres): 2.51
  • Lot Size (Sq. Ft.): 109,466
  • Lot Size: 2.513
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $2,483
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: DS ESTATES PB 10 PG 184 LOT 1
  • Flood Zone Info: X
  • APN: 172530292100010010
  • Property ID: 172530292100010010
  • Block/Lot/Section: 1

Listed by Keller Williams Realty At The Lakes

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Listing agent

— 2507 Winners Cir —

  • Keller Williams Realty At The Lakes

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 2507 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
6-83.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2507 Winners Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/18/2026
Price Increased
$565,000
2.91%
MLS
4/12/2026
Listed
$549,000
—
MLS
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 2507 Winners Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$2,337
—
$168,631
3%
2024
$2,337
2%
$163,879
3%
2023
$2,283
5%
$159,106
3%
2022
$2,174
1%
$154,472
3%
2021
$2,150
2%
$149,973
1%
2020
$2,102
7%
$147,903
4%
2018
$1,966
—
$141,883
2%
2017
$1,959
2%
$138,965
2%
2016
$1,929
-6%
$136,107
-6%
2019
$2,063
6%
$144,578
7%
2015
$1,949
2%
$135,161
1%
2014
$1,906
1%
$134,089
1%
2013
$1,879
—
$132,108
—
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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Listed by Keller Williams Realty At The Lakes

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2507 Winners Circle, Kissimmee, FL 34744 (MLS# S5147254) is a Single Family property with 3 bedrooms and 2 full bathrooms. 2507 Winners Circle is currently listed for $565,000 and was received on April 12, 2026. Want to learn more about 2507 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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