Now listed below recently appraised value and recent inspection completed! Back on market, no fault of seller, 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.
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.
Property Details
Price:
$538,000
MLS #:
S5147254
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
D S ESTATES
Neighborhood:
34744kissimmee
Listed Date:
Apr 12, 2026
Finished Sq Ft:
1,914
Total Sq Ft:
2,777
Lot Size:
109,466 sqft / 2.51 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
East Lake Elem
Middle School:
Neptune Middle (6-8)
High School:
Tohopekaliga High School
Interior
Appliances
Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Laminate, Tile
Heating
Central
Interior Features
Ceiling Fan(s)
Laundry Features
Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Southwest
Exterior Features
Rain Gutters
Garage Spaces
2
Roof
Shingle
Financial
Tax Year
2025
Taxes
$2,483
Map
Community
- Address2507 WINNERS CIRCLE KISSIMMEE FL
- SubdivisionD S ESTATES
- CityKISSIMMEE
- CountyOsceola
- Zip Code34744
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Current real estate data for Single Family in KISSIMMEE as of Oct 19, 2026
2,257
Single Family Listed
166
Avg DOM
215
Avg $ / SqFt
$474,640
Avg List Price
Property Summary
- Located in the D S ESTATES subdivision, 2507 WINNERS CIRCLE KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34744. It is listed for $538,000 and features 3 beds, 2 baths, and has approximately 1,914 square feet of living space, and was originally constructed in 1999. The current price per square foot is $281. The average price per square foot for Single Family listings in KISSIMMEE is $215. The average listing price for Single Family in KISSIMMEE is $474,640. To schedule a showing of MLS#s5147254 at 2507 WINNERS CIRCLE in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLER WILLIAMS REALTY AT THE LAKES. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2507 WINNERS CIRCLE
KISSIMMEE, FL

