Front - 2507 WINNERS CIR, KISSIMMEE
Estimated Lot Outline - 2507 WINNERS CIR, KISSIMMEE
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Formal Living - 2507 WINNERS CIR, KISSIMMEE
Formal Living - 2507 WINNERS CIR, KISSIMMEE
Formal Living - 2507 WINNERS CIR, KISSIMMEE
Primary Bedroom - 2507 WINNERS CIR, KISSIMMEE
Primary Bedroom - 2507 WINNERS CIR, KISSIMMEE
Primary Bathroom - 2507 WINNERS CIR, KISSIMMEE
Primary Bathroom - 2507 WINNERS CIR, KISSIMMEE
Primary Bathroom - 2507 WINNERS CIR, KISSIMMEE
Primary Bathroom/Closet - 2507 WINNERS CIR, KISSIMMEE
Primary Bedroom - 2507 WINNERS CIR, KISSIMMEE
Dining Room - 2507 WINNERS CIR, KISSIMMEE
Dining Room - 2507 WINNERS CIR, KISSIMMEE
Dining Room - 2507 WINNERS CIR, KISSIMMEE
Kitchen - 2507 WINNERS CIR, KISSIMMEE
Kitchen - 2507 WINNERS CIR, KISSIMMEE
Kitchen - 2507 WINNERS CIR, KISSIMMEE
Kitchen - 2507 WINNERS CIR, KISSIMMEE
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$538,000

2507 WINNERS CIR
KISSIMMEE, FL 34744
Listed by Ashley Hellesvig · KELLER WILLIAMS REALTY AT THE LAKES
Bedrooms
3
Bathrooms
2
Living area
1,914 sqft
Year built
1999

About this home

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.

Highlights

Fireplace

Property details

MLS
Stellar MLS
MLS #
MFRS5147254
Property type
Single Family Residence
Subdivision
D S ESTATES
Status
Active
Days on market
85
On market date
April 12, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
2
Parking spaces
N/A
Lot size
2.51 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
CYPRESS ELEMENTARY SCHOOL
0.59 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
495
Student:teacher ratio
14.1:1
District
OSCEOLA
MiddleCharter
SPORTS LEADERSHIP ARTS MANAGEMENT (SLAM)
1.52 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
139
Student:teacher ratio
17.4:1
District
OSCEOLA
High
OSCEOLA TECHNICAL COLLEGE KISSIMMEE CAMPUS
0.89 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
0
Student:teacher ratio
0.0:1
District
OSCEOLA

Walkability

Blended score for KISSIMMEE's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

25
Car-dependent
out of 100
EPA National Walkability Index
7.3 / 20 -- Below average walkable
Google Places amenity density
8 / 100
Restaurants & cafes1
Grocery stores0
Parks1
Schools0
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in KISSIMMEE, from live MLS data.

On the market 85 days -- 16 fewer days than KISSIMMEE's current average of 101 days.
For reference, the median list price across 5,299 active listings in KISSIMMEE right now is $314,990.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Adjust tax / insurance estimates
% / yr
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/mo
Est. monthly payment
$3,390/mo
$107,600 down
$430,400 loan
Principal & interest$2,792
Property tax (est.)$448
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 13 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.