2507 WINNERS CIRCLE, KISSIMMEE, FL, 34744
Active103 days on marketListed Apr 12, 2026MLS #S5147254
About this home
2507 WINNERS CIRCLE
Now listed below recently appraised value and recent inspection completed! 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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,914
Sqft
2.51 ac
Lot size
2
Garage
1999
Year built
One
Levels
$285
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,816 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,816/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+36.9%
$/sqft vs Kissimmee actives
$285 vs $212
Days on market
103 vs 45 typical
Where $285/sqft sits among the 400 Kissimmee actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Bluegrass Estates
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Kissimmee. See the full Kissimmee guide →
Bluegrass Estates — neighborhood snapshot
Population
1,645
Median age
38
Median income
$91,875
Median home value
$380,400
Avg household
3
Households w/ children
221
For the school run
Osceola County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Kissimmee market
$369K → $358K
Kissimmee median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
161 of 400
Kissimmee actives have cut their price
Median sold price, Kissimmee, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 41% above the KISSIMMEE 34744 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 2507 WINNERS CIRCLE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$437,500
2521 WINNERS CIRCLE · same community
3 bd · 2 ba · 1,380 sqft · $317/sqft · 6 DOM
Sold · Aug ’25$399,999
2556 BROOKSTONE DRIVE
4 bd · 2 ba · 1,916 sqft · $209/sqft · 108 DOM
Sold · Jul ’25$300,000
2564 BROOKSTONE DRIVE
4 bd · 2 ba · 1,928 sqft · $156/sqft · 39 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2507 WINNERS CIRCLE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2507 WINNERS CIRCLE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
2507 WINNERS CIRCLE FAQs
What would the monthly payment be for 2507 WINNERS CIRCLE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,816/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 2507 WINNERS CIRCLE?+
The most recent tax bill on record (2025) was $2,483. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 2507 WINNERS CIRCLE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Kissimmee?+
At $545,000, this home is listed about 43% above the Kissimmee median of $379,850. The market section on this page shows how the area is trending.
Which schools are assigned to 2507 WINNERS CIRCLE?+
Gateway High School (high), Neptune Middle School (middle), East Lake Elementary School (elementary) — Osceola County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$545,000 runs 41% above the KISSIMMEE 34744 median.
02Time on market is leverage
103 days on market against a Kissimmee median of 45 — sellers in this position are usually ready to negotiate.
03The price has already moved
Listed at $549,000, now $545,000 — a $4K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY AT THE LAKES · Ashley Hellesvig. MLS #S5147254.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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