Winners Park
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, the MLS records 1 closed sale in Winners Park in Kissimmee, FL, the most recent in October 2026. Across Kissimmee as a whole, 4,246 homes closed in the last 12 months at a median of $360,000, 64 median days on market, with 2,907 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,480 ($4,880 with the full homestead exemption).
Price here is driven by the house, not the address. With just 15 homes spanning a build range from 1993 to 2024 and a median living area north of 4,400 square feet, Winners Park is a small pocket of larger homes where condition, age, and finish level set value more than any community premium. Expect a wide spread between the oldest and newest homes, and read each listing on its own merits.
Right now there are no active listings. That means no current comps to anchor a price, so both sides are working from recent closings and the specifics of a given home rather than a live market. For a seller, thin inventory can work in your favor when a well-prepared home comes up. For a buyer, patience and a readiness to move when something lists both matter.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Winners Park right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winners Park is a small enclave of 15 larger homes in Kissimmee, where the median build year of 2001 sits inside a range that reaches from the early 1990s to brand-new construction. The size of the homes here is the headline.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Winners Park is best for.
Best for
- Buying for substantial living space in a small enclave
- Trading up from a smaller home and wanting room to spread out
- Buyers who prefer an owner-occupied block over a rental-heavy one
Probably not for
- Needing a shared pool, clubhouse, or other community amenities
- Wanting a fast purchase from a deep pool of active listings
- Seeking a smaller, lower-maintenance footprint
The market around Winners Park
Winners Park is a small community — 33 recorded sales on file, most recently in 2019 — too few for its own price trend. Here is the market around it.
Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).
Homes here are single family residence.
In ZIP 34744 (Kissimmee), 271 homes closed in the last 12 months at a median of $390K ($212/sq ft), up 5.3% year over year, with a median 36 days on market. See the live ZIP 34744 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Winners Park specifically. Momentum Research analysis of MLS records.
The Winners Park buying strategy.
If we were buying in Winners Park today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Winners Park.
A small, large-home pocket
The defining trait is scale: a median living area above 4,400 square feet puts most of these homes well into move-up territory. With only 15 homes total and a build range spanning three decades, no two will be alike - some will reflect early-2000s construction, others recent builds, and pricing will track those differences closely.
About 60 percent of homes here are homesteaded, which points to a core of owner-occupants rather than a rental-heavy block. No community amenities turn up in current MLS listings, so this is land and square footage rather than a shared-facility lifestyle. That suits buyers who want room over a managed amenity package.
The location and the amenities are priced into every listing in Winners Park. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 15-home enclave with nothing currently active, the data is thin and the right read comes from knowing each home's history, not a dashboard. We track what actually closes here, help sellers prepare for a market with few comps to lean on, and keep buyers ready to act the moment something lists.
Winners Park in 15 seconds.
Tools for a Winners Park buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winners Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winners Park, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winners Park home worth?
Get a no-obligation home value based on real comparable sales in Winners Park, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Kissimmee →
Recently off market in Winners Park
Homes in Winners Park that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 2540 Winners Circle · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 34 (FL DOR 2025 assessment roll) |
| Years built | 1979–2024 (median 1999.5) |
| Typical living area | 3,408 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 91% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2026 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winners Park key facts,” movewithmomentum.com/neighborhoods/winners-park-kissimmee, data as of November 13, 2026.
Housing distress & ownership in Winners Park, Kissimmee
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
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Kissimmee guides & data
- Market data
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- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
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- Florida flood insurance calculator
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Email me new listings in Winners Park
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Winners Park
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Winners Park will answer, and the answer is published on this page for the next buyer.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
How many homes are in Winners Park?
What share of Winners Park is owner-occupied?
When were the homes in Winners Park built?
Who is the best real estate agent for Winners Park?
How do I find a top Kissimmee real estate agent who knows Winners Park?
Can Momentum Realty connect me with an agent for Winners Park?
Where is Winners Park, and what county is it in?
Should you buy in Winners Park?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 26, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. A Momentum agent can price yours against live local comps.
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See how Winners Park fits the bigger picture — live prices, inventory, and Momentum Scores: