Winners Park
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in KISSIMMEE, FL · median $373,400 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Winners Park is a community in Kissimmee, Osceola County, FL. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
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.
ZIP and county figures describe the wider market, not Winners Park specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Winners Park
Live MLS inventory for Winners Park. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Winners Park listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period %s through %s. Tap any home to ask about it.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- East Lake Elem · Elementary
- Neptune Middle (6-8) · Middle
- Tohopekaliga High School · High
Zoned schools reflect the assignments reported on recent Winners Park listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winners Park address.
Shop the zone: Homes zoned for Tohopekaliga High School
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 closer look at the Winners Park market
The housing stock is 15 homes built between 1993 and 2024, and 60% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
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 →
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.
WINNERS PARK Market Scorecard
WINNERS PARK is currently a thin data market. Limited supply, a median asking price of n/a.
Typical home value in the 34744 ZIP is $385,786, about 10.6% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Winners Park fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Winners Park with Momentum Realty’s local guides.