Does this search cover more than Kissimmee?

Yes. This search follows the full Osceola County boundary, including Kissimmee, St. Cloud and other county communities. It is not limited to Kissimmee or based on an Orlando metro radius. Your under-$500K ceiling applies across that county area, though matching availability varies by location.

Is this search limited to detached houses?

No. The search applies no property-type or bedroom restriction, and it has no minimum asking price. It selects properties within Osceola County advertised below $500,000. Review each result's property classification, layout and ownership responsibilities rather than assuming every match is a detached house or has the same maintenance needs.

Does a CDD assessment replace association dues?

No. A Community Development District funds and maintains community infrastructure and amenities through taxes and assessments. Association dues are separate charges. For a home you are considering, check whether either or both apply, review the parcel's tax statement and association documents, and keep those costs separate in your ownership budget.

Does a nearby public park come with private access?

No. Public lakefront parks provide local recreation, but a nearby address does not establish private lake access, a boat slip or amenities included with the property. Separate the facilities you can visit as a member of the public from any access rights documented for the specific home or community.

Stucco homes with green lawns and palm trees beside a gently curving residential street and sidewalk in warm daylight.

Full-county property search

Osceola County homes for sale under $500K, FL

Compare Osceola County homes for sale under $500K, FL. We help you weigh location, property responsibilities and ongoing costs across the county.

Matching homes for sale in Osceola County

3,538 listings

64 days on market
$425,000Price reduced by $14,900 on Nov 5, 2026
3531 Linnet CourtKissimmee, FL, 34746
- 4 beds
- 3 baths
- 3,434 sqft
3 days on market
$430,000
1271 Grassland AvenueSt Cloud, FL, 34771
- 4 beds
- 2 baths
- 1,839 sqft
1 day on market
$345,000
4534 Oakbrook CourtKissimmee, FL, 34746
- 3 beds
- 2 baths
- 1,330 sqft
1 day on market
$199,000
0 Ham Brown RoadKissimmee, FL, 34746
- Land
- 1.13 acres
1 day on market
$349,000
811 Aspenwood CircleKissimmee, FL, 34743
- 3 beds
- 2 baths
- 1,362 sqft
1 day on market
$205,000
3001 Limbo Lane Unit 103Kissimmee, FL, 34746
- 1 bed
- 1 bath
- 809 sqft
15 days on market
$420,000
3012 Villa Preciosa DriveKissimmee, FL, 34744
- 4 beds
- 2 baths
- 2,074 sqft
126 days on market
$185,000Price reduced by $14,900 on Oct 15, 2026
1322 Seven Eagles Court Unit 102Reunion, FL, 34747
- 1 bed
- 1 bath
- 823 sqft
1 day on market
$399,900
1150 Marni Ridge CourtKissimmee, FL, 34747
- 3 beds
- 2 baths
- 1,971 sqft
Browse all listings3,538 listings

View matching Osceola County homes

Browse Osceola County homes by price

Available-feed asking-price bands. Each band changes the price range and retains the county, bedroom and property-type filters.

The wider county asking-price picture

As you compare Osceola County homes for sale under $500K, FL, we keep your filtered search separate from the wider market. The snapshot below covers all property types and asking prices across the full county. Its inventory count and median asking price describe that broader market, not your under-$500K results. Asking prices are sellers' advertised figures, not completed sale prices or evidence of what your budget typically buys.

Osceola County asking-inventory snapshot

Available-feed listings across the full county, all property types and prices. County context, not completed sales or this page's filtered subset.

For sale now: 4,901
Median asking price: $398,000

Different settings within one county search

Compare settings for everyday living or second-home use. These location features do not indicate under-$500K availability in every community.

Kissimmee: downtown and lakefront recreation
Between historic downtown and Lake Tohopekaliga, Kissimmee Lakefront Park offers public trails, playgrounds and a fishing pier for everyday outings.
St. Cloud: space for time outdoors
St. Cloud's public Lakefront Park has a marina, boat ramp, splash pad and more than two miles of bike path. Compare the route from each home.
Celebration and Harmony: different community settings
Consider Celebration's planned-community setting alongside Harmony's distinct residential setting. Compare daily routines, not assumed affordability.
SunRail: compare station access by address
Tupperware, Kissimmee/Amtrak and Poinciana are county SunRail stations. Check access from each address rather than assuming a walk or commute time.
Kenansville: a rural county setting
Rural Kenansville lies south of St. Cloud. Its community center and park include a playground, pavilion and meeting space for local recreation.

Purchase price versus the cost of owning

Use $500K as a search threshold, not a measure of value or luxury. Compare the purchase price with the responsibilities and recurring costs of each property.

Aspect	Budget item	What the asking price tells you	What to check separately
Price and condition	Purchase budget, repairs and the maintenance responsibilities you would take on.	The seller's advertised price, not the home's condition or the cost of future work.	Inspect condition; compare detached-home upkeep with the condo association's documented maintenance responsibilities.
Property taxes	First-year property taxes after your purchase, plus any applicable assessments.	Neither the asking price nor the seller's current tax bill establishes your future annual tax cost.	The county estimator is approximate and excludes non-ad valorem assessments and CDD fees.
Community charges	CDD infrastructure assessments and separate community association dues, where applicable.	A price below your ceiling does not tell you whether either charge applies to the property.	Review parcel tax statements and association charges separately; CDD assessments are set annually.
Insurance	Property-specific insurance, with attention to roof age, building systems, location and occupancy.	A lower asking price does not establish a lower premium or make a newer home cheaper to insure.	Obtain quotes; for condos, distinguish association master insurance from the unit coverage you need.
Flood exposure	Parcel-level flood exposure and separate flood insurance considerations.	The advertised price provides no assurance about flood exposure or what an insurance policy covers.	Check parcel flood mapping and coverage options. Standard homeowners insurance typically excludes flooding.

How to read Nearby sales

Nearby sales are completed transactions within a radius of a property returned by the Osceola County under-$500K search. They are not a complete countywide sales dataset, and the sold properties do not necessarily match the active search's price limit. Compare location, property type and condition before treating a nearby sale as relevant to your shortlist.

Nearby sold homes for comparison

22 properties sold within half a mile in the last 12 months · median $368,000

See all sold

3851 Gulf Shore Circle
4 bed · 2 bath · 2,165 sqft
$357,200
Sold Oct 30, 2026
3843 Golden Knot Drive
3 bed · 2 bath · 1,827 sqft
$374,987
Sold Oct 21, 2026
3856 Gulf Shore Circle
3 bed · 3 bath · 1,895 sqft
$340,000
Sold Sep 28, 2026
3978 Blossom Dew Drive
5 bed · 4 bath · 3,342 sqft
$500,000
Sold Sep 3, 2026

Questions about this county search

Gaby Sadler

Property Specialist, Serhant

Talk Osceola County homes below $500K

I can help you compare Osceola County locations below $500,000 while keeping the ongoing budget separate. We can identify association dues, applicable district charges and insurance questions before you settle on a shortlist.

+1 (407) 490-0475 realty@thetopvillas.com

Find the home that fits your priorities

We can help you compare current homes against the county setting you prefer, the upkeep you want to manage and the ongoing costs you need to plan for. Keep your purchase ceiling alongside those priorities, whether you want an everyday home or a second home. For broader location context, visit our Osceola County overview, then use your shortlist to compare individual properties in more detail.

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