Kissimmee Homes for Sale under $500K

2,205 listings
1383 LEVY BEND DRIVE, KISSIMMEE, FL 34744
Newly Listed

House for Sale

$500,000

4 bd · 3 ba · 2,102 sqft

1383 LEVY BEND DRIVE, KISSIMMEE, FL 34744

4460 NIRVANA PARKWAY, KISSIMMEE, FL 34746
76 Days on Market

House for Sale

$500,000

5 bd · 5 ba · 2,509 sqft

4460 NIRVANA PARKWAY, KISSIMMEE, FL 34746

3052 GATSBY STREET, KISSIMMEE, FL 34746
200 Days on Market

Townhome for Sale

$500,000

4 bd · 3 ba · 1,914 sqft

3052 GATSBY STREET, KISSIMMEE, FL 34746

2963 SERA BELLA WAY, KISSIMMEE, FL 34744
125 Days on Market

House for Sale

$500,000

3 bd · 3 ba · 2,416 sqft

2963 SERA BELLA WAY, KISSIMMEE, FL 34744

1733 BRIDGETS COURT, KISSIMMEE, FL 34744
Newly Listed

House for Sale

$500,000

4 bd · 3 ba · 2,665 sqft

1733 BRIDGETS COURT, KISSIMMEE, FL 34744

3092 ROCKEFELLER WAY, KISSIMMEE, FL 34747
23 Days on Market

Townhome for Sale

$500,000

4 bd · 6 ba · 2,356 sqft

3092 ROCKEFELLER WAY, KISSIMMEE, FL 34747

1672 TROPICAL PALMS CIRCLE, KISSIMMEE, FL 34747
Newly Listed

Townhome for Sale

$500,000

6 bd · 5 ba · 2,294 sqft

1672 TROPICAL PALMS CIRCLE, KISSIMMEE, FL 34747

158 BAREFOOT BEACH WAY, KISSIMMEE, FL 34746
120 Days on Market

House for Sale

$500,000

8 bd · 5 ba · 2,834 sqft

158 BAREFOOT BEACH WAY, KISSIMMEE, FL 34746

1980 SUMMER COURT, KISSIMMEE, FL 34744
115 Days on Market

House for Sale

$499,999

3 bd · 3 ba · 2,687 sqft

1980 SUMMER COURT, KISSIMMEE, FL 34744

3824 BLUE DASHER DRIVE, KISSIMMEE, FL 34744
391 Days on Market

House for Sale

$499,990

5 bd · 3 ba · 3,783 sqft

3824 BLUE DASHER DRIVE, KISSIMMEE, FL 34744

2466 RELAXING LANE, KISSIMMEE, FL 34744
11 Days on Market

House for Sale

$499,990

4 bd · 3 ba · 2,151 sqft

2466 RELAXING LANE, KISSIMMEE, FL 34744

2967 PENELOPE LOOP, KISSIMMEE, FL 34746
Newly Listed

Townhome for Sale

$499,990

4 bd · 3 ba · 1,914 sqft

2967 PENELOPE LOOP, KISSIMMEE, FL 34746

453 SORRENTO RD, KISSIMMEE, FL 34759
Newly Listed

House for Sale

$499,900

3 bd · 4 ba · 2,580 sqft

453 SORRENTO RD, KISSIMMEE, FL 34759

2163 COPPER BELL PLACE, KISSIMMEE, FL 34747
159 Days on Market

Townhome for Sale

$499,900

4 bd · 5 ba · 2,090 sqft

2163 COPPER BELL PLACE, KISSIMMEE, FL 34747

2464 WHITE POPPY DRIVE, KISSIMMEE, FL 34747
102 Days on Market

House for Sale

$499,900

5 bd · 4 ba · 2,845 sqft

2464 WHITE POPPY DRIVE, KISSIMMEE, FL 34747

5385 DAHLIA RESERVE DRIVE, KISSIMMEE, FL 34758
27 Days on Market

House for Sale

$499,900

6 bd · 3 ba · 2,658 sqft

5385 DAHLIA RESERVE DRIVE, KISSIMMEE, FL 34758

654 MADRID DRIVE, KISSIMMEE, FL 34758
Newly Listed

House for Sale

$499,900

4 bd · 3 ba · 3,226 sqft

654 MADRID DRIVE, KISSIMMEE, FL 34758

1889 RUSTIC FALLS DRIVE, KISSIMMEE, FL 34744
233 Days on Market

House for Sale

$499,900

4 bd · 4 ba · 3,099 sqft

1889 RUSTIC FALLS DRIVE, KISSIMMEE, FL 34744

2650 SANTOSH COVE, KISSIMMEE, FL 34746
29 Days on Market

House for Sale

$499,900

5 bd · 5 ba · 2,806 sqft

2650 SANTOSH COVE, KISSIMMEE, FL 34746

2821 SCENIC LANE, KISSIMMEE, FL 34744
100 Days on Market

House for Sale

$499,900

4 bd · 3 ba · 2,538 sqft

2821 SCENIC LANE, KISSIMMEE, FL 34744

8997 RHODES Street, Kissimmee, FL 34747
Newly Listed

House for Sale

$499,900

5 bd · 5.5 ba · 2,622 sqft

8997 RHODES Street, Kissimmee, FL 34747

2924 BOATING BOULEVARD, KISSIMMEE, FL 34746
256 Days on Market

House for Sale

$499,900

5 bd · 3 ba · 2,842 sqft

2924 BOATING BOULEVARD, KISSIMMEE, FL 34746

Listing
Newly Listed

House for Sale

$499,900

4 bd · 3 ba · 2,272 sqft

5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758
113 Days on Market

House for Sale

$499,000

4 bd · 3 ba · 2,847 sqft

5500 WILLOW BEND TRAIL, KISSIMMEE, FL 34758

Talk to a local agent

Looking at Kissimmee Homes for Sale under $500K?

Tell us what you're after — we'll send matching homes, off-market options and recent sales, and set up private showings.

Matthew Gromadzki, Real Estate Broker
Matthew Gromadzki
Real Estate Broker
(786) 370-8570
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Live MLS inventory in Kissimmee, updated continuously. Florida Lux Real Estate currently tracks 2,205 active listings here. MLS inventory updated October 12, 2026.

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