Kissimmee Homes for Sale under $5M

2,900 listings
2780 VICKIE COURT, KISSIMMEE, FL 34744
167 Days on Market

House for Sale

$3,499,000

10 bd · 8 ba · 9,881 sqft

2780 VICKIE COURT, KISSIMMEE, FL 34744

1890 SAHA COURT, KISSIMMEE, FL 34744
68 Days on Market

House for Sale

$2,450,000

7 bd · 7 ba · 7,247 sqft

1890 SAHA COURT, KISSIMMEE, FL 34744

7442 GATHERING COURT, KISSIMMEE, FL 34747
90 Days on Market

House for Sale

$2,274,900

10 bd · 10 ba · 5,563 sqft

7442 GATHERING COURT, KISSIMMEE, FL 34747

2794 HOLIDAY WOODS DRIVE, KISSIMMEE, FL 34744
Newly Listed

House for Sale

$2,250,000

4 bd · 3 ba · 2,970 sqft

2794 HOLIDAY WOODS DRIVE, KISSIMMEE, FL 34744

2477 SHANTI DRIVE, KISSIMMEE, FL 34746
126 Days on Market

House for Sale

$1,950,000

15 bd · 16 ba · 6,255 sqft

2477 SHANTI DRIVE, KISSIMMEE, FL 34746

2441 SHANTI DRIVE, KISSIMMEE, FL 34746
Newly Listed

House for Sale

$1,950,000

15 bd · 17 ba · 6,249 sqft

2441 SHANTI DRIVE, KISSIMMEE, FL 34746

4147 BOGGY CREEK ROAD, KISSIMMEE, FL 34744
547 Days on Market

House for Sale

$1,850,000

4 bd · 3 ba · 2,932 sqft

4147 BOGGY CREEK ROAD, KISSIMMEE, FL 34744

3880 SONOMA BOULEVARD, KISSIMMEE, FL 34741
373 Days on Market

House for Sale

$1,750,000

15 bd · 17 ba · 6,374 sqft

3880 SONOMA BOULEVARD, KISSIMMEE, FL 34741

7390 GATHERING COURT, KISSIMMEE, FL 34747
101 Days on Market

House for Sale

$1,750,000

5 bd · 6 ba · 4,615 sqft

7390 GATHERING COURT, KISSIMMEE, FL 34747

2437 SHANTI DRIVE, KISSIMMEE, FL 34746
90 Days on Market

House for Sale

$1,749,000

13 bd · 11 ba · 5,504 sqft

2437 SHANTI DRIVE, KISSIMMEE, FL 34746

7936 JACKS CLUB COURT, KISSIMMEE, FL 34747
76 Days on Market

House for Sale

$1,725,000

6 bd · 7 ba · 4,588 sqft

7936 JACKS CLUB COURT, KISSIMMEE, FL 34747

3820 SONOMA BOULEVARD, KISSIMMEE, FL 34741
Newly Listed

House for Sale

$1,690,000

15 bd · 16 ba · 6,249 sqft

3820 SONOMA BOULEVARD, KISSIMMEE, FL 34741

1886 PLEASANT HILL ROAD, KISSIMMEE, FL 34746
192 Days on Market

House for Sale

$1,650,000

3 bd · 2 ba · 1,170 sqft

1886 PLEASANT HILL ROAD, KISSIMMEE, FL 34746

3801 SONOMA BOULEVARD, KISSIMMEE, FL 34741
Newly Listed

House for Sale

$1,550,000

14 bd · 11 ba · 6,404 sqft

3801 SONOMA BOULEVARD, KISSIMMEE, FL 34741

7638 WHITEMARSH WAY, KISSIMMEE, FL 34747
103 Days on Market

House for Sale

$1,500,000

9 bd · 10 ba · 5,154 sqft

7638 WHITEMARSH WAY, KISSIMMEE, FL 34747

7626 WHITEMARSH WAY, KISSIMMEE, FL 34747
30 Days on Market

House for Sale

$1,499,700

9 bd · 10 ba · 5,154 sqft

7626 WHITEMARSH WAY, KISSIMMEE, FL 34747

2468 RAMA DRIVE, KISSIMMEE, FL 34746
30 Days on Market

House for Sale

$1,499,000

12 bd · 12 ba · 4,762 sqft

2468 RAMA DRIVE, KISSIMMEE, FL 34746

3870 SONOMA BLVD, KISSIMMEE, FL 34741
68 Days on Market

House for Sale

$1,490,000

15 bd · 16 ba · 6,249 sqft

3870 SONOMA BLVD, KISSIMMEE, FL 34741

3800 SONOMA BOULEVARD, KISSIMMEE, FL 34741
273 Days on Market

House for Sale

$1,480,000

15 bd · 16 ba · 6,249 sqft

3800 SONOMA BOULEVARD, KISSIMMEE, FL 34741

7491 GATHERING DRIVE, KISSIMMEE, FL 34747
Newly Listed

House for Sale

$1,425,000

5 bd · 5 ba · 4,664 sqft

7491 GATHERING DRIVE, KISSIMMEE, FL 34747

1524 EUSTON DR, KISSIMMEE, FL 34747
Newly Listed

House for Sale

$1,400,000

5 bd · 6 ba · 3,775 sqft

1524 EUSTON DR, KISSIMMEE, FL 34747

840 SPINNAKER WAY, KISSIMMEE, FL 34746
171 Days on Market

House for Sale

$1,399,999

5 bd · 6 ba · 5,428 sqft

840 SPINNAKER WAY, KISSIMMEE, FL 34746

311 REEVES STREET, KISSIMMEE, FL 34747
42 Days on Market

House for Sale

$1,399,000

5 bd · 4 ba · 3,668 sqft

311 REEVES STREET, KISSIMMEE, FL 34747

801 GOLDEN BEAR DRIVE, KISSIMMEE, FL 34747
276 Days on Market

House for Sale

$1,385,000

6 bd · 6 ba · 3,428 sqft

801 GOLDEN BEAR DRIVE, KISSIMMEE, FL 34747

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Looking at Kissimmee Homes for Sale under $5M?

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 2,900 active listings here. MLS inventory updated October 11, 2026.

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