Holiday Homes for Sale under $500K

278 listings
2811 RAVENDALE LANE, HOLIDAY, FL 34691
24 Days on Market

House for Sale

$488,000

4 bd · 2 ba · 2,366 sqft

2811 RAVENDALE LANE, HOLIDAY, FL 34691

1166 CHANCELLOR DRIVE, HOLIDAY, FL 34690
Newly Listed

House for Sale

$479,900

4 bd · 3 ba · 1,761 sqft

1166 CHANCELLOR DRIVE, HOLIDAY, FL 34690

1125 FERNWOOD DRIVE, HOLIDAY, FL 34690
140 Days on Market

House for Sale

$474,900

3 bd · 2 ba · 1,900 sqft

1125 FERNWOOD DRIVE, HOLIDAY, FL 34690

3022 JACKSON DRIVE, HOLIDAY, FL 34691
143 Days on Market

House for Sale

$450,000

4 bd · 2 ba · 1,837 sqft

3022 JACKSON DRIVE, HOLIDAY, FL 34691

3549 ROCKAWAY DRIVE, HOLIDAY, FL 34691
39 Days on Market

House for Sale

$449,000

5 bd · 3 ba · 2,122 sqft

3549 ROCKAWAY DRIVE, HOLIDAY, FL 34691

5311 BOARDWALK STREET, HOLIDAY, FL 34690
121 Days on Market

Townhome for Sale

$447,400

3 bd · 3 ba · 1,848 sqft

5311 BOARDWALK STREET, HOLIDAY, FL 34690

1240 TRUNKFISH DRIVE, HOLIDAY, FL 34690
Newly Listed

House for Sale

$441,000

3 bd · 3 ba · 1,896 sqft

1240 TRUNKFISH DRIVE, HOLIDAY, FL 34690

2713 SAN LUIS ROAD, HOLIDAY, FL 34691
70 Days on Market

House for Sale

$430,000

3 bd · 2 ba · 1,460 sqft

2713 SAN LUIS ROAD, HOLIDAY, FL 34691

1316 BLUE MARLIN BOULEVARD, HOLIDAY, FL 34691
34 Days on Market

House for Sale

$425,000

4 bd · 3 ba · 2,638 sqft

1316 BLUE MARLIN BOULEVARD, HOLIDAY, FL 34691

2700 SIERRA VISTA WAY, HOLIDAY, FL 34691
112 Days on Market

House for Sale

$410,000

3 bd · 2 ba · 1,526 sqft

2700 SIERRA VISTA WAY, HOLIDAY, FL 34691

3708 HOLIDAY LAKE DRIVE, HOLIDAY, FL 34691
13 Days on Market

House for Sale

$399,990

4 bd · 3 ba · 2,002 sqft

3708 HOLIDAY LAKE DRIVE, HOLIDAY, FL 34691

2801 NARCISSUS DRIVE, HOLIDAY, FL 34691
Newly Listed

House for Sale

$399,900

4 bd · 2 ba · 1,720 sqft

2801 NARCISSUS DRIVE, HOLIDAY, FL 34691

4016 BADEN DRIVE, HOLIDAY, FL 34691
Newly Listed

House for Sale

$399,000

3 bd · 2 ba · 1,488 sqft

4016 BADEN DRIVE, HOLIDAY, FL 34691

5513 OCEANIC ROAD, HOLIDAY, FL 34690
Newly Listed

House for Sale

$385,000

4 bd · 3 ba · 1,800 sqft

5513 OCEANIC ROAD, HOLIDAY, FL 34690

3110 SHADOW OAKS DRIVE, HOLIDAY, FL 34690
30 Days on Market

House for Sale

$380,000

2 bd · 2 ba · 1,691 sqft

3110 SHADOW OAKS DRIVE, HOLIDAY, FL 34690

3645 OVERLAND, HOLIDAY, FL 34691
52 Days on Market

House for Sale

$364,900

3 bd · 3 ba · 1,416 sqft

3645 OVERLAND, HOLIDAY, FL 34691

2815 WOOD POINTE DRIVE, HOLIDAY, FL 34691
99 Days on Market

House for Sale

$359,900

3 bd · 2 ba · 1,819 sqft

2815 WOOD POINTE DRIVE, HOLIDAY, FL 34691

2906 WINDRIDGE DRIVE, HOLIDAY, FL 34691
351 Days on Market

House for Sale

$359,000

3 bd · 2 ba · 1,647 sqft

2906 WINDRIDGE DRIVE, HOLIDAY, FL 34691

5650 BITTERSWEET DRIVE, HOLIDAY, FL 34690
Newly Listed

House for Sale

$355,000

3 bd · 2 ba · 1,824 sqft

5650 BITTERSWEET DRIVE, HOLIDAY, FL 34690

2542 SANDY HILL COURT, HOLIDAY, FL 34691
10 Days on Market

House for Sale

$350,000

3 bd · 2 ba · 1,819 sqft

2542 SANDY HILL COURT, HOLIDAY, FL 34691

3652 WESTCHESTER DRIVE, HOLIDAY, FL 34691
Newly Listed

House for Sale

$350,000

3 bd · 3 ba · 2,197 sqft

3652 WESTCHESTER DRIVE, HOLIDAY, FL 34691

2514 SANDY HILL COURT, HOLIDAY, FL 34691
125 Days on Market

House for Sale

$345,900

2 bd · 2 ba · 1,555 sqft

2514 SANDY HILL COURT, HOLIDAY, FL 34691

1133 GRAND BOULEVARD, HOLIDAY, FL 34690
17 Days on Market

House for Sale

$339,000

3 bd · 2 ba · 1,496 sqft

1133 GRAND BOULEVARD, HOLIDAY, FL 34690

3222 JACKSON DRIVE, HOLIDAY, FL 34691
148 Days on Market

House for Sale

$339,000

2 bd · 2 ba · 1,126 sqft

3222 JACKSON DRIVE, HOLIDAY, FL 34691

Talk to a local agent

Looking at Holiday 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 Holiday, updated continuously. Florida Lux Real Estate currently tracks 278 active listings here. MLS inventory updated October 19, 2026.

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