Winter Haven Homes for Sale under $400K

718 listings
4134 BEDFORD AVENUE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$309,000

3 bd · 2 ba · 1,941 sqft

4134 BEDFORD AVENUE, WINTER HAVEN, FL 33884

4669 OSPREY WAY, WINTER HAVEN, FL 33881
84 Days on Market

House for Sale

$309,000

4 bd · 2 ba · 1,992 sqft

4669 OSPREY WAY, WINTER HAVEN, FL 33881

2519 AVENUE E SW, WINTER HAVEN, FL 33880
Newly Listed

House for Sale

$309,000

3 bd · 2 ba · 1,675 sqft

2519 AVENUE E SW, WINTER HAVEN, FL 33880

5351 MICKEY AVENUE, WINTER HAVEN, FL 33884
261 Days on Market

House for Sale

$308,999

3 bd · 2 ba · 1,700 sqft

5351 MICKEY AVENUE, WINTER HAVEN, FL 33884

2523 AVENUE E SW, WINTER HAVEN, FL 33880
Newly Listed

House for Sale

$308,000

3 bd · 2 ba · 1,930 sqft

2523 AVENUE E SW, WINTER HAVEN, FL 33880

2795 ADELINE AVENUE, WINTER HAVEN, FL 33881
130 Days on Market

House for Sale

$305,740

5 bd · 2 ba · 1,708 sqft

2795 ADELINE AVENUE, WINTER HAVEN, FL 33881

981 HAROLD PASS, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$305,000

4 bd · 3 ba · 1,879 sqft

981 HAROLD PASS, WINTER HAVEN, FL 33884

144 WATERSIDE CIRCLE, WINTER HAVEN, FL 33880
16 Days on Market

House for Sale

$305,000

3 bd · 2 ba · 1,847 sqft

144 WATERSIDE CIRCLE, WINTER HAVEN, FL 33880

5780 LAKESIDE LANDINGS BOULEVARD, WINTER HAVEN, FL 33881
75 Days on Market

House for Sale

$305,000

4 bd · 3 ba · 2,526 sqft

5780 LAKESIDE LANDINGS BOULEVARD, WINTER HAVEN, FL 33881

621 VITTORIO DRIVE, WINTER HAVEN, FL 33884
362 Days on Market

House for Sale

$305,000

4 bd · 2 ba · 1,857 sqft

621 VITTORIO DRIVE, WINTER HAVEN, FL 33884

2579 SAGE VALLEY WAY, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$305,000

3 bd · 2 ba · 1,535 sqft

2579 SAGE VALLEY WAY, WINTER HAVEN, FL 33884

300 MEREDITH BOULEVARD, WINTER HAVEN, FL 33881
54 Days on Market

House for Sale

$304,990

4 bd · 2 ba · 1,758 sqft

300 MEREDITH BOULEVARD, WINTER HAVEN, FL 33881

1871 EMILY DRIVE, WINTER HAVEN, FL 33884
80 Days on Market

House for Sale

$304,900

4 bd · 2 ba · 2,012 sqft

1871 EMILY DRIVE, WINTER HAVEN, FL 33884

3815 POMELO, WINTER HAVEN, FL 33884
128 Days on Market

House for Sale

$304,900

3 bd · 2 ba · 1,672 sqft

3815 POMELO, WINTER HAVEN, FL 33884

951 LUNAR LANE, WINTER HAVEN, FL 33884
192 Days on Market

House for Sale

$304,016

3 bd · 2 ba · 1,447 sqft

951 LUNAR LANE, WINTER HAVEN, FL 33884

3905 OSPREY POINTE CIRCLE, WINTER HAVEN, FL 33884
86 Days on Market

House for Sale

$304,000

3 bd · 2 ba · 1,729 sqft

3905 OSPREY POINTE CIRCLE, WINTER HAVEN, FL 33884

1799 CARNOSTIE ROAD, WINTER HAVEN, FL 33884
111 Days on Market

House for Sale

$304,000

4 bd · 2 ba · 1,680 sqft

1799 CARNOSTIE ROAD, WINTER HAVEN, FL 33884

6249 BOTTICELLA BOULEVARD, WINTER HAVEN, FL 33884
10 Days on Market

House for Sale

$303,990

5 bd · 3 ba · 2,326 sqft

6249 BOTTICELLA BOULEVARD, WINTER HAVEN, FL 33884

3117 FIREBRUSH LANE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$303,990

4 bd · 2 ba · 1,665 sqft

3117 FIREBRUSH LANE, WINTER HAVEN, FL 33884

611 ITUNA CIRCLE, WINTER HAVEN, FL 33881
10 Days on Market

House for Sale

$303,900

3 bd · 2 ba · 1,644 sqft

611 ITUNA CIRCLE, WINTER HAVEN, FL 33881

757 REGGIE ROAD, WINTER HAVEN, FL 33884
296 Days on Market

House for Sale

$303,000

3 bd · 2 ba · 1,432 sqft

757 REGGIE ROAD, WINTER HAVEN, FL 33884

126 BERMUDA COURT, WINTER HAVEN, FL 33880
19 Days on Market

Home for Sale

$300,000

4 bd · 2 ba · 2,052 sqft

126 BERMUDA COURT, WINTER HAVEN, FL 33880

423 MAJESTIC GARDENS BLVD, WINTER HAVEN, FL 33880
75 Days on Market

House for Sale

$300,000

4 bd · 2 ba · 1,941 sqft

423 MAJESTIC GARDENS BLVD, WINTER HAVEN, FL 33880

132 LAKE MARIAM WAY, WINTER HAVEN, FL 33884
29 Days on Market

House for Sale

$300,000

4 bd · 2 ba · 2,207 sqft

132 LAKE MARIAM WAY, WINTER HAVEN, FL 33884

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Looking at Winter Haven Homes for Sale under $400K?

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 Winter Haven, updated continuously. Florida Lux Real Estate currently tracks 718 active listings here. MLS inventory updated November 7, 2026.

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