Winter Haven Homes for Sale under $400K

719 listings
2759 ADELINE AVENUE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$326,990

4 bd · 2 ba · 1,828 sqft

2759 ADELINE AVENUE, WINTER HAVEN, FL 33881

1739 UPLAND LANE, WINTER HAVEN, FL 33884
99 Days on Market

House for Sale

$326,990

3 bd · 2 ba · 1,815 sqft

1739 UPLAND LANE, WINTER HAVEN, FL 33884

5568 TAVERNA LOOP, WINTER HAVEN, FL 33884
8 Days on Market

House for Sale

$325,990

5 bd · 3 ba · 2,447 sqft

5568 TAVERNA LOOP, WINTER HAVEN, FL 33884

1122 BRIMSTONE CIR, WINTER HAVEN, FL 33884
295 Days on Market

House for Sale

$325,000

3 bd · 2 ba · 1,690 sqft

1122 BRIMSTONE CIR, WINTER HAVEN, FL 33884

129 LAKE OTIS ROAD SE, WINTER HAVEN, FL 33884
194 Days on Market

House for Sale

$325,000

5 bd · 3 ba · 2,579 sqft

129 LAKE OTIS ROAD SE, WINTER HAVEN, FL 33884

1836 CARNOSTIE ROAD, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$325,000

4 bd · 3 ba · 2,200 sqft

1836 CARNOSTIE ROAD, WINTER HAVEN, FL 33884

503 AVENUE B NW # 503, WINTER HAVEN, FL 33881
Newly Listed

Townhome for Sale

$325,000

2 bd · 3 ba · 1,408 sqft

503 AVENUE B NW # 503, WINTER HAVEN, FL 33881

2849 CATHY BOULEVARD, WINTER HAVEN, FL 33880
131 Days on Market

House for Sale

$325,000

4 bd · 2 ba · 1,928 sqft

2849 CATHY BOULEVARD, WINTER HAVEN, FL 33880

6115 GREY HERON DRIVE, WINTER HAVEN, FL 33881
13 Days on Market

House for Sale

$325,000

5 bd · 3 ba · 2,674 sqft

6115 GREY HERON DRIVE, WINTER HAVEN, FL 33881

319 NIBLICK CIRCLE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$325,000

2 bd · 2 ba · 1,647 sqft

319 NIBLICK CIRCLE, WINTER HAVEN, FL 33881

5264 GREEN DRIVE, WINTER HAVEN, FL 33884
127 Days on Market

House for Sale

$325,000

3 bd · 2 ba · 2,011 sqft

5264 GREEN DRIVE, WINTER HAVEN, FL 33884

1450 W LAKE CANNON DRIVE NW, WINTER HAVEN, FL 33881
123 Days on Market

House for Sale

$325,000

5 bd · 2 ba · 4,053 sqft

1450 W LAKE CANNON DRIVE NW, WINTER HAVEN, FL 33881

4913 KAIA AVENUE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$325,000

3 bd · 2 ba · 1,300 sqft

4913 KAIA AVENUE, WINTER HAVEN, FL 33884

731 CANBERRA ROAD, WINTER HAVEN, FL 33884
198 Days on Market

House for Sale

$325,000

3 bd · 2 ba · 2,140 sqft

731 CANBERRA ROAD, WINTER HAVEN, FL 33884

5394 SAN PIETRO DRIVE, WINTER HAVEN, FL 33884
25 Days on Market

House for Sale

$324,999

4 bd · 3 ba · 2,039 sqft

5394 SAN PIETRO DRIVE, WINTER HAVEN, FL 33884

2230 W CENTRAL AVENUE, WINTER HAVEN, FL 33880
30 Days on Market

House for Sale

$324,700

3 bd · 2 ba · 1,788 sqft

2230 W CENTRAL AVENUE, WINTER HAVEN, FL 33880

1508 MAJESTIC LANE, WINTER HAVEN, FL 33880
45 Days on Market

House for Sale

$324,500

4 bd · 3 ba · 1,900 sqft

1508 MAJESTIC LANE, WINTER HAVEN, FL 33880

3748 GIORGIO DRIVE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$324,490

4 bd · 2 ba · 1,828 sqft

3748 GIORGIO DRIVE, WINTER HAVEN, FL 33884

2240 LABRADOR LOOP, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$323,965

3 bd · 2 ba · 1,549 sqft

2240 LABRADOR LOOP, WINTER HAVEN, FL 33884

5147 KINSLEY DRIVE, WINTER HAVEN, FL 33884
437 Days on Market

House for Sale

$323,635

4 bd · 2 ba · 1,919 sqft

5147 KINSLEY DRIVE, WINTER HAVEN, FL 33884

2748 SAN MARCO WAY, WINTER HAVEN, FL 33884
48 Days on Market

House for Sale

$323,250

3 bd · 2 ba · 1,734 sqft

2748 SAN MARCO WAY, WINTER HAVEN, FL 33884

6064 NAVONA WAY, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$321,490

4 bd · 3 ba · 2,305 sqft

6064 NAVONA WAY, WINTER HAVEN, FL 33884

233 MANDOLIN DRIVE, WINTER HAVEN, FL 33884
22 Days on Market

House for Sale

$320,000

4 bd · 2 ba · 1,767 sqft

233 MANDOLIN DRIVE, WINTER HAVEN, FL 33884

329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884
81 Days on Market

House for Sale

$320,000

3 bd · 2 ba · 1,563 sqft

329 LAKE DAISY LOOP, WINTER HAVEN, FL 33884

Talk to a local agent

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 719 active listings here. MLS inventory updated November 6, 2026.

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