Winter Haven Homes for Sale under $400K

718 listings
1144 HIGH SEAS STREET, WINTER HAVEN, FL 33880
25 Days on Market

House for Sale

$289,900

3 bd · 2 ba · 1,716 sqft

1144 HIGH SEAS STREET, WINTER HAVEN, FL 33880

3971 CYPRESS LANDING W, WINTER HAVEN, FL 33884
113 Days on Market

House for Sale

$289,900

3 bd · 2 ba · 1,674 sqft

3971 CYPRESS LANDING W, WINTER HAVEN, FL 33884

2128 BRETTON RIDGE BOULEVARD, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$289,900

4 bd · 2 ba · 1,560 sqft

2128 BRETTON RIDGE BOULEVARD, WINTER HAVEN, FL 33884

362 HOLLY RIDGE ROAD, WINTER HAVEN, FL 33880
18 Days on Market

House for Sale

$289,900

3 bd · 2 ba · 1,355 sqft

362 HOLLY RIDGE ROAD, WINTER HAVEN, FL 33880

1042 CORSO DRIVE, WINTER HAVEN, FL 33884
137 Days on Market

House for Sale

$289,900

4 bd · 2 ba · 1,730 sqft

1042 CORSO DRIVE, WINTER HAVEN, FL 33884

2791 ADELINE AVENUE, WINTER HAVEN, FL 33881
161 Days on Market

House for Sale

$289,740

4 bd · 2 ba · 1,498 sqft

2791 ADELINE AVENUE, WINTER HAVEN, FL 33881

913 EAGLE ROCK TERRACE, WINTER HAVEN, FL 33880
253 Days on Market

House for Sale

$289,500

4 bd · 2 ba · 1,728 sqft

913 EAGLE ROCK TERRACE, WINTER HAVEN, FL 33880

3307 COSTELLO CIRCLE, WINTER HAVEN, FL 33884
65 Days on Market

House for Sale

$289,000

3 bd · 2 ba · 1,553 sqft

3307 COSTELLO CIRCLE, WINTER HAVEN, FL 33884

2778 ADELINE AVENUE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$288,990

4 bd · 2 ba · 1,498 sqft

2778 ADELINE AVENUE, WINTER HAVEN, FL 33881

1660 HUMMINGBIRD ROAD, WINTER HAVEN, FL 33884
58 Days on Market

House for Sale

$288,900

3 bd · 2 ba · 1,593 sqft

1660 HUMMINGBIRD ROAD, WINTER HAVEN, FL 33884

3334 WHITE INDIGO ROAD, WINTER HAVEN, FL 33884
18 Days on Market

House for Sale

$288,900

3 bd · 2 ba · 1,504 sqft

3334 WHITE INDIGO ROAD, WINTER HAVEN, FL 33884

1085 BRENTON MANOR DRIVE, WINTER HAVEN, FL 33881
230 Days on Market

House for Sale

$288,500

3 bd · 2 ba · 1,770 sqft

1085 BRENTON MANOR DRIVE, WINTER HAVEN, FL 33881

4129 GIORGIO DRIVE, WINTER HAVEN, FL 33884
30 Days on Market

House for Sale

$287,990

3 bd · 2 ba · 1,504 sqft

4129 GIORGIO DRIVE, WINTER HAVEN, FL 33884

884 CAMBRIDGE DRIVE, WINTER HAVEN, FL 33881
68 Days on Market

House for Sale

$287,500

4 bd · 3 ba · 2,368 sqft

884 CAMBRIDGE DRIVE, WINTER HAVEN, FL 33881

4049 GIORGIO DRIVE, WINTER HAVEN, FL 33884
34 Days on Market

House for Sale

$286,990

3 bd · 2 ba · 1,504 sqft

4049 GIORGIO DRIVE, WINTER HAVEN, FL 33884

3184 ROYAL TERN DRIVE, WINTER HAVEN, FL 33881
38 Days on Market

House for Sale

$286,900

3 bd · 2 ba · 1,725 sqft

3184 ROYAL TERN DRIVE, WINTER HAVEN, FL 33881

3018 ROYAL TERN DRIVE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$285,999

3 bd · 2 ba · 1,690 sqft

3018 ROYAL TERN DRIVE, WINTER HAVEN, FL 33881

251 CALEB WAY, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$285,000

4 bd · 2 ba · 1,852 sqft

251 CALEB WAY, WINTER HAVEN, FL 33881

1831 CARNOSTIE ROAD, WINTER HAVEN, FL 33884
11 Days on Market

House for Sale

$285,000

4 bd · 2 ba · 1,680 sqft

1831 CARNOSTIE ROAD, WINTER HAVEN, FL 33884

108 EDGEWATER DRIVE, WINTER HAVEN, FL 33881
8 Days on Market

House for Sale

$285,000

4 bd · 2 ba · 1,450 sqft

108 EDGEWATER DRIVE, WINTER HAVEN, FL 33881

1966 WHITE HAWK WAY, WINTER HAVEN, FL 33881
50 Days on Market

House for Sale

$285,000

4 bd · 2 ba · 1,862 sqft

1966 WHITE HAWK WAY, WINTER HAVEN, FL 33881

200 BLACK SKIMMER LANE, WINTER HAVEN, FL 33880
246 Days on Market

House for Sale

$285,000

3 bd · 2 ba · 1,265 sqft

200 BLACK SKIMMER LANE, WINTER HAVEN, FL 33880

21 CASARENA COURT, WINTER HAVEN, FL 33881
161 Days on Market

House for Sale

$285,000

2 bd · 3 ba · 2,045 sqft

21 CASARENA COURT, WINTER HAVEN, FL 33881

105 BYRON PLACE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$285,000

4 bd · 2 ba · 1,836 sqft

105 BYRON PLACE, 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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