Winter Haven Homes for Sale under $400K

718 listings
257 MEADOWBROOK BOULEVARD, WINTER HAVEN, FL 33881
194 Days on Market

House for Sale

$279,975

3 bd · 2 ba · 1,725 sqft

257 MEADOWBROOK BOULEVARD, WINTER HAVEN, FL 33881

511 MARCIA LOOP, WINTER HAVEN, FL 33884
253 Days on Market

House for Sale

$279,900

4 bd · 3 ba · 2,159 sqft

511 MARCIA LOOP, WINTER HAVEN, FL 33884

2799 ADELINE AVENUE, WINTER HAVEN, FL 33881
117 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,328 sqft

2799 ADELINE AVENUE, WINTER HAVEN, FL 33881

1787 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
251 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,526 sqft

1787 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884

1629 NANTUCKET WAY, WINTER HAVEN, FL 33884
73 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,526 sqft

1629 NANTUCKET WAY, WINTER HAVEN, FL 33884

4925 JACKSON STREET, WINTER HAVEN, FL 33884
23 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,425 sqft

4925 JACKSON STREET, WINTER HAVEN, FL 33884

1502 NE BUCKEYE ROAD NE # 2, WINTER HAVEN, FL 33881
14 Days on Market

Townhome for Sale

$279,900

3 bd · 3 ba · 2,004 sqft

1502 NE BUCKEYE ROAD NE # 2, WINTER HAVEN, FL 33881

1798 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884
74 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,526 sqft

1798 WHITE ELEPHANT LOOP, WINTER HAVEN, FL 33884

851 VIENNA DRIVE, WINTER HAVEN, FL 33884
48 Days on Market

House for Sale

$279,900

3 bd · 2 ba · 1,569 sqft

851 VIENNA DRIVE, WINTER HAVEN, FL 33884

6006 NAVONA WAY, WINTER HAVEN, FL 33884
135 Days on Market

House for Sale

$279,499

3 bd · 2 ba · 1,615 sqft

6006 NAVONA WAY, WINTER HAVEN, FL 33884

3027 RICHMOND DRIVE, WINTER HAVEN, FL 33884
94 Days on Market

House for Sale

$279,000

3 bd · 2 ba · 1,994 sqft

3027 RICHMOND DRIVE, WINTER HAVEN, FL 33884

4052 GIORGIO DRIVE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$275,900

3 bd · 2 ba · 1,504 sqft

4052 GIORGIO DRIVE, WINTER HAVEN, FL 33884

441 SAN JOSE DRIVE, WINTER HAVEN, FL 33884
416 Days on Market

House for Sale

$275,000

2 bd · 2 ba · 1,843 sqft

441 SAN JOSE DRIVE, WINTER HAVEN, FL 33884

137 LOWELL ROAD, WINTER HAVEN, FL 33884
42 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,435 sqft

137 LOWELL ROAD, WINTER HAVEN, FL 33884

415 8TH STREET NE, WINTER HAVEN, FL 33881
36 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,652 sqft

415 8TH STREET NE, WINTER HAVEN, FL 33881

1688 TEAGAN LANE, WINTER HAVEN, FL 33884
71 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,432 sqft

1688 TEAGAN LANE, WINTER HAVEN, FL 33884

428 MCKENNA DRIVE, WINTER HAVEN, FL 33881
9 Days on Market

House for Sale

$275,000

4 bd · 2 ba · 1,840 sqft

428 MCKENNA DRIVE, WINTER HAVEN, FL 33881

212 OVERLOOK DRIVE, WINTER HAVEN, FL 33884
17 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,731 sqft

212 OVERLOOK DRIVE, WINTER HAVEN, FL 33884

111 LAS FLORES, WINTER HAVEN, FL 33884
151 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,639 sqft

111 LAS FLORES, WINTER HAVEN, FL 33884

542 EAGLE LANDING BOULEVARD, WINTER HAVEN, FL 33880
111 Days on Market

House for Sale

$275,000

3 bd · 2 ba · 1,292 sqft

542 EAGLE LANDING BOULEVARD, WINTER HAVEN, FL 33880

Listing
72 Days on Market

House for Sale

$275,000

2 bd · 1 ba · 2,142 sqft

2021 OLIVER PLACE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$274,990

3 bd · 2 ba · 1,507 sqft

2021 OLIVER PLACE, WINTER HAVEN, FL 33881

1040 LUKE AVENUE, WINTER HAVEN, FL 33881
Newly Listed

House for Sale

$274,990

3 bd · 2 ba · 1,407 sqft

1040 LUKE AVENUE, WINTER HAVEN, FL 33881

136 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
53 Days on Market

House for Sale

$274,990

3 bd · 2 ba · 1,698 sqft

136 KRENSON BAY LOOP, WINTER HAVEN, FL 33881

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 718 active listings here. MLS inventory updated November 7, 2026.

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