Winter Haven Homes for Sale under $400K

718 listings
531 HEATHER GLEN DRIVE, WINTER HAVEN, FL 33884
38 Days on Market

House for Sale

$265,000

3 bd · 2 ba · 1,535 sqft

531 HEATHER GLEN DRIVE, WINTER HAVEN, FL 33884

1973 CARNOSTIE ROAD, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$265,000

4 bd · 2 ba · 1,828 sqft

1973 CARNOSTIE ROAD, WINTER HAVEN, FL 33884

4140 SOPHIA BOULEVARD, WINTER HAVEN, FL 33880
108 Days on Market

House for Sale

$265,000

3 bd · 2 ba · 1,711 sqft

4140 SOPHIA BOULEVARD, WINTER HAVEN, FL 33880

3357 TIMBERLINE ROAD W, WINTER HAVEN, FL 33880
36 Days on Market

House for Sale

$265,000

4 bd · 2 ba · 1,675 sqft

3357 TIMBERLINE ROAD W, WINTER HAVEN, FL 33880

877 EAGLE ROCK TERRACE, WINTER HAVEN, FL 33880
Newly Listed

House for Sale

$265,000

3 bd · 2 ba · 1,312 sqft

877 EAGLE ROCK TERRACE, WINTER HAVEN, FL 33880

2362 BRASSIE COURT, WINTER HAVEN, FL 33884
144 Days on Market

House for Sale

$265,000

3 bd · 2 ba · 1,260 sqft

2362 BRASSIE COURT, WINTER HAVEN, FL 33884

3022 HICKORY STREET NW, WINTER HAVEN, FL 33881
177 Days on Market

House for Sale

$265,000

3 bd · 1 ba · 1,602 sqft

3022 HICKORY STREET NW, WINTER HAVEN, FL 33881

3936 GIORGIO DRIVE, WINTER HAVEN, FL 33884
49 Days on Market

House for Sale

$264,300

3 bd · 2 ba · 1,483 sqft

3936 GIORGIO DRIVE, WINTER HAVEN, FL 33884

2747 GLADIOLA ROAD, WINTER HAVEN, FL 33884
Newly Listed

Townhome for Sale

$263,990

3 bd · 3 ba · 1,673 sqft

2747 GLADIOLA ROAD, WINTER HAVEN, FL 33884

2753 GLADIOLA ROAD, WINTER HAVEN, FL 33884
Newly Listed

Townhome for Sale

$263,990

3 bd · 3 ba · 1,673 sqft

2753 GLADIOLA ROAD, WINTER HAVEN, FL 33884

2759 GLADIOLA ROAD, WINTER HAVEN, FL 33884
Newly Listed

Townhome for Sale

$263,990

3 bd · 3 ba · 1,673 sqft

2759 GLADIOLA ROAD, WINTER HAVEN, FL 33884

2765 GLADIOLA ROAD, WINTER HAVEN, FL 33884
Newly Listed

Townhome for Sale

$263,990

3 bd · 3 ba · 1,673 sqft

2765 GLADIOLA ROAD, WINTER HAVEN, FL 33884

3923 BALDWIN LANE, WINTER HAVEN, FL 33884
366 Days on Market

House for Sale

$263,900

3 bd · 2 ba · 1,719 sqft

3923 BALDWIN LANE, WINTER HAVEN, FL 33884

4019 CARTERET DRIVE, WINTER HAVEN, FL 33884
118 Days on Market

House for Sale

$262,500

2 bd · 2 ba · 1,719 sqft

4019 CARTERET DRIVE, WINTER HAVEN, FL 33884

909 CAMBRIDGE DRIVE, WINTER HAVEN, FL 33881
114 Days on Market

House for Sale

$261,900

3 bd · 2 ba · 1,506 sqft

909 CAMBRIDGE DRIVE, WINTER HAVEN, FL 33881

1473 LUCERNE LOOP ROAD NE, WINTER HAVEN, FL 33881
68 Days on Market

House for Sale

$260,000

4 bd · 2 ba · 1,599 sqft

1473 LUCERNE LOOP ROAD NE, WINTER HAVEN, FL 33881

1079 SUNSHINE WAY SW, WINTER HAVEN, FL 33880
Newly Listed

House for Sale

$260,000

3 bd · 2 ba · 1,348 sqft

1079 SUNSHINE WAY SW, WINTER HAVEN, FL 33880

2307 SCARLET AVENUE, WINTER HAVEN, FL 33884
280 Days on Market

House for Sale

$260,000

3 bd · 2 ba · 1,343 sqft

2307 SCARLET AVENUE, WINTER HAVEN, FL 33884

307 STERLING DRIVE, WINTER HAVEN, FL 33884
Newly Listed

House for Sale

$260,000

3 bd · 2 ba · 1,444 sqft

307 STERLING DRIVE, WINTER HAVEN, FL 33884

3856 GIORGIO DRIVE, WINTER HAVEN, FL 33884
26 Days on Market

House for Sale

$260,000

3 bd · 2 ba · 1,288 sqft

3856 GIORGIO DRIVE, WINTER HAVEN, FL 33884

1733 SANDALWOOD CIRCLE SW, WINTER HAVEN, FL 33880
145 Days on Market

House for Sale

$260,000

3 bd · 2 ba · 1,075 sqft

1733 SANDALWOOD CIRCLE SW, WINTER HAVEN, FL 33880

204 AVENUE D NE, WINTER HAVEN, FL 33881
63 Days on Market

House for Sale

$260,000

6 bd · 3 ba · 2,102 sqft

204 AVENUE D NE, WINTER HAVEN, FL 33881

352 VAIL DRIVE, WINTER HAVEN, FL 33884
48 Days on Market

House for Sale

$260,000

3 bd · 2 ba · 2,040 sqft

352 VAIL DRIVE, WINTER HAVEN, FL 33884

6056 NAVONA WAY, WINTER HAVEN, FL 33884
308 Days on Market

House for Sale

$259,999

3 bd · 2 ba · 1,615 sqft

6056 NAVONA 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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