Winter Haven Homes for Sale under $400K

718 listings
607 COUNTRY LANE NE # 607, WINTER HAVEN, FL 33881
125 Days on Market

Condo for Sale

$142,500

2 bd · 2 ba · 1,252 sqft

607 COUNTRY LANE NE # 607, WINTER HAVEN, FL 33881

4146 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880
Newly Listed

Home for Sale

$140,000

2 bd · 2 ba · 1,344 sqft

4146 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880

6666 BRIARHILL DRIVE NE, WINTER HAVEN, FL 33881
Newly Listed

Home for Sale

$140,000

2 bd · 2 ba · 1,144 sqft

6666 BRIARHILL DRIVE NE, WINTER HAVEN, FL 33881

626 PAVARE COURT, WINTER HAVEN, FL 33884
31 Days on Market

Condo for Sale

$139,900

2 bd · 2 ba · 851 sqft

626 PAVARE COURT, WINTER HAVEN, FL 33884

4234 ROLLING OAKS DRIVE, WINTER HAVEN, FL 33880
Newly Listed

Home for Sale

$139,900

2 bd · 2 ba · 1,804 sqft

4234 ROLLING OAKS DRIVE, WINTER HAVEN, FL 33880

5850 CYPRESS GARDENS BOULEVARD # 304, WINTER HAVEN, FL 33884
481 Days on Market

Townhome for Sale

$139,000

2 bd · 2 ba · 1,332 sqft

5850 CYPRESS GARDENS BOULEVARD # 304, WINTER HAVEN, FL 33884

110 VALENCIA STREET, WINTER HAVEN, FL 33880
35 Days on Market

Home for Sale

$135,000

3 bd · 1 ba · 1,210 sqft

110 VALENCIA STREET, WINTER HAVEN, FL 33880

4212 CEDARWOOD STREET, WINTER HAVEN, FL 33880
91 Days on Market

Home for Sale

$133,900

2 bd · 2 ba · 1,265 sqft

4212 CEDARWOOD STREET, WINTER HAVEN, FL 33880

4880 OLD LUCERNE PARK ROAD, WINTER HAVEN, FL 33881
36 Days on Market

Home for Sale

$129,990

2 bd · 1 ba · 660 sqft

4880 OLD LUCERNE PARK ROAD, WINTER HAVEN, FL 33881

6033 GRAND OAKS DRIVE SE, WINTER HAVEN, FL 33884
234 Days on Market

Home for Sale

$129,900

2 bd · 2 ba · 1,120 sqft

6033 GRAND OAKS DRIVE SE, WINTER HAVEN, FL 33884

1100 MARTINIQUE DRIVE # 106, WINTER HAVEN, FL 33884
10 Days on Market

Condo for Sale

$129,500

2 bd · 1 ba · 826 sqft

1100 MARTINIQUE DRIVE # 106, WINTER HAVEN, FL 33884

4132 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880
38 Days on Market

Home for Sale

$129,000

2 bd · 2 ba · 1,344 sqft

4132 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880

4332 CHERRYWOOD STREET, WINTER HAVEN, FL 33880
Newly Listed

Home for Sale

$125,000

2 bd · 2 ba · 1,150 sqft

4332 CHERRYWOOD STREET, WINTER HAVEN, FL 33880

4239 CEDARWOOD STREET, WINTER HAVEN, FL 33880
159 Days on Market

Home for Sale

$125,000

2 bd · 2 ba · 1,368 sqft

4239 CEDARWOOD STREET, WINTER HAVEN, FL 33880

4918 ROSEWOOD STREET, WINTER HAVEN, FL 33880
40 Days on Market

Home for Sale

$125,000

2 bd · 2 ba · 1,008 sqft

4918 ROSEWOOD STREET, WINTER HAVEN, FL 33880

235 6TH STREET NW # 307, WINTER HAVEN, FL 33881
13 Days on Market

Condo for Sale

$125,000

1 bd · 1 ba · 714 sqft

235 6TH STREET NW # 307, WINTER HAVEN, FL 33881

1700 6TH STREET NW # B23, WINTER HAVEN, FL 33881
Newly Listed

Condo for Sale

$125,000

2 bd · 2 ba · 960 sqft

1700 6TH STREET NW # B23, WINTER HAVEN, FL 33881

900 AVENUE Z SE # A1, WINTER HAVEN, FL 33880
82 Days on Market

Condo for Sale

$124,900

2 bd · 1 ba · 840 sqft

900 AVENUE Z SE # A1, WINTER HAVEN, FL 33880

4158 ROLLING OAKS DRIVE, WINTER HAVEN, FL 33880
42 Days on Market

Home for Sale

$124,900

2 bd · 2 ba · 1,403 sqft

4158 ROLLING OAKS DRIVE, WINTER HAVEN, FL 33880

1103 CYPRESS GARDENS BOULEVARD # 13, WINTER HAVEN, FL 33884
Newly Listed

Condo for Sale

$124,800

1 bd · 1 ba · 475 sqft

1103 CYPRESS GARDENS BOULEVARD # 13, WINTER HAVEN, FL 33884

689 LAKE HOWARD DRIVE NW # 1E, WINTER HAVEN, FL 33880
428 Days on Market

Condo for Sale

$124,000

2 bd · 2 ba · 1,050 sqft

689 LAKE HOWARD DRIVE NW # 1E, WINTER HAVEN, FL 33880

4242 CEDARWOOD STREET, WINTER HAVEN, FL 33880
Newly Listed

Home for Sale

$120,000

2 bd · 2 ba · 1,056 sqft

4242 CEDARWOOD STREET, WINTER HAVEN, FL 33880

100 LAKESIDE RANCH DRIVE, WINTER HAVEN, FL 33881
370 Days on Market

Home for Sale

$120,000

2 bd · 2 ba · 1,176 sqft

100 LAKESIDE RANCH DRIVE, WINTER HAVEN, FL 33881

4155 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880
Newly Listed

Home for Sale

$120,000

2 bd · 2 ba · 1,200 sqft

4155 SPRUCEWOOD STREET, WINTER HAVEN, FL 33880

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 8, 2026.

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