71 Days on Market
House for Sale
$274,990
4 bd · 2 ba · 1,607 sqft
Bedrooms
Bathrooms
Winter Haven Homes for Sale under $400K
718 listings
78 Days on Market
House for Sale
$274,900
4 bd · 2 ba · 1,743 sqft
262 OLEANDER STREET, WINTER HAVEN, FL 33881
Newly Listed
House for Sale
$274,900
3 bd · 2 ba · 1,302 sqft
3328 WHITE INDIGO ROAD, WINTER HAVEN, FL 33884
35 Days on Market
House for Sale
$274,190
3 bd · 2 ba · 1,695 sqft
3932 GIORGIO DRIVE, WINTER HAVEN, FL 33884
23 Days on Market
House for Sale
$274,000
3 bd · 2 ba · 1,873 sqft
5811 MARSH LANDING DRIVE, WINTER HAVEN, FL 33881
Newly Listed
Townhome for Sale
$273,990
3 bd · 3 ba · 1,758 sqft
2741 GLADIOLA ROAD, WINTER HAVEN, FL 33884
Newly Listed
Townhome for Sale
$273,990
3 bd · 3 ba · 1,758 sqft
2771 GLADIOLA ROAD, WINTER HAVEN, FL 33884
44 Days on Market
House for Sale
$272,500
4 bd · 2 ba · 1,583 sqft
780 OVERLOOK GROVE DRIVE, WINTER HAVEN, FL 33884
142 Days on Market
House for Sale
$270,000
4 bd · 2 ba · 1,846 sqft
920 CAMBRIDGE DR, Winter Haven, FL 33881
WINDRIDGE
Newly Listed
House for Sale
$270,000
3 bd · 2 ba · 1,172 sqft
1557 N LAKE SHIPP DRIVE SW, WINTER HAVEN, FL 33880
297 Days on Market
Home for Sale
$270,000
3 bd · 2 ba · 1,666 sqft
2817 WINGFOOT COURT, WINTER HAVEN, FL 33884
14 Days on Market
House for Sale
$270,000
3 bd · 2 ba · 1,491 sqft
233 KENSINGTON VIEW BOULEVARD, WINTER HAVEN, FL 33880
55 Days on Market
House for Sale
$270,000
3 bd · 2 ba · 1,479 sqft
140 KRENSON BAY LOOP, WINTER HAVEN, FL 33881
63 Days on Market
House for Sale
$270,000
3 bd · 2 ba · 1,065 sqft
1716 TERRY CIRCLE NE, WINTER HAVEN, FL 33881
Newly Listed
House for Sale
$270,000
3 bd · 2 ba · 1,848 sqft
615 AVENUE A NE, WINTER HAVEN, FL 33881
173 Days on Market
House for Sale
$269,999
3 bd · 2 ba · 1,453 sqft
541 HEATHER GLEN DR, WINTER HAVEN, FL 33884
Newly Listed
House for Sale
$269,990
3 bd · 2 ba · 1,302 sqft
5580 TAVERNA LOOP, WINTER HAVEN, FL 33884
Newly Listed
House for Sale
$269,990
3 bd · 3 ba · 1,408 sqft
811 22ND STREET NW, WINTER HAVEN, FL 33881
12 Days on Market
House for Sale
$269,900
3 bd · 2 ba · 1,738 sqft
118 BROWNING CIRCLE, WINTER HAVEN, FL 33884
105 Days on Market
House for Sale
$269,900
3 bd · 2 ba · 1,328 sqft
2790 ADELINE AVENUE, WINTER HAVEN, FL 33881
30 Days on Market
House for Sale
$269,000
3 bd · 3 ba · 1,685 sqft
110 MORNING GLORY CIRCLE, WINTER HAVEN, FL 33884
113 Days on Market
House for Sale
$269,000
3 bd · 2 ba · 1,688 sqft
440 KENSINGTON VIEW DRIVE, WINTER HAVEN, FL 33880
34 Days on Market
House for Sale
$268,520
3 bd · 2 ba · 1,460 sqft
180 SOLIS DRIVE, WINTER HAVEN, FL 33880
120 Days on Market
House for Sale
$268,000
3 bd · 2 ba · 1,470 sqft
1727 SECOND STREET NE, 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.
Live MLS inventory in Winter Haven, updated continuously. Florida Lux Real Estate currently tracks 718 active listings here. MLS inventory updated November 7, 2026.
Discover Your Perfect Home
Homes for Sale under $400K in Nearby Cities
Select Property Type
Winter Haven Condos for Sale by Type & Price
Bedroom Size Homes in Winter Haven
Homes by Price in Winter Haven
Lifestyle & New in Winter Haven
Rentals in Winter Haven
Homes Nearby Winter Haven: Neighborhoods
- INWOOD Homes for Sale(28)
- OAKWOOD ESTATES Homes for Sale(23)
- VILLAMAR Homes for Sale(22)
- HARMONY ON LAKE ELOISE Homes for Sale(19)
- LUCERNE PARK RESERVE Homes for Sale(14)
Show more (10)Show less
- GARDEN GROVE OAKS Homes for Sale(10)
- VILLA MAR Homes for Sale(10)
- JAN PHYL VILLAGE Homes for Sale(9)
- SEASONS AT ANNABELLE ESTATES Homes for Sale(9)
- WILLOWBROOK NORTH Homes for Sale(9)
- LAKE ASHTON WEST PH 01 Homes for Sale(8)
- WILLOWBROOK SOUTH Homes for Sale(8)
- WINTER HAVEN HARBOUR APTS CONDO Homes for Sale(8)
- ASHTON COVEY Homes for Sale(7)
- FLA HIGHLANDS CO SUB Homes for Sale(7)
Homes Nearby Winter Haven: Cities
Homes Nearby Winter Haven: ZIP Codes
- 33884 Homes for Sale(383)
- 33881 Homes for Sale(304)
- 33880 Homes for Sale(223)
- 33839 Homes for Sale(68)
- 33823 Homes for Sale(292)