4253 STAFFORD DRIVE
WINTER HAVEN, FL 33880
$275,000 · Active
3 beds · 2.5 baths · 2,631 sq ft
Under $300KWinter Haven
…room to entertain, and the opportunity to create something special—welcome to…
MLS #O6448269
Winter Haven Homes Under $300,000
Explore homes under $300,000 for sale in Winter Haven, Florida. Compare current listing photos, prices, and property details, then request a home tour.
This collection matches Winter Haven, Florida using MLS or standardized postal-city data.
464 listings match your search
Showing up to 24 listings. Availability and pricing can change.
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609 MAGGIE CIRCLE
WINTER HAVEN, FL 33880
$224,900 · Active
3 beds · 2 baths · 1,430 sq ft
Under $300KWinter Haven
MLS #TB8556441
2771 ADELINE AVENUE
WINTER HAVEN, FL 33881
$296,990 · Active
4 beds · 2 baths · 1,574 sq ft
Under $300KWinter Haven
MLS #O6449262
2767 ADELINE AVENUE
WINTER HAVEN, FL 33881
$298,990 · Active
4 beds · 2 baths · 1,574 sq ft
Under $300KWinter Haven
MLS #O6449271
86 LAKE DAISY BOULEVARD
WINTER HAVEN, FL 33884
$269,999 · Active
2 beds · 2 baths · 1,826 sq ft
Under $300KWinter Haven
…86 Lake Daisy Blvd in Winter Haven. Don’t let the two-bedroom count…
MLS #O6449313
2303 S SWAN COURT NE
WINTER HAVEN, FL 33881
$218,000 · Active
3 beds · 2 baths · 1,536 sq ft
Under $300KWinter Haven
…into this beautiful 4-bedroom, 2-bath Winter Haven home, offering a welcoming blend…
MLS #O6449346
444 AVENUE I SE
WINTER HAVEN, FL 33880
$119,000 · Active
2 beds · 2 baths · 1,036 sq ft
Under $300KWinter Haven
…can go toward finishes and value-adding improvements. Offering approximately 1,036 square…
MLS #TB8556320
2415 BRASSIE COURT
WINTER HAVEN, FL 33884
$279,000 · Active
3 beds · 2 baths · 1,629 sq ft
Under $300KWinter Haven
…Staged. Situated in desirable southeast Winter Haven, this EcoSmart 3-bedroom, 2-bath home…
MLS #P4940101
2433 AVENUE F NW
WINTER HAVEN, FL 33880
$294,997 · Active
3 beds · 2 baths · 1,270 sq ft
Under $300KWinter Haven
…Lakes, parks and recreational trails. Move-in ready and easy to show—schedule your…
MLS #S5159213
183 OSPREY HEIGHTS DRIVE
WINTER HAVEN, FL 33880
$189,900 · Active
3 beds · 2 baths · 1,426 sq ft
Under $300KWinter Haven
…ROOF installed in 2025 adds value and peace of mind The…
MLS #L4965534
732 BAYSIDE BOULEVARD
WINTER HAVEN, FL 33881
$281,900 · Active
3 beds · 2 baths · 1,486 sq ft
Under $300KWinter Haven
MLS #L4965670
113 NEMO LANE
WINTER HAVEN, FL 33881
$239,900 · Active
3 beds · 2.5 baths · 1,544 sq ft
Under $300KWinter Haven
…insulation, and a programmable thermostat. Move-in ready and easy to maintain.
MLS #L4965688
1831 CARNOSTIE ROAD
WINTER HAVEN, FL 33884
$279,000 · Active
4 beds · 2 baths · 1,680 sq ft
Under $300KWinter Haven
…this property presents an exceptional opportunity in one of Winter Haven’s…
MLS #O6447701
193 E SWEET CIRCLE
WINTER HAVEN, FL 33884
$110,000 · Active
2 beds · 2 baths · 1,300 sq ft
Under $300KWinter Haven
…Enjoy the convenience of a move in ready home in an active park…
MLS #P4940099
828 30TH STREET NW
WINTER HAVEN, FL 33881
$215,000 · Active
3 beds · 2 baths · 1,100 sq ft
Under $300KWinter Haven
…SYSTEM, AND NO HOA IN WINTER HAVEN! Cosmetic updates include new flooring,…
MLS #TB8555416
1331 HAINES DRIVE
WINTER HAVEN, FL 33881
$249,000 · Active
3 beds · 2 baths · 1,471 sq ft
Under $300KWinter Haven
…it offers both comfort and value. The upgraded kitchen is designed…
MLS #L4965468
200 EL CAMINO #106
WINTER HAVEN, FL 33884
$79,000 · Active
1 beds · 1 baths · 1,078 sq ft
Under $300KWinter Haven
…home. And there's even more value in the HOA fee. Water,…
MLS #G5118765
2426 6TH ST NE
WINTER HAVEN, FL 33881
$240,000 · Active
3 beds · 2 baths · 1,447 sq ft
Under $300KWinter Haven
…a functional layout, and the opportunity to make it your own…
MLS #S5159083
200 EL CAMINO DRIVE #102
WINTER HAVEN, FL 33884
$97,000 · Active
2 beds · 2 baths · 1,378 sq ft
Under $300KWinter Haven
MLS #K4903838
217 GROVE RIDGE DRIVE
WINTER HAVEN, FL 33880
$160,000 · Active
2 beds · 2 baths · 1,344 sq ft
Under $300KWinter Haven
HELLO INVESTOR OR FIRST TIME HOME BUYER DON'T MISS THIS…
MLS #L4964035
218 6TH JPV STREET
WINTER HAVEN, FL 33880
$255,000 · Active
3 beds · 2 baths · 1,228 sq ft
Under $300KWinter Haven
MLS #P4940098
988 CAMBRIDGE DRIVE
WINTER HAVEN, FL 33881
$299,900 · Active
4 beds · 2 baths · 1,867 sq ft
Under $300KWinter Haven
…YOUR ELECTRIC BILL! This 2021-built Winter Haven home with LOW HOA's comes…
MLS #A4708281
2352 ISLE ROYALE COURT SE
WINTER HAVEN, FL 33880
$217,000 · Active
2 beds · 2.5 baths · 1,281 sq ft
Under $300KWinter Haven
…Florida home, or an investment opportunity, this townhouse combines comfort, convenience,…
MLS #L4965457
5101 MAGNOLIA PRESERVE BLVD
WINTER HAVEN, FL 33880
$259,900 · Active
3 beds · 3 baths · 1,394 sq ft
Under $300KWinter Haven
…This one gives you the opportunity to create your own. With…
MLS #S5158837