Homes under $300K in Winter Haven, FL
333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 18 of 23
- 333 lake howard drive northwest 314d, Winter Haven 33880 Off market since Sep 2026 $99,000 · 3 bd · 2 ba · 1,226 sqft
- 3928 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $279,150 · 4 bd · 2 ba · 1,607 sqft
- 6 golfview circle northeast, Winter Haven 33881 Off market since Sep 2026 $299,900 · 3 bd · 3 ba · 1,892 sqft
- 996 summer glen drive, Winter Haven 33880 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,851 sqft
- 1026 medinah drive, Winter Haven 33884 Off market since Sep 2026 $172,500 · 2 bd · 2 ba · 1,398 sqft
- 2049 san marcos drive southeast 127, Winter Haven 33880 Off market since Sep 2026 $149,900 · 1 bd · 1 ba · 666 sqft
- 217 4th jpv street, Winter Haven 33880 Off market since Sep 2026 $229,900 · 3 bd · 1 ba · 1,064 sqft
- 719 avenue q southeast, Winter Haven 33880 Off market since Sep 2026 $220,000 · 2 bd · 2 ba · 1,181 sqft
- 4132 sprucewood street, Winter Haven 33880 Off market since Sep 2026 $129,000 · 2 bd · 2 ba · 1,344 sqft
- 204 avenue d northeast, Winter Haven 33881 Off market since Sep 2026 $250,000 · 6 bd · 3 ba · 2,102 sqft
- 265 majestic gardens lane, Winter Haven 33880 Off market since Sep 2026 $299,999 · 3 bd · 2 ba · 1,951 sqft
- 151 1st street, Winter Haven 33880 Off market since Sep 2026 $258,000 · 3 bd · 2 ba · 1,259 sqft
- 563 honey bell road, Winter Haven 33880 Off market since Sep 2026 $299,900 · 4 bd · 2 ba · 1,851 sqft
- 4158 rolling oaks drive, Winter Haven 33880 Off market since Sep 2026 $124,900 · 2 bd · 2 ba · 1,403 sqft
- 531 heather glen drive, Winter Haven 33884 Off market since Sep 2026 $265,000 · 3 bd · 2 ba · 1,535 sqft
- 4129 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $284,900 · 3 bd · 2 ba · 1,504 sqft
- 3184 royal tern drive, Winter Haven 33881 Off market since Sep 2026 $286,900 · 3 bd · 2 ba · 1,725 sqft
- 124 center street, Winter Haven 33880 Off market since Sep 2026 $165,000 · 3 bd · 2 ba · 1,306 sqft
- 381 san jose drive, Winter Haven 33884 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,651 sqft
- 3357 timberline road west, Winter Haven 33880 Off market since Sep 2026 $265,000 · 4 bd · 2 ba · 1,675 sqft
- 3467 julius estates boulevard, Winter Haven 33881 Off market since Sep 2026 $269,000 · 3 bd · 2 ba · 1,750 sqft
- 140 krenson bay loop, Winter Haven 33881 Off market since Aug 2026 $270,000 · 3 bd · 2 ba · 1,479 sqft
- 6733 kensington drive northeast, Winter Haven 33881 Off market since Aug 2026 $175,000 · 2 bd · 2 ba · 1,224 sqft
- 700 mirror terrace northwest 506, Winter Haven 33881 Off market since Sep 2026 $119,000 · 2 bd · 2 ba · 1,190 sqft
- 105 laurel cove way 105, Winter Haven 33884 Off market since Sep 2026 $199,000 · 2 bd · 2 ba · 1,090 sqft
- 3960 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $289,000 · 4 bd · 2 ba · 1,607 sqft
- 136 krenson bay loop, Winter Haven 33881 Off market since Sep 2026 $274,990 · 3 bd · 2 ba · 1,698 sqft
- 1303 northeast stately oaks drive northwest, Winter Haven 33881 Off market since Jul 2026 $279,000 · 3 bd · 2 ba · 1,693 sqft
- 645 broadmoor circle 645, Winter Haven 33884 Off market since Sep 2026 $169,000 · 2 bd · 2 ba · 1,278 sqft
- 3430 fox ridge street, Winter Haven 33884 Off market since Sep 2026 $239,000 · 3 bd · 2 ba · 1,369 sqft
- 1104 tyler loop, Winter Haven 33884 Off market since Sep 2026 $299,000 · 3 bd · 2 ba · 1,540 sqft
- 1680 32nd street northwest, Winter Haven 33881 Off market since Sep 2026 $190,000 · 3 bd · 1 ba · 1,104 sqft
- 345 avenue p northeast, Winter Haven 33881 Off market since Sep 2026 $189,000 · 3 bd · 1 ba · 744 sqft
- 1101 28th street northwest, Winter Haven 33881 Off market since Sep 2026 $200,999 · 2 bd · 1 ba · 968 sqft
- 6272 botticella boulevard, Winter Haven 33884 Sold on Aug 11, 2026 $289,490 · 5 bd · 3 ba · 2,112 sqft
- 2500 21st street northwest 22, Winter Haven 33881 Off market since Sep 2026 $178,990 · 2 bd · 3 ba · 1,334 sqft
- 435 16th street northeast, Winter Haven 33881 Off market since Sep 2026 $245,000 · 3 bd · 1 ba · 1,700 sqft
- 820 26th street northwest, Winter Haven 33881 Off market since Sep 2026 $249,000 · 3 bd · 2 ba · 1,122 sqft
- 509 sharon hill court, Winter Haven 33880 Off market since Sep 2026 $229,900 · 3 bd · 2 ba · 1,728 sqft
- 664 clubhouse road, Winter Haven 33884 Off market since Sep 2026 $235,000 · 2 bd · 2 ba · 1,395 sqft
- 4146 sprucewood street, Winter Haven 33880 Off market since Sep 2026 $140,000 · 2 bd · 2 ba · 1,344 sqft
- 108 edgewater drive, Winter Haven 33881 Off market since Sep 2026 $195,000 · 4 bd · 2 ba · 1,450 sqft
- 1605 36th street northwest, Winter Haven 33881 Off market since Sep 2026 $210,000 · 5 bd · 2 ba · 1,700 sqft
- 2095 west hartridge terrace, Winter Haven 33881 Off market since Sep 2026 $289,000 · 3 bd · 2 ba · 1,816 sqft
- 180 solis drive, Winter Haven 33880 Off market since Sep 2026 $268,520 · 3 bd · 2 ba · 1,460 sqft
- 2121 greenway drive, Winter Haven 33881 Off market since Sep 2026 $261,000 · 3 bd · 2 ba · 1,264 sqft
- 3025 captain jax way, Winter Haven 33884 Off market since Sep 2026 $245,140 · 3 bd · 3 ba · 1,423 sqft
- 4049 giorgio drive, Winter Haven 33884 Off market since Sep 2026 $286,900 · 3 bd · 2 ba · 1,504 sqft
- 1700 6th street northwest c21, Winter Haven 33881 Off market since Sep 2026 $92,000 · 2 bd · 2 ba · 840 sqft
- 622 crystals boulevard, Winter Haven 33884 Off market since Sep 2026 $229,500 · 3 bd · 2 ba · 1,328 sqft