Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 8 of 23

• 3588 raleigh drive, Winter Haven 33884 Pending $262,500 · 3 bd · 2 ba · 1,719 sqft
• 349 wharf way, Winter Haven 33881 Pending $249,900 · 3 bd · 3 ba · 1,604 sqft
• 3310 white indigo road, Winter Haven 33884 Pending $292,900 · 4 bd · 2 ba · 1,665 sqft
• 47 enclave drive, Winter Haven 33884 Pending $245,000 · 2 bd · 2 ba · 1,444 sqft
• 511 heather glen drive, Winter Haven 33884 Pending $282,000 · 4 bd · 2 ba · 1,488 sqft
• 29 enclave drive, Winter Haven 33884 Pending $245,000 · 3 bd · 2 ba · 1,526 sqft
• 3081 firebrush lane, Winter Haven 33884 Pending $263,900 · 3 bd · 2 ba · 1,302 sqft
• 1502 buckeye road northeast 4, Winter Haven 33881 Pending $189,900 · 2 bd · 2 ba · 1,257 sqft
• 6133 grand oaks drive southeast, Winter Haven 33884 Pending $149,900 · 2 bd · 2 ba · 1,234 sqft
• 2786 adeline avenue, Winter Haven 33881 Pending $295,990 · 4 bd · 2 ba · 1,498 sqft
• 2782 adeline avenue, Winter Haven 33881 Pending $266,900 · 3 bd · 2 ba · 1,328 sqft
• 3111 firebrush lane, Winter Haven 33884 Pending $278,990 · 3 bd · 2 ba · 1,302 sqft
• 2775 adeline avenue, Winter Haven 33881 Pending $268,900 · 3 bd · 2 ba · 1,328 sqft
• 936 avenue t southeast, Winter Haven 33880 Pending $220,900 · 3 bd · 2 ba · 1,410 sqft
• 4511 redwood street, Winter Haven 33880 Pending $110,000 · 2 bd · 2 ba · 1,152 sqft
• 4656 magnolia preserve loop, Winter Haven 33880 Pending $295,990 · 4 bd · 2 ba · 2,038 sqft
• 6010 navona way, Winter Haven 33884 Pending $279,999 · 3 bd · 2 ba · 1,615 sqft
• 6006 navona way, Winter Haven 33884 Pending $259,499 · 3 bd · 2 ba · 1,615 sqft
• 6775 brentwood drive northeast, Winter Haven 33881 Pending $132,500 · 3 bd · 2 ba · 1,320 sqft
• 100 el camino drive 101, Winter Haven 33884 Pending $74,900 · 2 bd · 2 ba · 1,361 sqft
• 1454 grand cayman circle, Winter Haven 33884 Pending $249,990 · 2 bd · 2 ba · 1,596 sqft
• 5561 taverna loop, Winter Haven 33884 Pending $274,900 · 3 bd · 2 ba · 1,504 sqft
• 6643 westchester drive northeast, Winter Haven 33881 Pending $174,900 · 2 bd · 2 ba · 1,456 sqft
• 1034 summer glen drive, Winter Haven 33880 Pending $267,000 · 3 bd · 2 ba · 1,847 sqft
• 1052 medinah drive, Winter Haven 33884 Pending $190,000 · 2 bd · 2 ba · 1,422 sqft
• 3040 captain jax way, Winter Haven 33884 Pending $247,490 · 3 bd · 3 ba · 1,423 sqft
• 3048 captain jax way, Winter Haven 33884 Pending $219,990 · 3 bd · 3 ba · 1,386 sqft
• 1715 sandalwood circle southwest, Winter Haven 33880 Pending $283,999 · 3 bd · 2 ba · 1,556 sqft
• 6212 botticella boulevard, Winter Haven 33884 Pending $289,490 · 5 bd · 3 ba · 2,112 sqft
• 443 ituna circle, Winter Haven 33881 Pending $298,900 · 3 bd · 2 ba · 1,644 sqft
• 23 casarena court, Winter Haven 33881 Pending $219,900 · 2 bd · 3 ba · 2,045 sqft
• 277 mariposa, Winter Haven 33884 Pending $215,000 · 2 bd · 2 ba · 1,142 sqft
• 245 16th street northeast, Winter Haven 33881 Pending $225,000 · 3 bd · 2 ba · 1,232 sqft
• 693 squires grove drive, Winter Haven 33880 Pending $220,000 · 3 bd · 2 ba · 1,690 sqft
• 333 lake howard drive northwest 203c, Winter Haven 33880 Pending $104,900 · 2 bd · 2 ba · 1,030 sqft
• 2015 6th street northeast, Winter Haven 33881 Pending $259,000 · 3 bd · 2 ba · 1,542 sqft
• 5121 sylas jax avenue, Winter Haven 33884 Pending $295,900 · 3 bd · 3 ba · 1,568 sqft
• 606 orange blossom drive, Winter Haven 33880 Pending $224,900 · 3 bd · 2 ba · 1,407 sqft
• 142 morning glory circle, Winter Haven 33884 Pending $284,500 · 3 bd · 2 ba · 1,887 sqft
• 3440 grenville drive, Winter Haven 33884 Pending $224,900 · 2 bd · 2 ba · 1,275 sqft
• 1373 lucerne loop road northeast, Winter Haven 33881 Pending $269,000 · 4 bd · 2 ba · 1,746 sqft
• 900 avenue z southeast d6, Winter Haven 33880 Pending $109,999 · 2 bd · 1 ba · 840 sqft
• 900 avenue z southeast a1, Winter Haven 33880 Pending $124,900 · 2 bd · 1 ba · 840 sqft
• 5041 kaia avenue, Winter Haven 33884 Pending $250,999 · 3 bd · 2 ba · 1,269 sqft
• 5029 kaia avenue, Winter Haven 33884 Pending $274,990 · 4 bd · 2 ba · 1,607 sqft
• 5013 kaia avenue, Winter Haven 33884 Pending $274,990 · 4 bd · 3 ba · 1,988 sqft
• 2953 whispering trails drive, Winter Haven 33884 Pending $230,000 · 3 bd · 2 ba · 1,274 sqft
• 430 hillcrest drive southeast, Winter Haven 33884 Pending $299,400 · 3 bd · 2 ba · 1,594 sqft
• 3865 giorgio drive, Winter Haven 33884 Pending $279,480 · 3 bd · 2 ba · 1,695 sqft
• 3214 avenue q northwest, Winter Haven 33881 Pending $164,900 · 2 bd · 1 ba · 936 sqft