Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 12 of 36

• 2791 adeline avenue, Winter Haven 33881 Pending $289,740 · 4 bd · 2 ba · 1,498 sqft
• 2799 adeline avenue, Winter Haven 33881 Pending $275,900 · 3 bd · 2 ba · 1,328 sqft
• 3807 pomelo drive, Winter Haven 33880 Pending $307,900 · 3 bd · 2 ba · 1,672 sqft
• 6394 lolly bay loop northeast, Winter Haven 33881 Pending $179,900 · 2 bd · 2 ba · 1,620 sqft
• 3865 osprey pointe circle, Winter Haven 33884 Pending $255,000 · 3 bd · 2 ba · 1,603 sqft
• 4948 kaia, Winter Haven 33884 Pending $278,900 · 4 bd · 2 ba · 1,665 sqft
• 3105 firebrush lane, Winter Haven 33884 Pending $293,990 · 3 bd · 2 ba · 1,504 sqft
• 615 ituna circle east, Winter Haven 33881 Pending $339,900 · 5 bd · 4 ba · 2,227 sqft
• 137 nemo lane, Winter Haven 33881 Pending $254,900 · 3 bd · 3 ba · 1,544 sqft
• 337 meredith boulevard, Winter Haven 33881 Pending $284,990 · 3 bd · 2 ba · 1,480 sqft
• 3588 raleigh drive, Winter Haven 33884 Pending $262,500 · 3 bd · 2 ba · 1,719 sqft
• 1491 axel circle, Winter Haven 33880 Pending $475,900 · 5 bd · 3 ba · 3,022 sqft
• 241 greenfield road, Winter Haven 33884 Pending $334,950 · 2 bd · 2 ba · 2,523 sqft
• 349 wharf way, Winter Haven 33881 Pending $249,900 · 3 bd · 3 ba · 1,604 sqft
• 740 squires grove drive, Winter Haven 33880 Pending $350,000 · 5 bd · 3 ba · 2,616 sqft
• 3815 pomelo drive, Winter Haven 33884 Pending $302,000 · 3 bd · 2 ba · 1,672 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
• 688 augusta road, Winter Haven 33884 Pending $337,000 · 3 bd · 2 ba · 1,586 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
• 1790 white elephant loop, Winter Haven 33884 Pending $364,900 · 5 bd · 3 ba · 2,244 sqft
• 6133 grand oaks drive southeast, Winter Haven 33884 Pending $149,900 · 2 bd · 2 ba · 1,234 sqft
• 525 avenue a northeast, Winter Haven 33881 Pending $345,000 · 4 bd · 3 ba · 1,870 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
• 6457 domizio drive, Winter Haven 33884 Pending $305,990 · 5 bd · 3 ba · 2,326 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
• 129 morning glory circle, Winter Haven 33884 Pending $304,000 · 3 bd · 2 ba · 1,888 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
• 1739 upland lane, Winter Haven 33884 Pending $409,635 · 4 bd · 3 ba · 2,551 sqft