Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 13 of 36

• 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
• 2008 river hawk loop, Winter Haven 33880 Pending $385,000 · 3 bd · 2 ba · 2,032 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
• 5460 san pietro drive, Winter Haven 33884 Pending $319,499 · 4 bd · 3 ba · 2,038 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
• 5381 san pietro drive, Winter Haven 33884 Pending $333,999 · 4 bd · 3 ba · 2,226 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
• 423 majestic gardens boulevard, Winter Haven 33880 Pending $300,000 · 4 bd · 2 ba · 1,941 sqft
• 408 talamone drive, Winter Haven 33884 Pending $489,900 · 4 bd · 3 ba · 2,333 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
• 2217 knights road, Winter Haven 33880 Pending $102,000 · 2 bd · 2 ba · 1,252 sqft
• 5871 windridge drive, Winter Haven 33881 Pending $300,000 · 4 bd · 4 ba · 3,050 sqft
• 328 vail drive, Winter Haven 33884 Pending $300,000 · 3 bd · 2 ba · 1,712 sqft
• 1061 sandpiper loop, Winter Haven 33881 Pending $465,000 · 5 bd · 3 ba · 2,472 sqft
• 2115 kings crossing southwest, Winter Haven 33880 Pending $195,000 · 2 bd · 2 ba · 1,396 sqft
• 3032 captain jax way, Winter Haven 33884 Pending $220,240 · 3 bd · 3 ba · 1,386 sqft
• 3936 giorgio drive, Winter Haven 33884 Pending $254,300 · 3 bd · 2 ba · 1,483 sqft
• 980 wedgewood drive southeast, Winter Haven 33880 Pending $450,000 · 4 bd · 3 ba · 2,363 sqft
• 915 martin luther king boulevard northeast, Winter Haven 33881 Pending $199,900 · 3 bd · 2 ba · 1,602 sqft
• 5747 lake fox drive east, Winter Haven 33884 Pending $235,000 · 2 bd · 3 ba · 1,032 sqft
• 3742 fieldstone circle, Winter Haven 33881 Pending $300,000 · 3 bd · 2 ba · 1,919 sqft
• 4111 island lakes drive, Winter Haven 33881 Pending $399,900 · 3 bd · 2 ba · 1,998 sqft
• 4081 giorgio drive, Winter Haven 33884 Pending $279,900 · 3 bd · 2 ba · 1,504 sqft
• 4815 khloe court, Winter Haven 33884 Pending $278,900 · 3 bd · 2 ba · 1,504 sqft
• 5872 royal hills circle, Winter Haven 33881 Pending $290,000 · 4 bd · 2 ba · 1,730 sqft
• 448 ituna circle, Winter Haven 33881 Pending $308,900 · 3 bd · 2 ba · 1,744 sqft
• 5553 hogan lane, Winter Haven 33884 Pending $349,500 · 3 bd · 2 ba · 1,858 sqft
• 2500 21st street northwest 47, Winter Haven 33881 Pending $177,000 · 2 bd · 3 ba · 1,229 sqft
• 117 nemo lane, Winter Haven 33881 Pending $249,900 · 3 bd · 3 ba · 1,544 sqft
• 4201 shadow wood drive, Winter Haven 33880 Pending $289,900 · 3 bd · 2 ba · 1,860 sqft
• 288 meredith boulevard, Winter Haven 33881 Pending $284,990 · 4 bd · 2 ba · 1,625 sqft
• 304 meredith boulevard, Winter Haven 33881 Pending $319,990 · 4 bd · 3 ba · 2,110 sqft
• 333 lake howard drive northwest 312b, Winter Haven 33880 Pending $129,000 · 2 bd · 2 ba · 1,030 sqft
• 1114 30th street northwest, Winter Haven 33881 Pending $110,000 · 2 bd · 1 ba · 856 sqft
• 1819 sandhill lane, Winter Haven 33884 Pending $345,000 · 3 bd · 2 ba · 2,045 sqft