Homes under $500K in Winter Haven, FL
540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 28 of 36
- 140 krenson bay loop, Winter Haven 33881 Off market since Aug 2026 $270,000 · 3 bd · 2 ba · 1,479 sqft
- 2610 san marco way, Winter Haven 33884 Off market since Sep 2026 $326,900 · 4 bd · 2 ba · 1,819 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
- 300 meredith boulevard, Winter Haven 33881 Off market since Sep 2026 $304,990 · 4 bd · 2 ba · 1,758 sqft
- 276 terranova boulevard, Winter Haven 33884 Off market since Aug 2026 $364,999 · 4 bd · 2 ba · 2,262 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
- 4253 stafford drive, Winter Haven 33880 Off market since Sep 2026 $369,800 · 3 bd · 3 ba · 2,631 sqft
- 1101 28th street northwest, Winter Haven 33881 Off market since Sep 2026 $200,999 · 2 bd · 1 ba · 968 sqft
- 937 cattleman street, Winter Haven 33881 Off market since Sep 2026 $340,000 · 4 bd · 2 ba · 1,828 sqft
- 0 38th street northwest, Winter Haven 33881 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,322 sqft
- 6272 botticella boulevard, Winter Haven 33884 Sold on Aug 11, 2026 $289,490 · 5 bd · 3 ba · 2,112 sqft
- 1620 17th street northwest, Winter Haven 33881 Off market since Sep 2026 $449,000 · 2 bd · 3 ba · 965 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
- 54 lake link circle southeast, Winter Haven 33884 Off market since Sep 2026 $329,900 · 3 bd · 2 ba · 1,752 sqft
- 2452 salzburg loop, Winter Haven 33884 Off market since Sep 2026 $300,000 · 2 bd · 2 ba · 1,729 sqft
- 136 lake mariam road southeast, Winter Haven 33884 Off market since Sep 2026 $385,000 · 4 bd · 3 ba · 2,356 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
- 199 8th street southeast, Winter Haven 33880 Off market since Sep 2026 $405,000 · 5 bd · 2 ba · 2,992 sqft
- 3614 plymouth drive, Winter Haven 33884 Off market since Sep 2026 $310,000 · 3 bd · 2 ba · 2,109 sqft
- 2820 san marco way east, Winter Haven 33884 Off market since Sep 2026 $335,900 · 4 bd · 4 ba · 2,227 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
- 528 mckenna drive, Winter Haven 33881 Off market since Sep 2026 $330,000 · 4 bd · 3 ba · 1,964 sqft
- 306 terranova boulevard, Winter Haven 33884 Off market since Sep 2026 $370,000 · 4 bd · 3 ba · 2,413 sqft
- 3025 captain jax way, Winter Haven 33884 Off market since Sep 2026 $245,140 · 3 bd · 3 ba · 1,423 sqft
- 516 reggie road, Winter Haven 33884 Off market since Jul 2026 $325,000 · 4 bd · 3 ba · 2,109 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
- 681 lake dexter circle, Winter Haven 33884 Off market since Jul 2026 $349,000 · 3 bd · 3 ba · 1,320 sqft
- 622 crystals boulevard, Winter Haven 33884 Off market since Sep 2026 $229,500 · 3 bd · 2 ba · 1,328 sqft
- 204 4th jpv street, Winter Haven 33880 Off market since Jul 2026 $175,000 · 3 bd · 2 ba · 1,068 sqft
- 3530 evening star drive, Winter Haven 33881 Off market since Sep 2026 $315,000 · 4 bd · 2 ba · 1,822 sqft
- 105 lake sears drive, Winter Haven 33880 Off market since Aug 2026 $279,900 · 3 bd · 2 ba · 1,513 sqft
- 1454 austin street, Winter Haven 33884 Off market since Sep 2026 $320,000 · 5 bd · 3 ba · 2,254 sqft