Homes under $500K in Winter Haven, FL
733 homes for sale · Updated August 12, 2026 · Page 8 of 15
- 154 2nd street southwest unit 7, Winter Haven 33880 $495,000 · 2 bd · 3 ba · 1,640 sqft
- 2122 river hawk loop, Winter Haven 33880 $344,900 · 4 bd · 2 ba · 1,741 sqft
- 5780 lakeside landings boulevard, Winter Haven 33881 $305,000 · 4 bd · 3 ba · 2,526 sqft
- 3365 costello circle, Winter Haven 33884 $285,000 · 5 bd · 3 ba · 2,522 sqft
- 1709 teagan lane, Winter Haven 33884 $248,000 · 3 bd · 1 ba · 1,060 sqft
- 3865 giorgio drive, Winter Haven 33884 $284,480 · 3 bd · 2 ba · 1,695 sqft
- 3214 avenue q northwest, Winter Haven 33881 $164,900 · 2 bd · 1 ba · 936 sqft
- 931 whisper lake drive, Winter Haven 33880 $293,500 · 3 bd · 3 ba · 1,260 sqft
- 2121 river hawk loop, Winter Haven 33880 $342,900 · 3 bd · 2 ba · 1,741 sqft
- 5871 windridge drive, Winter Haven 33881 $329,100 · 4 bd · 4 ba · 3,050 sqft
- 5118 kinsley drive, Winter Haven 33884 $418,950 · 5 bd · 4 ba · 3,030 sqft
- 5110 kinsley drive, Winter Haven 33884 $399,999 · 5 bd · 4 ba · 3,030 sqft
- 150 el dorado 105, Winter Haven 33884 $98,500 · 2 bd · 2 ba · 1,372 sqft
- 292 krenson bay loop, Winter Haven 33881 $329,900 · 4 bd · 2 ba · 1,820 sqft
- 1508 majestic lane, Winter Haven 33880 $324,500 · 4 bd · 3 ba · 1,900 sqft
- 4130 bedford avenue, Winter Haven 33884 $309,900 · 2 bd · 2 ba · 1,819 sqft
- 1774 white elephant loop, Winter Haven 33884 $364,900 · 5 bd · 3 ba · 2,336 sqft
- 603 maggie circle, Winter Haven 33880 $255,000 · 3 bd · 2 ba · 1,482 sqft
- 328 vail drive, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 1,712 sqft
- 124 6th wahneta street west, Winter Haven 33880 $92,000 · 3 bd · 2 ba · 868 sqft
- 622 ridge terrace, Winter Haven 33881 $150,000 · 2 bd · 2 ba · 1,073 sqft
- 811 andrew street, Winter Haven 33881 $319,990 · 3 bd · 2 ba · 1,600 sqft
- 1688 teagan lane, Winter Haven 33884 $275,000 · 3 bd · 2 ba · 1,432 sqft
- 1406 meadow drive northeast, Winter Haven 33881 $225,000 · 3 bd · 2 ba · 1,678 sqft
- 3311 queens cove loop, Winter Haven 33880 $239,999 · 3 bd · 2 ba · 1,109 sqft
- 307 sterling drive, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 1,444 sqft
- 215 kilmer lane, Winter Haven 33884 $379,998 · 4 bd · 3 ba · 1,680 sqft
- 820 avenue z northwest, Winter Haven 33881 $197,500 · 3 bd · 2 ba · 2,082 sqft
- 2207 avenue f northwest, Winter Haven 33880 $249,900 · 3 bd · 2 ba · 1,310 sqft
- 3408 costello circle, Winter Haven 33884 $315,000 · 4 bd · 2 ba · 1,713 sqft
- 4519 rapallo avenue, Winter Haven 33884 $334,900 · 4 bd · 3 ba · 2,074 sqft
- 134 lake hazel drive, Winter Haven 33884 $90,000 · 2 bd · 2 ba · 1,352 sqft
- 5312 nicklaus drive, Winter Haven 33884 $334,900 · 3 bd · 2 ba · 1,700 sqft
- 704 eagle pond drive 704, Winter Haven 33884 $176,900 · 2 bd · 2 ba · 1,017 sqft
- 2115 kings crossing southwest, Winter Haven 33880 $215,000 · 2 bd · 2 ba · 1,396 sqft
- 700 mirror terrace northwest 507, Winter Haven 33881 $164,900 · 2 bd · 2 ba · 1,351 sqft
- 3268 country walk club circle, Winter Haven 33881 $295,000 · 3 bd · 2 ba · 1,690 sqft
- 2108 cartgate lane, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 1,961 sqft
- 419 greenfield road, Winter Haven 33884 $341,490 · 3 bd · 2 ba · 1,924 sqft
- 255 haines boulevard, Winter Haven 33881 $290,000 · 4 bd · 2 ba · 1,793 sqft
- 1217 michelangelo lane, Winter Haven 33884 $405,000 · 4 bd · 4 ba · 2,960 sqft
- 306 eagle pond drive, Winter Haven 33884 $211,000 · 2 bd · 2 ba · 1,017 sqft
- 352 vail drive, Winter Haven 33884 $260,000 · 3 bd · 2 ba · 2,040 sqft
- 3097 buckeye pointe drive, Winter Haven 33881 $430,000 · 5 bd · 3 ba · 2,577 sqft
- 132 duval road, Winter Haven 33884 $299,500 · 2 bd · 2 ba · 1,260 sqft
- 1716 terry circle northeast, Winter Haven 33881 $270,000 · 3 bd · 2 ba · 1,065 sqft
- 3821 avenue j northwest, Winter Haven 33881 $213,900 · 3 bd · 2 ba · 1,252 sqft
- 270 meadowbrook boulevard, Winter Haven 33881 $355,900 · 5 bd · 3 ba · 2,696 sqft
- 333 lake howard drive northwest 314d, Winter Haven 33880 $99,000 · 3 bd · 2 ba · 1,226 sqft
- 3928 giorgio drive, Winter Haven 33884 $284,150 · 4 bd · 2 ba · 1,607 sqft