Homes under $1M in Winter Haven, FL

572 for sale · 1,886 homes listed · Updated September 27, 2026 · Page 20 of 38

• 3722 fieldstone circle, Winter Haven 33881 Active Under Contract $298,900 · 4 bd · 2 ba · 1,835 sqft
• 5872 red fox drive, Winter Haven 33884 Active Under Contract $175,000 · 3 bd · 2 ba · 1,344 sqft
• 308 hernando road, Winter Haven 33884 Active Under Contract $475,000 · 3 bd · 2 ba · 2,050 sqft
• 1668 roselawn street southwest, Winter Haven 33880 Active Under Contract $219,900 · 3 bd · 1 ba · 1,100 sqft
• 3729 fieldstone circle, Winter Haven 33881 Active Under Contract $290,000 · 4 bd · 2 ba · 1,797 sqft
• 136 whitman road, Winter Haven 33884 Active Under Contract $239,500 · 3 bd · 2 ba · 1,319 sqft
• 288 cherry laurel lane, Winter Haven 33880 Active Under Contract $235,000 · 3 bd · 2 ba · 1,276 sqft
• 1505 lake thomas loop, Winter Haven 33880 Active Under Contract $335,000 · 3 bd · 2 ba · 2,116 sqft
• 5016 river lake road, Winter Haven 33884 Active Under Contract $410,000 · 3 bd · 2 ba · 2,350 sqft
• 209 avenue c northeast, Winter Haven 33881 Active Under Contract $180,000 · 3 bd · 2 ba · 1,000 sqft
• 121 lowell road, Winter Haven 33884 Active Under Contract $335,000 · 3 bd · 2 ba · 1,980 sqft
• 120 lake mariam way, Winter Haven 33884 Active Under Contract $415,000 · 4 bd · 3 ba · 2,308 sqft
• 4112 sprucewood street, Winter Haven 33880 Active Under Contract $119,900 · 2 bd · 2 ba · 912 sqft
• 806 avenue l southeast, Winter Haven 33880 Active Under Contract $219,900 · 3 bd · 2 ba · 1,397 sqft
• 1429 lucerne loop road northeast, Winter Haven 33881 Active Under Contract $259,000 · 4 bd · 2 ba · 1,746 sqft
• 5850 cypress gardens boulevard 304, Winter Haven 33884 Off market since Sep 2026 $139,000 · 2 bd · 2 ba · 1,332 sqft
• 508 lakeside ranch way, Winter Haven 33881 Off market since Sep 2026 $79,000 · 2 bd · 2 ba · 1,128 sqft
• 1004 avenue g northeast, Winter Haven 33881 Off market since Aug 2026 $310,000 · 3 bd · 2 ba · 1,398 sqft
• 1540 avenue c northeast, Winter Haven 33881 Off market since Jul 2026 $245,000 · 3 bd · 2 ba · 1,344 sqft
• 821 sun burst road, Winter Haven 33880 Off market since Sep 2026 $360,000 · 5 bd · 3 ba · 2,601 sqft
• 104 woden way, Winter Haven 33884 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 2,218 sqft
• 100 lakeside ranch drive, Winter Haven 33881 Off market since Sep 2026 $120,000 · 2 bd · 2 ba · 1,176 sqft
• 1561 vienna square drive, Winter Haven 33884 Off market since Sep 2026 $225,000 · 2 bd · 2 ba · 1,231 sqft
• 1787 white elephant loop, Winter Haven 33884 Off market since Sep 2026 $279,900 · 3 bd · 2 ba · 1,526 sqft
• 441 san jose drive, Winter Haven 33884 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,843 sqft
• 503 holt circle, Winter Haven 33880 Off market since Sep 2026 $160,000 · 3 bd · 2 ba · 1,305 sqft
• 6107 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $179,900 · 2 bd · 2 ba · 1,340 sqft
• 4321 cherrywood street, Winter Haven 33880 Off market since Sep 2026 $108,000 · 2 bd · 2 ba · 1,488 sqft
• 6044 grand oaks drive southeast, Winter Haven 33884 Off market since Sep 2026 $145,000 · 2 bd · 2 ba · 1,248 sqft
• 689 lake howard drive northwest 1e, Winter Haven 33880 Off market since Sep 2026 $124,000 · 2 bd · 2 ba · 1,050 sqft
• 235 hibiscus street, Winter Haven 33881 Off market since Sep 2026 $274,400 · 5 bd · 3 ba · 2,527 sqft
• 123 osprey heights drive, Winter Haven 33880 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,329 sqft
• 683 broadmoor circle 683, Winter Haven 33884 Off market since Sep 2026 $193,000 · 2 bd · 2 ba · 1,139 sqft
• 2218 abbey road, Winter Haven 33880 Off market since Sep 2026 $179,999 · 2 bd · 2 ba · 1,252 sqft
• 1703 linz court, Winter Haven 33884 Off market since Sep 2026 $248,000 · 2 bd · 2 ba · 1,164 sqft
• 4099 island lakes drive, Winter Haven 33881 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 1,603 sqft
• 126 bermuda court, Winter Haven 33880 Off market since Jul 2026 $325,000 · 4 bd · 2 ba · 2,052 sqft
• 1224 vienna square drive, Winter Haven 33884 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,118 sqft
• 3206 heron cove, Winter Haven 33884 Sold on Sep 9, 2026 $579,900 · 3 bd · 3 ba · 3,050 sqft
• 3931 avenue r northwest, Winter Haven 33881 Off market since Sep 2026 $185,000 · 3 bd · 2 ba · 928 sqft
• 912 avenue t southeast, Winter Haven 33880 Off market since Aug 2026 $295,000 · 3 bd · 2 ba · 2,149 sqft
• 215 10th wahneta street west, Winter Haven 33880 Off market since Sep 2026 $145,061 · 3 bd · 2 ba · 800 sqft
• 5135 kinsley drive, Winter Haven 33884 Off market since Sep 2026 $319,950 · 4 bd · 2 ba · 1,919 sqft
• 5147 kinsley drive, Winter Haven 33884 Off market since Sep 2026 $324,999 · 4 bd · 2 ba · 1,919 sqft
• 119 allen avenue, Winter Haven 33880 Off market since Sep 2026 $219,000 · 4 bd · 2 ba · 1,520 sqft
• 621 vittorio drive, Winter Haven 33884 Off market since Sep 2026 $305,000 · 4 bd · 2 ba · 1,857 sqft
• 3132 country club circle, Winter Haven 33881 Off market since Sep 2026 $314,900 · 4 bd · 2 ba · 1,851 sqft
• 1700 6th street northwest a38, Winter Haven 33881 Off market since Jul 2026 $79,800 · 2 bd · 1 ba · 840 sqft
• 4246 cedarwood street, Winter Haven 33880 Off market since Sep 2026 $99,000 · 2 bd · 2 ba · 1,008 sqft
• 5163 kinsley drive, Winter Haven 33884 Off market since Sep 2026 $339,999 · 4 bd · 3 ba · 2,077 sqft