Homes under $300K in Winter Haven, FL

333 for sale · 1,131 homes listed · Updated September 27, 2026 · Page 10 of 23

• 4040 giorgio, Winter Haven 33884 Pending $287,990 · 3 bd · 2 ba · 1,672 sqft
• 1040 luke avenue, Winter Haven 33881 Pending $269,990 · 3 bd · 2 ba · 1,407 sqft
• 6163 coronari lane, Winter Haven 33884 Pending $283,490 · 3 bd · 2 ba · 1,504 sqft
• 4811 khloe court, Winter Haven 33884 Pending $281,900 · 3 bd · 2 ba · 1,504 sqft
• 3740 giorgio drive, Winter Haven 33884 Pending $292,900 · 3 bd · 2 ba · 1,672 sqft
• 820 water oaks drive, Winter Haven 33880 Pending $89,500 · 3 bd · 2 ba · 1,248 sqft
• 3968 giorgio drive, Winter Haven 33884 Pending $270,000 · 3 bd · 2 ba · 1,269 sqft
• 319 avenue a northeast, Winter Haven 33881 Pending $265,000 · 3 bd · 2 ba · 1,560 sqft
• 108 9th eloise street, Winter Haven 33880 Pending $95,000 · 3 bd · 1 ba · 1,080 sqft
• 251 caleb way, Winter Haven 33881 Pending $280,000 · 4 bd · 2 ba · 1,852 sqft
• 4063 rolling oaks drive, Winter Haven 33880 Pending $114,995 · 2 bd · 2 ba · 1,320 sqft
• 133 rebecca drive northeast, Winter Haven 33881 Pending $299,000 · 3 bd · 2 ba · 1,342 sqft
• 3021 captain jax way, Winter Haven 33884 Pending $219,990 · 3 bd · 3 ba · 1,386 sqft
• 212 avenue f southeast, Winter Haven 33880 Pending $69,900 · 1 bd · 1 ba · 800 sqft
• 2007 garden lake drive 2007, Winter Haven 33884 Pending $178,500 · 2 bd · 2 ba · 1,103 sqft
• 1825 16th street northwest, Winter Haven 33881 Pending $99,900 · 2 bd · 2 ba · 1,395 sqft
• 432 savanna pointe street, Winter Haven 33884 Pending $269,900 · 3 bd · 2 ba · 1,867 sqft
• 3004 sunset hills road, Winter Haven 33881 Pending $299,990 · 3 bd · 2 ba · 1,536 sqft
• 6257 botticella boulevard, Winter Haven 33884 Pending $298,490 · 5 bd · 3 ba · 2,112 sqft
• 3947 warbler drive, Winter Haven 33880 Pending $274,999 · 3 bd · 2 ba · 1,632 sqft
• 3067 captain jax way, Winter Haven 33884 Pending $220,240 · 3 bd · 3 ba · 1,386 sqft
• 6260 botticella boulevard, Winter Haven 33884 Pending $293,990 · 5 bd · 3 ba · 2,112 sqft
• 1114 carefree cove drive, Winter Haven 33881 Pending $165,000 · 3 bd · 2 ba · 1,300 sqft
• 3087 captain jax way, Winter Haven 33884 Pending $224,990 · 3 bd · 3 ba · 1,386 sqft
• 6308 bayberry boulevard northeast, Winter Haven 33881 Active Under Contract $155,700 · 2 bd · 2 ba · 1,152 sqft
• 104 avenue k avenue northeast, Winter Haven 33881 Active Under Contract $200,000 · 3 bd · 1 ba · 1,190 sqft
• 1109 5th street southwest, Winter Haven 33880 Active Under Contract $195,000 · 3 bd · 2 ba · 1,238 sqft
• 880 oleander drive southeast, Winter Haven 33880 Active Under Contract $289,000 · 3 bd · 2 ba · 2,172 sqft
• 4127 sprucewood street, Winter Haven 33880 Active Under Contract $85,000 · 2 bd · 2 ba · 1,035 sqft
• 6346 bayberry boulevard northeast, Winter Haven 33881 Active Under Contract $189,900 · 3 bd · 2 ba · 1,440 sqft
• 1150 high seas street, Winter Haven 33880 Active Under Contract $270,600 · 3 bd · 2 ba · 1,702 sqft
• 871 reflections loop east, Winter Haven 33884 Active Under Contract $213,000 · 3 bd · 2 ba · 1,264 sqft
• 2202 garden lake drive, Winter Haven 33884 Active Under Contract $249,000 · 3 bd · 2 ba · 1,442 sqft
• 6644 princeton drive northeast, Winter Haven 33881 Active Under Contract $129,900 · 2 bd · 2 ba · 1,296 sqft
• 1108 brenton manor drive, Winter Haven 33881 Active Under Contract $285,000 · 3 bd · 2 ba · 1,584 sqft
• 414 avenue c avenue northeast, Winter Haven 33881 Active Under Contract $214,999 · 2 bd · 2 ba · 1,140 sqft
• 345 24th street northwest 25, Winter Haven 33880 Active Under Contract $120,000 · 2 bd · 2 ba · 1,008 sqft
• 250 volusia drive, Winter Haven 33884 Active Under Contract $259,000 · 3 bd · 2 ba · 1,449 sqft
• 113 citrus drive, Winter Haven 33884 Active Under Contract $259,000 · 3 bd · 2 ba · 2,016 sqft
• 6518 crescent loop, Winter Haven 33884 Active Under Contract $230,000 · 3 bd · 2 ba · 1,894 sqft
• 4410 limewood street, Winter Haven 33880 Active Under Contract $110,000 · 2 bd · 2 ba · 1,152 sqft
• 3363 livingston way, Winter Haven 33884 Active Under Contract $235,000 · 2 bd · 2 ba · 1,118 sqft
• 345 24th street northwest 23, Winter Haven 33880 Active Under Contract $170,000 · 2 bd · 2 ba · 942 sqft
• 120 4th wahneta street east, Winter Haven 33880 Active Under Contract $150,000 · 3 bd · 2 ba · 864 sqft
• 1374 benevento drive, Winter Haven 33884 Active Under Contract $199,900 · 4 bd · 2 ba · 1,849 sqft
• 404 country lane northeast 404, Winter Haven 33881 Active Under Contract $80,000 · 2 bd · 2 ba · 1,252 sqft
• 3098 laurel oak lane, Winter Haven 33884 Active Under Contract $185,000 · 3 bd · 2 ba · 1,978 sqft
• 104 11th street southeast, Winter Haven 33880 Active Under Contract $267,500 · 3 bd · 3 ba · 1,792 sqft
• 6561 chinaberry drive northeast, Winter Haven 33881 Active Under Contract $155,900 · 2 bd · 2 ba · 1,596 sqft
• 15 lake howard drive northwest, Winter Haven 33880 Active Under Contract $240,000 · 6 bd · 4 ba · 2,883 sqft