Homes under $500K in Winter Haven, FL

540 for sale · 1,783 homes listed · Updated September 27, 2026 · Page 11 of 36

• 212 majestic gardens lane, Winter Haven 33880 $289,000 · 3 bd · 2 ba · 1,348 sqft
• 503 holt circle, Winter Haven 33880 $160,000 · 3 bd · 2 ba · 1,305 sqft
• 2519 avenue east southwest, Winter Haven 33880 $299,900 · 3 bd · 2 ba · 1,675 sqft
• 1727 second street northeast, Winter Haven 33881 $260,000 · 3 bd · 2 ba · 1,470 sqft
• 5351 mickey avenue, Winter Haven 33884 $309,999 · 3 bd · 2 ba · 1,700 sqft
• 624 sarner pass way, Winter Haven 33881 $299,000 · 4 bd · 2 ba · 1,617 sqft
• 1100 martinique drive #220, Winter Haven 33884 $149,900 · 3 bd · 2 ba · 1,806 sqft
• 306 avenue a wahneta east, Winter Haven 33880 $174,500 · 5 bd · 2 ba · 1,747 sqft
• 3927 palazzo place, Winter Haven 33884 $300,000 · 3 bd · 2 ba · 1,597 sqft
• 3097 buckeye pointe drive, Winter Haven 33881 $430,000 · 5 bd · 3 ba · 2,577 sqft
• 5444 san pietro drive, Winter Haven 33884 $314,999 · 4 bd · 3 ba · 2,226 sqft
• 5386 san pietro drive, Winter Haven 33884 $324,999 · 4 bd · 3 ba · 2,226 sqft
• 5377 san pietro drive, Winter Haven 33884 $309,999 · 4 bd · 3 ba · 2,039 sqft
• 5445 san pietro drive, Winter Haven 33884 $319,999 · 4 bd · 3 ba · 2,039 sqft
• 5449 san pietro drive, Winter Haven 33884 $309,999 · 4 bd · 3 ba · 2,039 sqft
• 551 lake smart boulevard, Winter Haven 33881 $334,900 · 4 bd · 2 ba · 1,936 sqft
• 3948 giorgio drive, Winter Haven 33884 $259,900 · 3 bd · 2 ba · 1,483 sqft
• 1205 eagle pond drive #1205, Winter Haven 33884 $162,000 · 2 bd · 2 ba · 1,017 sqft
• 113 6th jpv street, Winter Haven 33880 $249,000 · 3 bd · 2 ba · 1,035 sqft
• 2011 recker highway, Winter Haven 33880 $390,000 · 4 bd · 2 ba · 2,000 sqft
• 3018 royal tern drive, Winter Haven 33881 $269,900 · 3 bd · 2 ba · 1,690 sqft
• 751 grove street, Winter Haven 33881 $329,999 · 4 bd · 2 ba · 1,867 sqft
• 2216 starboard, Winter Haven 33881 $215,000 · 3 bd · 3 ba · 1,549 sqft
• 1787 white elephant loop, Winter Haven 33884 $279,900 · 3 bd · 2 ba · 1,526 sqft
• 6827 south lake henry drive northeast, Winter Haven 33881 $195,000 · 4 bd · 2 ba · 1,450 sqft
• 2820 traditions boulevard south, Winter Haven 33884 $309,900 · 3 bd · 2 ba · 1,823 sqft
• 210 meadowbrook boulevard, Winter Haven 33881 $380,000 · 5 bd · 3 ba · 2,696 sqft
• 525 squires grove drive, Winter Haven 33880 $290,000 · 4 bd · 2 ba · 1,872 sqft
• 489 village circle southwest, Winter Haven 33880 $150,000 · 2 bd · 2 ba · 1,008 sqft
• 419 avenue m northeast, Winter Haven 33881 $244,999 · 3 bd · 2 ba · 1,232 sqft
• 3614 plymouth drive, Winter Haven 33884 $310,000 · 3 bd · 2 ba · 2,109 sqft
• 0 38th street northwest, Winter Haven 33881 $350,000 · 3 bd · 2 ba · 1,322 sqft
• 1525 oakview circle southeast, Winter Haven 33880 $199,000 · 2 bd · 2 ba · 1,333 sqft
• 271 mariposa, Winter Haven 33884 $249,000 · 3 bd · 2 ba · 1,571 sqft
• 3035 buckeye pointe drive, Winter Haven 33881 $369,900 · 4 bd · 3 ba · 2,070 sqft
• 948 summer glen drive, Winter Haven 33880 $259,990 · 3 bd · 2 ba · 1,690 sqft
• 1631 linz court, Winter Haven 33884 $190,500 · 2 bd · 2 ba · 1,231 sqft
• 4064 phoenician way, Winter Haven 33884 $449,900 · 3 bd · 2 ba · 2,354 sqft
• 7002 summit circle, Winter Haven 33884 $340,000 · 3 bd · 2 ba · 1,888 sqft
• 7808 waterview way, Winter Haven 33884 $115,000 · 2 bd · 2 ba · 559 sqft
• 700 mirror terrace northwest 303, Winter Haven 33881 Pending $99,900 · 2 bd · 2 ba · 1,029 sqft
• 17 kendra court, Winter Haven 33880 Pending $110,000 · 2 bd · 2 ba · 960 sqft
• 2335 brassie court, Winter Haven 33884 Pending $295,529 · 4 bd · 3 ba · 2,202 sqft
• 6056 navona way, Winter Haven 33884 Pending $259,999 · 3 bd · 2 ba · 1,615 sqft
• 35 south lake fox road, Winter Haven 33884 Pending $399,999 · 3 bd · 3 ba · 2,149 sqft
• 1228 denali drive, Winter Haven 33881 Pending $295,900 · 4 bd · 2 ba · 1,707 sqft
• 241 grove branch road, Winter Haven 33880 Pending $224,900 · 3 bd · 2 ba · 1,140 sqft
• 1516 avenue d northeast, Winter Haven 33881 Pending $270,000 · 3 bd · 2 ba · 1,089 sqft
• 29 golf view circle northeast, Winter Haven 33881 Pending $250,000 · 3 bd · 2 ba · 1,604 sqft
• 2787 adeline avenue, Winter Haven 33881 Pending $268,900 · 3 bd · 2 ba · 1,328 sqft