5 Bedroom Homes in Winter Haven, FL

44 for sale · 100 homes listed · Updated November 9, 2026 · Page 2 of 2

• 1061 Sandpiper Loop, Winter Haven 33881 Pending $465,000 · 5 bd · 3 ba · 2,472 sqft
• 1645 Crump Road, Winter Haven 33881 Pending $1,050,000 · 5 bd · 4 ba · 3,612 sqft
• 6264 Botticella Boulevard, Winter Haven 33884 Pending $296,490 · 5 bd · 3 ba · 2,326 sqft
• 5437 San Pietro Drive, Winter Haven 33884 Pending $364,499 · 5 bd · 3 ba · 2,470 sqft
• 6276 Botticella Boulevard, Winter Haven 33884 Pending $305,490 · 5 bd · 3 ba · 2,326 sqft
• 6280 Botticella Boulevard, Winter Haven 33884 Pending $289,990 · 5 bd · 3 ba · 2,112 sqft
• 5820 Taverna Loop, Winter Haven 33884 Pending $305,990 · 5 bd · 3 ba · 2,326 sqft
• 2774 Adeline Avenue, Winter Haven 33881 Pending $294,490 · 5 bd · 2 ba · 1,708 sqft
• 5568 Taverna Loop, Winter Haven 33884 Pending $325,990 · 5 bd · 3 ba · 2,447 sqft
• 5382 San Pietro Drive, Winter Haven 33884 Pending $354,999 · 5 bd · 3 ba · 2,470 sqft
• 706 Peyton Brooke Way, Winter Haven 33881 Pending $310,000 · 5 bd · 3 ba · 2,696 sqft
• 1307 North Lake Howard Drive, Winter Haven 33881 Pending $1,250,000 · 5 bd · 4 ba · 3,300 sqft
• 6257 Botticella Boulevard, Winter Haven 33884 Pending $298,490 · 5 bd · 3 ba · 2,112 sqft
• 6217 Botticella Boulevard, Winter Haven 33884 Pending $305,490 · 5 bd · 3 ba · 2,326 sqft
• 5812 Taverna Loop, Winter Haven 33884 Pending $289,490 · 5 bd · 3 ba · 2,112 sqft
• 2795 Adeline Avenue, Winter Haven 33881 Pending $301,900 · 5 bd · 2 ba · 1,708 sqft
• 1753 Hummingbird Road, Winter Haven 33884 Pending $438,900 · 5 bd · 3 ba · 2,490 sqft
• 6260 Botticella Boulevard, Winter Haven 33884 Pending $298,990 · 5 bd · 3 ba · 2,112 sqft
• 205 Tifton Street, Winter Haven 33880 Pending $399,999 · 5 bd · 4 ba · 3,040 sqft
• 5390 San Pietro Drive, Winter Haven 33884 Pending $384,999 · 5 bd · 3 ba · 3,016 sqft
• 5441 San Pietro Drive, Winter Haven 33884 Pending $362,499 · 5 bd · 3 ba · 2,470 sqft
• 5373 San Pietro Drive, Winter Haven 33884 Pending $363,945 · 5 bd · 3 ba · 2,471 sqft
• 6245 Botticella Boulevard, Winter Haven 33884 Pending $296,990 · 5 bd · 3 ba · 2,112 sqft
• 219 Terranova Boulevard, Winter Haven 33884 Pending $428,000 · 5 bd · 3 ba · 2,549 sqft
• 3228 Country Walk Club Circle, Winter Haven 33881 Active Under Contract $349,700 · 5 bd · 3 ba · 2,616 sqft
• 1096 Sandpiper Loop, Winter Haven 33881 Active Under Contract $442,500 · 5 bd · 3 ba · 2,536 sqft
• 1396 Axel Circle, Winter Haven 33880 Active Under Contract $379,000 · 5 bd · 3 ba · 3,022 sqft
• 3749 Fieldstone Circle, Winter Haven 33881 Active Under Contract $459,990 · 5 bd · 3 ba · 2,588 sqft
• 3205 La Salle Street, Winter Haven 33884 Active Under Contract $525,000 · 5 bd · 4 ba · 3,021 sqft
• 1020 Lena Run Court, Winter Haven 33880 Active Under Contract $588,000 · 5 bd · 3 ba · 3,068 sqft
• 1436 Axel Circle, Winter Haven 33880 Active Under Contract $340,000 · 5 bd · 3 ba · 3,022 sqft
• 3935 Palazzo Place, Winter Haven 33884 Active Under Contract $225,000 · 5 bd · 3 ba · 2,601 sqft
• 1196 Lake Elbert Drive Southeast, Winter Haven 33880 Active Under Contract $449,900 · 5 bd · 3 ba · 2,242 sqft
• 306 Avenue A Wahneta East, Winter Haven 33880 Active Under Contract $174,500 · 5 bd · 2 ba · 1,747 sqft
• 605 Honey Bell Road, Winter Haven 33880 Off market since Aug 2026 $349,000 · 5 bd · 3 ba · 2,616 sqft
• 326 Meadowbrook Boulevard, Winter Haven 33881 Off market since Sep 2026 $331,995 · 5 bd · 3 ba · 2,696 sqft
• 112 Paine Drive, Winter Haven 33884 Off market since Aug 2026 $315,000 · 5 bd · 2 ba · 2,078 sqft
• 1501 7th Street Southeast, Winter Haven 33880 Off market since Jul 2026 $360,000 · 5 bd · 3 ba · 2,806 sqft
• 1392 Axel Circle, Winter Haven 33880 Off market since Jul 2026 $370,000 · 5 bd · 3 ba · 2,523 sqft
• 1783 White Elephant Loop, Winter Haven 33884 Off market since Sep 2026 $364,900 · 5 bd · 3 ba · 2,244 sqft
• 5393 San Pietro Drive, Winter Haven 33884 Off market since Sep 2026 $384,999 · 5 bd · 3 ba · 3,016 sqft
• 1018 Brimstone Circle, Winter Haven 33884 Off market since Aug 2026 $475,000 · 5 bd · 3 ba · 2,457 sqft
• 250 Brigham Road Northwest, Winter Haven 33881 Off market since Sep 2026 $1,195,000 · 5 bd · 6 ba · 3,235 sqft
• 1400 Lake Elbert Drive Southeast, Winter Haven 33884 Off market since Jul 2026 $450,000 · 5 bd · 6 ba · 3,778 sqft
• 270 Meadowbrook Boulevard, Winter Haven 33881 Off market since Sep 2026 $355,900 · 5 bd · 3 ba · 2,696 sqft
• 1302 Lake Elbert Drive Southeast, Winter Haven 33880 Off market since Sep 2026 $589,500 · 5 bd · 5 ba · 2,626 sqft
• 6272 Botticella Boulevard, Winter Haven 33884 Sold on Aug 11, 2026 $289,490 · 5 bd · 3 ba · 2,112 sqft
• 1753 Hummingbird Road, Winter Haven 33884 Off market since Sep 2026 $438,900 · 5 bd · 3 ba · 2,490 sqft
• 3831 Pomelo Drive, Winter Haven 33884 Sold on Aug 21, 2026 $350,490 · 5 bd · 3 ba · 2,077 sqft
• 5390 San Pietro Drive, Winter Haven 33884 Off market since Sep 2026 $384,999 · 5 bd · 3 ba · 3,016 sqft