5 Bedroom Homes in Winter Garden, FL

74 for sale · 288 homes listed · Updated September 27, 2026 · Page 5 of 6

• 5973 cypress hill road, Winter Garden 34787 Off market since Sep 2026 $694,000 · 5 bd · 4 ba · 3,532 sqft
• 6100 cypress hill road, Winter Garden 34787 Off market since Sep 2026 $799,000 · 5 bd · 3 ba · 3,777 sqft
• 3362 hanging tide street, Winter Garden 34787 Off market since Aug 2026 $875,000 · 5 bd · 5 ba · 4,495 sqft
• 14102 lochend way, Winter Garden 34787 Off market since Aug 2026 $935,000 · 5 bd · 5 ba · 3,606 sqft
• 15652 gentle rain drive, Winter Garden 34787 Off market since Sep 2026 $839,000 · 5 bd · 5 ba · 3,657 sqft
• 8768 sonoma coast drive, Winter Garden 34787 Off market since Sep 2026 $890,000 · 5 bd · 5 ba · 3,416 sqft
• 7687 bowery drive, Winter Garden 34787 Off market since Sep 2026 $790,000 · 5 bd · 4 ba · 3,179 sqft
• 13856 glynshel drive, Winter Garden 34787 Off market since Sep 2026 $860,000 · 5 bd · 4 ba · 3,538 sqft
• 13086 sunrise harvest drive, Winter Garden 34787 Off market since Sep 2026 $799,000 · 5 bd · 4 ba · 2,835 sqft
• 15741 sweet lemon way, Winter Garden 34787 Off market since Sep 2026 $1,099,000 · 5 bd · 5 ba · 3,624 sqft
• 13129 faro court, Winter Garden 34787 Off market since Sep 2026 $779,000 · 5 bd · 5 ba · 3,664 sqft
• 8750 bayview crossing drive, Winter Garden 34787 Off market since Sep 2026 $1,724,500 · 5 bd · 6 ba · 4,641 sqft
• 9929 summerlake groves street, Winter Garden 34787 Sold on Jul 16, 2026 $899,990 · 5 bd · 5 ba · 4,034 sqft
• 14312 sunbridge circle, Winter Garden 34787 Off market since Sep 2026 $1,060,000 · 5 bd · 4 ba · 4,225 sqft
• 552 egret place drive, Winter Garden 34787 Off market since Sep 2026 $699,900 · 5 bd · 3 ba · 3,395 sqft
• 14741 snowy egret street, Winter Garden 34787 Off market since Sep 2026 $725,000 · 5 bd · 4 ba · 3,448 sqft
• 11827 shine view lane, Winter Garden 34787 Off market since Sep 2026 $863,626 · 5 bd · 5 ba · 3,225 sqft
• 11821 shine view lane, Winter Garden 34787 Off market since Sep 2026 $840,000 · 5 bd · 4 ba · 2,866 sqft
• 2106 black lake boulevard, Winter Garden 34787 Off market since Jul 2026 $980,000 · 5 bd · 4 ba · 4,111 sqft
• 14301 white moss way, Winter Garden 34787 Off market since Sep 2026 $899,999 · 5 bd · 4 ba · 4,053 sqft
• 1642 chandelle lane, Winter Garden 34787 Off market since Sep 2026 $669,900 · 5 bd · 3 ba · 2,918 sqft
• 1711 amsel falls park terrace, Winter Garden 34787 Off market since Sep 2026 $1,046,000 · 5 bd · 4 ba · 3,863 sqft
• 844 oakland park boulevard, Winter Garden 34787 Off market since Sep 2026 $1,195,000 · 5 bd · 4 ba · 3,525 sqft
• 16044 citrus knoll drive, Winter Garden 34787 Off market since Sep 2026 $1,020,000 · 5 bd · 4 ba · 3,617 sqft
• 15026 summer harvest street, Winter Garden 34787 Off market since Sep 2026 $629,990 · 5 bd · 5 ba · 2,930 sqft
• 15031 guava bay drive, Winter Garden 34787 Off market since Sep 2026 $890,000 · 5 bd · 5 ba · 3,958 sqft
• 2010 boss hewett street, Winter Garden 34787 Off market since Sep 2026 $1,500,000 · 5 bd · 4 ba · 3,781 sqft
• 11863 shine view lane, Winter Garden 34787 Off market since Sep 2026 $850,621 · 5 bd · 4 ba · 2,866 sqft
• 8060 bowery drive, Winter Garden 34787 Off market since Sep 2026 $599,900 · 5 bd · 3 ba · 3,013 sqft
• 12706 grovehurst avenue, Winter Garden 34787 Off market since Sep 2026 $590,000 · 5 bd · 3 ba · 3,382 sqft
• 5079 palmetto park drive, Winter Garden 34787 Off market since Sep 2026 $910,000 · 5 bd · 4 ba · 3,866 sqft
• 15784 sweet limetta drive, Winter Garden 34787 Off market since Sep 2026 $850,000 · 5 bd · 5 ba · 3,635 sqft
• 11869 shine view lane, Winter Garden 34787 Off market since Sep 2026 $887,066 · 5 bd · 5 ba · 3,225 sqft
• 15512 fountain cove court, Winter Garden 34787 Off market since Sep 2026 $725,000 · 5 bd · 4 ba · 3,227 sqft
• 5320 lake virginia street, Winter Garden 34787 Off market since Sep 2026 $695,990 · 5 bd · 4 ba · 3,366 sqft
• 13163 lakeshore grove drive, Winter Garden 34787 Off market since Aug 2026 $759,900 · 5 bd · 3 ba · 3,249 sqft
• 706 strihal loop, Winter Garden 34787 Off market since Sep 2026 $569,000 · 5 bd · 4 ba · 3,020 sqft
• 14779 mcclane road, Winter Garden 34787 Off market since Sep 2026 $899,000 · 5 bd · 4 ba · 3,118 sqft
• 15068 lebeau loop, Winter Garden 34787 Off market since Sep 2026 $644,000 · 5 bd · 4 ba · 3,266 sqft
• 15367 shonan gold drive, Winter Garden 34787 Off market since Sep 2026 $899,000 · 5 bd · 5 ba · 3,002 sqft
• 16038 johns lake overlook drive, Winter Garden 34787 Off market since Sep 2026 $2,099,000 · 5 bd · 5 ba · 4,139 sqft
• 9225 holliston creek place, Winter Garden 34787 Off market since Sep 2026 $1,150,000 · 5 bd · 4 ba · 3,897 sqft
• 637 grassy stone drive, Winter Garden 34787 Off market since Sep 2026 $800,000 · 5 bd · 3 ba · 3,241 sqft
• 1734 amsel falls park terrace, Winter Garden 34787 Off market since Sep 2026 $1,249,990 · 5 bd · 5 ba · 4,305 sqft
• 16124 azure key street, Winter Garden 34787 Off market since Sep 2026 $765,000 · 5 bd · 4 ba · 2,840 sqft
• 2450 dahlgren way, Winter Garden 34787 Off market since Aug 2026 $1,625,000 · 5 bd · 5 ba · 4,365 sqft
• 16394 taliesin street, Winter Garden 34787 Off market since Sep 2026 $890,000 · 5 bd · 5 ba · 3,093 sqft
• 1664 holcomb creek street, Winter Garden 34787 Off market since Sep 2026 $1,080,000 · 5 bd · 5 ba · 4,305 sqft
• 16091 silver brook way, Winter Garden 34787 Off market since Sep 2026 $1,100,000 · 5 bd · 5 ba · 3,743 sqft
• 17338 wild daisy drive, Winter Garden 34787 Off market since Sep 2026 $798,990 · 5 bd · 4 ba · 3,076 sqft