Homes over $1M in Winter Garden, FL

40 for sale · 186 homes listed · Updated September 27, 2026 · Page 1 of 4

• 15499 shorebird lane, Winter Garden 34787 $2,380,000 · 4 bd · 6 ba
• 906 allendale lane, Winter Garden 34787 $1,725,000 · 5 bd · 4 ba · 3,784 sqft
• 1664 holcomb creek street, Winter Garden 34787 $1,080,000 · 5 bd · 5 ba · 4,305 sqft
• 16077 barkly ridge court, Winter Garden 34787 $1,999,000 · 6 bd · 7 ba · 5,248 sqft
• 650 medora way, Winter Garden 34787 $1,157,190 · 4 bd · 3 ba · 2,902 sqft
• 16038 johns lake overlook drive, Winter Garden 34787 $2,099,000 · 5 bd · 5 ba · 4,139 sqft
• 16071 barkly ridge court, Winter Garden 34787 $1,150,000 · 4 bd · 3 ba · 2,986 sqft
• 9225 holliston creek place, Winter Garden 34787 $1,150,000 · 5 bd · 4 ba · 3,897 sqft
• 14312 sunbridge circle, Winter Garden 34787 $1,060,000 · 5 bd · 4 ba · 4,225 sqft
• 9056 morgana court, Winter Garden 34787 $2,050,000 · 5 bd · 5 ba · 4,832 sqft
• 9207 busaco park way, Winter Garden 34787 $1,000,000 · 5 bd · 4 ba · 3,291 sqft
• 925 easley avenue, Winter Garden 34787 $1,125,000 · 4 bd · 4 ba · 2,667 sqft
• 9103 morgana court, Winter Garden 34787 $1,339,000 · 5 bd · 5 ba · 4,376 sqft
• 4708 weatherbell road, Winter Garden 34787 $1,089,000 · 4 bd · 5 ba · 3,562 sqft
• 4817 fair winds court, Winter Garden 34787 $1,200,000 · 5 bd · 5 ba · 4,396 sqft
• 17854 hither hills circle, Winter Garden 34787 $1,100,000 · 4 bd · 3 ba · 2,929 sqft
• 1101 eagles pass way, Winter Garden 34787 $1,644,999 · 6 bd · 5 ba · 4,104 sqft
• 15522 shorebird lane, Winter Garden 34787 $2,700,000 · 7 bd · 7 ba · 6,400 sqft
• 15625 sylvester palm drive, Winter Garden 34787 $1,085,000 · 5 bd · 5 ba · 3,886 sqft
• 9110 morgana court, Winter Garden 34787 $1,999,000 · 5 bd · 5 ba · 4,661 sqft
• 7693 green mountain way, Winter Garden 34787 $2,600,000 · 6 bd · 6 ba · 5,115 sqft
• 8222 topsail place, Winter Garden 34787 $1,170,000 · 5 bd · 5 ba · 4,199 sqft
• 72 north park avenue #8, Winter Garden 34787 $1,149,000 · 3 bd · 4 ba · 2,040 sqft
• 205 surprise drive, Winter Garden 34787 $1,200,000 · 4 bd · 3 ba · 2,171 sqft
• 13377 lake butler boulevard, Winter Garden 34787 $2,500,000 · 4 bd · 5 ba · 4,961 sqft
• 5074 breezy acres street, Winter Garden 34787 $1,159,900 · 7 bd · 5 ba · 4,720 sqft
• 14048 larkspur lake drive, Winter Garden 34787 $1,295,000 · 4 bd · 3 ba · 2,464 sqft
• 16044 citrus knoll drive, Winter Garden 34787 $1,020,000 · 5 bd · 4 ba · 3,617 sqft
• 9845 emerald berry drive, Winter Garden 34787 $1,090,000 · 5 bd · 5 ba · 3,878 sqft
• 8750 bayview crossing drive, Winter Garden 34787 $1,724,500 · 5 bd · 6 ba · 4,641 sqft
• 3208 sailing pier avenue, Winter Garden 34787 $1,000,000 · 5 bd · 4 ba · 3,998 sqft
• 243 zachary wade street, Winter Garden 34787 $1,220,000 · 5 bd · 4 ba · 3,097 sqft
• 15210 east oakland avenue, Winter Garden 34787 $1,924,999 · 4 bd · 3 ba · 3,789 sqft
• 17372 glossy pomelo way, Winter Garden 34787 $1,629,900 · 5 bd · 6 ba · 4,977 sqft
• 16788 muskgrass drive, Winter Garden 34787 $1,550,000 · 4 bd · 5 ba · 4,733 sqft
• 2010 boss hewett street, Winter Garden 34787 $1,500,000 · 5 bd · 4 ba · 3,781 sqft
• 844 oakland park boulevard, Winter Garden 34787 $1,195,000 · 5 bd · 4 ba · 3,525 sqft
• 1032 galston alley, Winter Garden 34787 $1,650,000 · 5 bd · 5 ba · 3,506 sqft
• 16091 silver brook way, Winter Garden 34787 $1,100,000 · 5 bd · 5 ba · 3,743 sqft
• 907 celadon street, Winter Garden 34787 $2,495,000 · 6 bd · 6 ba · 5,036 sqft
• 13217 tollcross way, Winter Garden 34787 Pending $1,249,000 · 6 bd · 5 ba · 4,152 sqft
• 15686 panther lake drive, Winter Garden 34787 Pending $1,190,000 · 4 bd · 5 ba · 3,094 sqft
• 16006 gilden way, Winter Garden 34787 Pending $1,024,999 · 5 bd · 4 ba · 3,617 sqft
• 217 west bay street, Winter Garden 34787 Pending $1,295,000 · 5 bd · 4 ba · 2,800 sqft
• 14240 colonial pointe drive, Winter Garden 34787 Pending $1,250,000 · 6 bd · 6 ba · 4,816 sqft
• 8530 bayview crossing drive, Winter Garden 34787 Pending $1,299,000 · 4 bd · 4 ba · 4,130 sqft
• 15138 shonan gold drive, Winter Garden 34787 Pending $2,799,950 · 5 bd · 7 ba · 5,551 sqft
• 10198 merrymeeting bay drive, Winter Garden 34787 Pending $1,160,000 · 5 bd · 4 ba · 3,911 sqft
• 7467 john hancock drive, Winter Garden 34787 Pending $1,350,000 · 4 bd · 4 ba · 3,964 sqft
• 1324 vic kay court, Winter Garden 34787 Pending $1,390,000 · 5 bd · 4 ba · 3,749 sqft