Homes under $500K in Winter Garden, FL

253 for sale · 414 homes listed · Updated September 27, 2026 · Page 4 of 9

• 93 windtree lane 102, Winter Garden 34787 $199,999 · 2 bd · 2 ba · 918 sqft
• 14501 grove resort avenue 3406, Winter Garden 34787 $169,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 2119, Winter Garden 34787 $199,000 · 3 bd · 2 ba · 1,396 sqft
• 15510 campden street, Winter Garden 34787 $369,900 · 3 bd · 3 ba · 1,924 sqft
• 17802 jefferson street, Winter Garden 34787 $433,000 · 4 bd · 2 ba · 1,778 sqft
• 10108 salt point drive, Winter Garden 34787 $425,000 · 3 bd · 3 ba · 1,505 sqft
• 1668 scarlet oak loop c, Winter Garden 34787 $328,000 · 3 bd · 3 ba · 1,699 sqft
• 10607 words drive, Winter Garden 34787 $434,900 · 4 bd · 3 ba · 1,992 sqft
• 15159 groveside road, Winter Garden 34787 $494,890 · 3 bd · 3 ba · 1,881 sqft
• 7272 windy willow street, Winter Garden 34787 $483,258 · 3 bd · 3 ba · 1,697 sqft
• 7276 windy willow street, Winter Garden 34787 $456,213 · 3 bd · 3 ba · 1,764 sqft
• 14501 grove resort avenue 3401, Winter Garden 34787 $199,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 1409, Winter Garden 34787 $387,900 · 3 bd · 2 ba · 1,396 sqft
• 142 southern pecan circle 204, Winter Garden 34787 $280,500 · 3 bd · 2 ba · 1,453 sqft
• 16931 reseda alley, Winter Garden 34787 $379,990 · 3 bd · 3 ba · 1,568 sqft
• 14501 grove resort avenue 3642, Winter Garden 34787 $290,000 · 3 bd · 3 ba · 1,544 sqft
• 10660 words drive, Winter Garden 34787 $445,000 · 4 bd · 3 ba · 1,992 sqft
• 13765 golden russet drive, Winter Garden 34787 $365,000 · 3 bd · 3 ba · 1,600 sqft
• 8013 basilica lane, Winter Garden 34787 $410,000 · 3 bd · 3 ba · 1,860 sqft
• 231 east lafayette street, Winter Garden 34787 $479,900 · 4 bd · 3 ba · 1,608 sqft
• 14501 grove resort avenue 1707, Winter Garden 34787 $239,000 · 3 bd · 3 ba · 1,544 sqft
• 17723 japonica bloom drive, Winter Garden 34787 $394,999 · 3 bd · 3 ba · 1,584 sqft
• 15213 groveside road, Winter Garden 34787 $480,085 · 3 bd · 3 ba · 1,846 sqft
• 14501 grove resort avenue 2342, Winter Garden 34787 $319,000 · 3 bd · 3 ba · 1,544 sqft
• 844 klondike street, Winter Garden 34787 $199,999 · 1 bd · 1 ba · 1,300 sqft
• 15014 windflower alley, Winter Garden 34787 $424,990 · 3 bd · 3 ba · 1,536 sqft
• 16306 prairie school drive, Winter Garden 34787 $415,000 · 3 bd · 3 ba · 1,792 sqft
• 14543 golden harbor lane, Winter Garden 34787 $495,000 · 3 bd · 3 ba · 2,039 sqft
• 14501 grove resort avenue 3215, Winter Garden 34787 $199,000 · 2 bd · 2 ba · 1,265 sqft
• 16534 barbours creek way, Winter Garden 34787 $464,990 · 3 bd · 3 ba · 1,817 sqft
• 233 southern pecan circle 101, Winter Garden 34787 $229,900 · 2 bd · 1 ba · 966 sqft
• 1327 priory circle 1327, Winter Garden 34787 $368,000 · 3 bd · 3 ba · 1,650 sqft
• 14501 grove resort avenue, Winter Garden 34787 $335,000 · 3 bd · 3 ba · 1,544 sqft
• 27 windtree lane 102, Winter Garden 34787 $224,995 · 2 bd · 2 ba · 918 sqft
• 15038 windflower alley, Winter Garden 34787 $440,000 · 3 bd · 3 ba · 1,536 sqft
• 1221 priory circle, Winter Garden 34787 $380,000 · 3 bd · 3 ba · 1,675 sqft
• 13855 golden russet drive, Winter Garden 34787 $355,000 · 2 bd · 3 ba · 1,652 sqft
• 15056 windflower alley, Winter Garden 34787 $398,000 · 3 bd · 3 ba · 1,536 sqft
• 15877 tollington alley, Winter Garden 34787 $483,500 · 3 bd · 3 ba · 1,835 sqft
• 300 eron way 1, Winter Garden 34787 $224,000 · 2 bd · 2 ba · 840 sqft
• 11102 hanlon terrace alley, Winter Garden 34787 $425,000 · 3 bd · 3 ba · 1,868 sqft
• 14501 grove resort avenue 3438, Winter Garden 34787 $194,900 · 3 bd · 2 ba · 1,396 sqft
• 1422 basin street, Winter Garden 34787 $260,000 · 4 bd · 1 ba · 880 sqft
• 208 3rd street, Winter Garden 34787 $435,000 · 8 bd · 3 ba · 1,750 sqft
• 14501 grove resort avenue 3626, Winter Garden 34787 $480,000 · 3 bd · 3 ba
• 15613 orange harvest loop, Winter Garden 34787 $445,000 · 3 bd · 3 ba · 1,844 sqft
• 12086 shine view lane, Winter Garden 34787 $487,500 · 3 bd · 3 ba · 1,817 sqft
• 11202 silver trumpet loop, Winter Garden 34787 $437,993 · 2 bd · 2 ba · 1,515 sqft
• 14200 avalon road 406, Winter Garden 34787 $213,000 · 3 bd · 2 ba · 1,288 sqft
• 11199 silver trumpet loop, Winter Garden 34787 $447,118 · 2 bd · 2 ba · 1,515 sqft