Homes under $500K in Winter Garden, FL

221 for sale · 576 homes listed · Updated November 9, 2026 · Page 2 of 12

• 14501 Grove Resort Avenue #2221, Winter Garden 34787 $184,900 · 2 bd · 2 ba · 1,375 sqft
• Listing-10668757208, Winter Garden 34787 $212,000 · 1 bd · 1 ba · 942 sqft
• 14501 Grove Resort Avenue #2342, Winter Garden 34787 $319,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 Grove Resort Avenue #1114, Winter Garden 34787 $239,500 · 3 bd · 3 ba · 1,544 sqft
• 14501 Grove Resort Avenue #1721, Winter Garden 34787 $220,000 · 3 bd · 2 ba · 1,396 sqft
• 12792 Sunset Walk Drive, Winter Garden 34787 $499,000 · 4 bd · 3 ba · 1,930 sqft
• 15101 Purple Martin Street, Winter Garden 34787 $489,900 · 3 bd · 3 ba · 1,998 sqft
• 431 Southern Pecan Circle #101, Winter Garden 34787 $274,500 · 3 bd · 2 ba · 1,340 sqft
• 14501 Grove Resort Avenue #1732, Winter Garden 34787 $159,950 · 2 bd · 2 ba · 1,265 sqft
• 14501 Grove Resort Avenue #3429, Winter Garden 34787 $298,900 · 3 bd · 2 ba · 1,396 sqft
• 8019 Jeremy Joseph Alley, Winter Garden 34787 $389,900 · 3 bd · 3 ba · 1,696 sqft
• 15038 Windflower Alley, Winter Garden 34787 $440,000 · 3 bd · 3 ba · 1,536 sqft
• 420 East Cypress Street, Winter Garden 34787 $400,000 · 3 bd · 2 ba · 1,616 sqft
• 10648 Words Drive, Winter Garden 34787 $409,999 · 3 bd · 3 ba · 1,636 sqft
• 300 Eron Way #1, Winter Garden 34787 $254,000 · 2 bd · 2 ba · 840 sqft
• 14501 Grove Resort Avenue #3135, Winter Garden 34787 $250,000 · 2 bd · 2 ba · 1,434 sqft
• 9467 Cinzel Alley, Winter Garden 34787 $455,000 · 3 bd · 3 ba · 1,814 sqft
• 9362 Woodcrane Drive, Winter Garden 34787 $435,800 · 3 bd · 3 ba · 2,058 sqft
• 14501 Grove Resort Avenue #2528, Winter Garden 34787 $199,000 · 3 bd · 3 ba · 1,544 sqft
• 11367 Great Rock Street, Winter Garden 34787 $430,000 · 3 bd · 3 ba · 1,717 sqft
• 14501 Grove Resort Avenue #2527, Winter Garden 34787 $215,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 Grove Resort Avenue #3201, Winter Garden 34787 $245,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 Grove Resort Avenue #3701, Winter Garden 34787 $335,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 Grove Resort Avenue #2608, Winter Garden 34787 $255,000 · 3 bd · 2 ba · 1,396 sqft
• 14766 Peekskill Drive, Winter Garden 34787 $332,500 · 2 bd · 3 ba · 1,406 sqft
• 14501 Grove Resort Avenue #1705, Winter Garden 34787 $185,000 · 2 bd · 2 ba · 1,265 sqft
• 5751 New Independence Parkway, Winter Garden 34787 $389,000 · 2 bd · 3 ba · 1,540 sqft
• 483 Pennsylvania Avenue, Winter Garden 34787 $334,000 · 2 bd · 2 ba · 1,008 sqft
• 1112 Juniper Hammock Court, Winter Garden 34787 $485,000 · 4 bd · 2 ba · 2,545 sqft
• 6208 Aralia Ivy Lane, Winter Garden 34787 $375,000 · 3 bd · 3 ba · 1,560 sqft
• 14543 Golden Harbor Lane, Winter Garden 34787 $485,000 · 3 bd · 3 ba · 2,039 sqft
• 16306 Prairie School Drive, Winter Garden 34787 $389,900 · 3 bd · 3 ba · 1,792 sqft
• 397 Eron Way #42, Winter Garden 34787 $199,999 · 3 bd · 2 ba · 930 sqft
• 15075 Groveside Road, Winter Garden 34787 $489,990 · 3 bd · 3 ba · 1,881 sqft
• 14501 Grove Resort Avenue #1527, Winter Garden 34787 $170,000 · 2 bd · 2 ba · 1,265 sqft
• 14014 Scarlet Aster Alley, Winter Garden 34787 $445,000 · 3 bd · 3 ba · 1,808 sqft
• 6982 Twilight Bay Drive, Winter Garden 34787 $470,000 · 4 bd · 3 ba · 1,860 sqft
• 93 Windtree Lane #102, Winter Garden 34787 $188,000 · 2 bd · 2 ba · 918 sqft
• 14501 Grove Resort Avenue #3703, Winter Garden 34787 $178,000 · 2 bd · 2 ba · 1,265 sqft
• 14075 Lochend Way, Winter Garden 34787 $499,900 · 4 bd · 3 ba · 2,197 sqft
• 11234 Silver Trumpet Loop, Winter Garden 34787 $415,000 · 2 bd · 2 ba · 1,515 sqft
• 14501 Grove Resort Avenue #2604, Winter Garden 34787 $165,000 · 2 bd · 2 ba · 1,375 sqft
• 6379 Argent Wood Drive, Winter Garden 34787 $459,690 · 3 bd · 3 ba · 1,652 sqft
• 11120 Suspense Drive, Winter Garden 34787 $389,900 · 3 bd · 3 ba · 1,636 sqft
• 14942 Windflower Alley, Winter Garden 34787 $391,000 · 3 bd · 3 ba · 1,536 sqft
• 15877 Tollington Alley, Winter Garden 34787 $483,500 · 3 bd · 3 ba · 1,835 sqft
• 17802 Jefferson Street, Winter Garden 34787 $425,000 · 4 bd · 2 ba · 1,778 sqft
• 14501 Grove Resort Avenue #3438, Winter Garden 34787 $174,900 · 3 bd · 2 ba · 1,396 sqft
• 15193 Aqua Sol Lane, Winter Garden 34787 $459,900 · 3 bd · 2 ba · 1,579 sqft
• 16570 Barbours Creek Way, Winter Garden 34787 $452,000 · 3 bd · 3 ba · 1,567 sqft