Homes under $500K in Winter Garden, FL

169 for sale · 577 homes listed · Updated September 27, 2026 · Page 9 of 12

• 14501 grove resort avenue 3211, Winter Garden 34787 Off market since Sep 2026 $271,000 · 3 bd · 2 ba · 1,396 sqft
• 15625 boggy oak circle 108b, Winter Garden 34787 Off market since Sep 2026 $335,000 · 3 bd · 3 ba · 1,419 sqft
• 15568 blackbead street, Winter Garden 34787 Sold on Jul 17, 2026 $435,000 · 4 bd · 3 ba · 1,861 sqft
• 14501 grove resort avenue 3429, Winter Garden 34787 Off market since Sep 2026 $298,900 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2616, Winter Garden 34787 Off market since Sep 2026 $200,000 · 3 bd · 2 ba · 1,396 sqft
• 516 south highland avenue, Winter Garden 34787 Off market since Sep 2026 $495,000 · 3 bd · 2 ba · 1,716 sqft
• 14200 avalon road 409, Winter Garden 34787 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,253 sqft
• 7030 twilight bay drive, Winter Garden 34787 Off market since Sep 2026 $469,000 · 4 bd · 4 ba · 1,920 sqft
• 12253 south bracco street, Winter Garden 34787 Off market since Sep 2026 $499,000 · 3 bd · 3 ba · 1,788 sqft
• 420 east cypress street, Winter Garden 34787 Off market since Sep 2026 $410,000 · 3 bd · 2 ba · 1,616 sqft
• 11025 suspense drive, Winter Garden 34787 Off market since Sep 2026 $410,000 · 3 bd · 3 ba · 1,636 sqft
• 1906 sherbourne street, Winter Garden 34787 Sold on Sep 3, 2026 $477,000 · 4 bd · 3 ba · 2,029 sqft
• 15806 gem view street, Winter Garden 34787 Off market since Sep 2026 $465,000 · 2 bd · 2 ba · 1,574 sqft
• 338 windford court, Winter Garden 34787 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,050 sqft
• 200 southern pecan circle 206, Winter Garden 34787 Off market since Sep 2026 $249,950 · 2 bd · 2 ba · 1,276 sqft
• 13861 easdale alley, Winter Garden 34787 Off market since Sep 2026 $499,000 · 4 bd · 3 ba · 2,031 sqft
• 15511 campden street, Winter Garden 34787 Off market since Sep 2026 $359,999 · 3 bd · 3 ba · 1,916 sqft
• 5686 cypress hill road, Winter Garden 34787 Off market since Aug 2026 $399,000 · 3 bd · 3 ba · 1,712 sqft
• 6131 elfin herb way, Winter Garden 34787 Off market since Sep 2026 $435,000 · 3 bd · 3 ba · 1,714 sqft
• 1701 east bay street, Winter Garden 34787 Off market since Sep 2026 $289,000 · 2 bd · 2 ba · 825 sqft
• 14501 grove resort avenue 3425, Winter Garden 34787 Off market since Sep 2026 $480,000 · 2 bd · 2 ba · 1,265 sqft
• 14903 driftwater drive, Winter Garden 34787 Off market since Sep 2026 $370,000 · 3 bd · 3 ba · 1,745 sqft
• 12830 sunset walk drive, Winter Garden 34787 Off market since Sep 2026 $471,000 · 3 bd · 3 ba · 1,857 sqft
• 1300 eastern pecan place 102, Winter Garden 34787 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,152 sqft
• 411 millwood place, Winter Garden 34787 Off market since Sep 2026 $459,000 · 3 bd · 2 ba · 1,696 sqft
• 5754 surprise lily drive, Winter Garden 34787 Off market since Sep 2026 $475,000 · 4 bd · 3 ba · 2,128 sqft
• 9362 woodcrane drive, Winter Garden 34787 Off market since Sep 2026 $435,800 · 3 bd · 3 ba · 2,058 sqft
• 13232 daniels landing circle, Winter Garden 34787 Off market since Sep 2026 $325,000 · 2 bd · 3 ba · 1,232 sqft
• 12042 grandrose alley, Winter Garden 34787 Off market since Aug 2026 $420,000 · 3 bd · 3 ba · 1,732 sqft
• 14501 grove resort avenue 1527, Winter Garden 34787 Off market since Sep 2026 $170,000 · 2 bd · 2 ba · 1,265 sqft
• 304 eron way 2, Winter Garden 34787 Off market since Sep 2026 $159,900 · 2 bd · 2 ba · 840 sqft
• 9078 wading walk lane, Winter Garden 34787 Off market since Jul 2026 $460,000 · 3 bd · 3 ba · 1,814 sqft
• 5863 cypress hill road, Winter Garden 34787 Off market since Sep 2026 $369,900 · 2 bd · 3 ba · 1,594 sqft
• 434 sand lime road, Winter Garden 34787 Off market since Sep 2026 $239,900 · 2 bd · 2 ba · 1,302 sqft
• 14501 grove resort avenue 3227, Winter Garden 34787 Off market since Jul 2026 $365,000 · 3 bd · 3 ba · 1,544 sqft
• 397 eron way 42, Winter Garden 34787 Off market since Sep 2026 $199,999 · 3 bd · 2 ba · 930 sqft
• 721 south woodland street, Winter Garden 34787 Off market since Sep 2026 $440,000 · 2 bd · 1 ba · 1,034 sqft
• 16435 hamlin hills road, Winter Garden 34787 Off market since Sep 2026 $449,999 · 3 bd · 3 ba · 1,736 sqft
• 1300 eastern pecan place 208, Winter Garden 34787 Off market since Sep 2026 $287,000 · 3 bd · 2 ba · 1,453 sqft
• 8019 jeremy joseph alley, Winter Garden 34787 Off market since Sep 2026 $389,900 · 3 bd · 3 ba · 1,696 sqft
• 14942 windflower alley, Winter Garden 34787 Off market since Sep 2026 $391,000 · 3 bd · 3 ba · 1,536 sqft
• 14031 picard alley, Winter Garden 34787 Off market since Sep 2026 $380,000 · 3 bd · 3 ba · 1,789 sqft
• 14501 grove resort avenue 3303, Winter Garden 34787 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,265 sqft
• 13158 bounty avenue, Winter Garden 34787 Off market since Sep 2026 $395,000 · 3 bd · 3 ba · 1,567 sqft
• 13349 harbor shore lane, Winter Garden 34787 Off market since Sep 2026 $307,000 · 2 bd · 3 ba · 1,236 sqft
• 417 southern pecan circle 202, Winter Garden 34787 Off market since Sep 2026 $212,000 · 1 bd · 1 ba · 942 sqft
• 359 douglas way 54, Winter Garden 34787 Off market since Sep 2026 $214,000 · 2 bd · 2 ba · 930 sqft
• 417 southern pecan circle 201, Winter Garden 34787 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,264 sqft
• 689 bethune avenue, Winter Garden 34787 Off market since Sep 2026 $399,000 · 4 bd · 2 ba · 1,434 sqft
• 14014 scarlet aster alley, Winter Garden 34787 Off market since Sep 2026 $449,000 · 3 bd · 3 ba · 1,808 sqft