Homes under $500K in Winter Garden, FL

169 for sale · 577 homes listed · Updated September 27, 2026 · Page 7 of 12

• 14501 grove resort avenue 3215, Winter Garden 34787 Off market since Jul 2026 $239,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 3712, Winter Garden 34787 Off market since Sep 2026 $325,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 3535, Winter Garden 34787 Off market since Sep 2026 $369,990 · 2 bd · 2 ba · 1,434 sqft
• 14501 grove resort avenue 3304, Winter Garden 34787 Off market since Sep 2026 $205,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 1407, Winter Garden 34787 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 1,544 sqft
• 634 foster avenue, Winter Garden 34787 Off market since Sep 2026 $285,000 · 2 bd · 1 ba · 696 sqft
• 14501 grove resort avenue 2536, Winter Garden 34787 Off market since Sep 2026 $314,900 · 2 bd · 2 ba · 1,434 sqft
• 12036 holystone street, Winter Garden 34787 Off market since Jul 2026 $455,000 · 3 bd · 3 ba · 1,817 sqft
• 14501 grove resort avenue 1105, Winter Garden 34787 Off market since Sep 2026 $304,000 · 2 bd · 2 ba · 1,265 sqft
• 22 windtree lane 203, Winter Garden 34787 Off market since Jul 2026 $169,900 · 2 bd · 2 ba · 918 sqft
• 14501 grove resort avenue 1622, Winter Garden 34787 Off market since Sep 2026 $449,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 2528, Winter Garden 34787 Off market since Sep 2026 $209,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 2527, Winter Garden 34787 Off market since Sep 2026 $215,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 2534, Winter Garden 34787 Off market since Sep 2026 $210,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1746, Winter Garden 34787 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 3228, Winter Garden 34787 Off market since Aug 2026 $240,000 · 3 bd · 3 ba · 1,544 sqft
• 92 windtree lane 201, Winter Garden 34787 Off market since Sep 2026 $218,000 · 2 bd · 2 ba · 918 sqft
• 373 eron way 47, Winter Garden 34787 Off market since Sep 2026 $182,000 · 2 bd · 2 ba · 840 sqft
• 14501 grove resort avenue 3424, Winter Garden 34787 Off market since Sep 2026 $230,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 1111, Winter Garden 34787 Off market since Sep 2026 $179,000 · 2 bd · 2 ba · 1,265 sqft
• 900 walkers grove lane, Winter Garden 34787 Off market since Aug 2026 $459,900 · 3 bd · 3 ba · 1,905 sqft
• 14501 grove resort avenue 1503, Winter Garden 34787 Off market since Sep 2026 $249,000 · 3 bd · 2 ba · 1,396 sqft
• 14051 grove resort avenue 1705, Winter Garden 34787 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 3128, Winter Garden 34787 Off market since Sep 2026 $250,000 · 3 bd · 3 ba · 1,544 sqft
• 9456 komika lane west 1, Winter Garden 34787 Off market since Jul 2026 $468,150 · 3 bd · 2 ba · 1,705 sqft
• 14501 grove resort avenue 1528, Winter Garden 34787 Off market since Aug 2026 $289,900 · 3 bd · 3 ba · 1,396 sqft
• 14501 grove resort avenue 1224, Winter Garden 34787 Off market since Sep 2026 $249,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 3135, Winter Garden 34787 Off market since Sep 2026 $250,000 · 2 bd · 2 ba · 1,434 sqft
• 14501 grove resort avenue 2604, Winter Garden 34787 Off market since Sep 2026 $165,000 · 2 bd · 2 ba · 1,375 sqft
• 14989 apollo bond drive, Winter Garden 34787 Off market since Sep 2026 $375,000 · 3 bd · 3 ba · 1,789 sqft
• 1532 scarlet oak loop 70b, Winter Garden 34787 Off market since Aug 2026 $336,900 · 3 bd · 3 ba · 1,544 sqft
• 17723 japonica bloom drive, Winter Garden 34787 Off market since Aug 2026 $414,900 · 3 bd · 3 ba · 1,584 sqft
• 14058 frasier street, Winter Garden 34787 Off market since Aug 2026 $459,000 · 4 bd · 3 ba · 1,996 sqft
• 14501 grove resort avenue 2223, Winter Garden 34787 Off market since Sep 2026 $244,990 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 1203, Winter Garden 34787 Off market since Sep 2026 $340,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1443, Winter Garden 34787 Off market since Sep 2026 $290,000 · 2 bd · 2 ba · 1,375 sqft
• 16425 prairie school drive, Winter Garden 34787 Off market since Sep 2026 $414,900 · 3 bd · 3 ba · 1,662 sqft
• 87 windtree lane k, Winter Garden 34787 Off market since Aug 2026 $199,999 · 2 bd · 2 ba · 918 sqft
• 14501 grove resort avenue 3611, Winter Garden 34787 Off market since Sep 2026 $199,900 · 3 bd · 2 ba · 1,396 sqft
• 8113 red stopper lane, Winter Garden 34787 Off market since Sep 2026 $434,900 · 3 bd · 3 ba · 1,725 sqft
• 14501 grove resort avenue 3109, Winter Garden 34787 Off market since Sep 2026 $299,900 · 2 bd · 2 ba · 1,434 sqft
• 225 southern pecan circle 208, Winter Garden 34787 Off market since Sep 2026 $279,900 · 2 bd · 2 ba · 1,264 sqft
• 16149 wind view lane, Winter Garden 34787 Off market since Aug 2026 $495,000 · 3 bd · 3 ba · 2,036 sqft
• 14501 grove resort avenue 1629, Winter Garden 34787 Off market since Sep 2026 $225,000 · 3 bd · 3 ba · 1,544 sqft
• 884 klondike street, Winter Garden 34787 Off market since Sep 2026 $372,500 · 4 bd · 2 ba · 1,485 sqft
• 14501 grove resort avenue 2530, Winter Garden 34787 Off market since Sep 2026 $215,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 2532, Winter Garden 34787 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,265 sqft
• 680 dunbar avenue, Winter Garden 34787 Off market since Jul 2026 $465,000 · 4 bd · 2 ba · 1,713 sqft
• 14501 grove resort avenue 1732, Winter Garden 34787 Off market since Sep 2026 $169,950 · 2 bd · 2 ba · 1,265 sqft
• 15659 jungle alley, Winter Garden 34787 Off market since Jul 2026 $435,000 · 3 bd · 3 ba · 1,732 sqft