Homes under $500K in Winter Garden, FL

253 for sale · 414 homes listed · Updated September 25, 2026 · Page 2 of 9

• 131 southern pecan circle 201, Winter Garden 34787 $218,500 · 1 bd · 1 ba · 738 sqft
• 10089 salt point drive, Winter Garden 34787 $465,000 · 3 bd · 3 ba · 1,654 sqft
• 5413 new independence parkway, Winter Garden 34787 $488,000 · 4 bd · 3 ba · 2,131 sqft
• 14501 grove resort avenue 1703, Winter Garden 34787 $299,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1310, Winter Garden 34787 $215,000 · 2 bd · 2 ba · 1,265 sqft
• 15316 oak apple court b, Winter Garden 34787 $310,000 · 3 bd · 3 ba · 1,544 sqft
• 16396 prairie school drive, Winter Garden 34787 $464,990 · 3 bd · 3 ba · 2,070 sqft
• 14501 grove resort avenue 1721, Winter Garden 34787 $249,500 · 3 bd · 2 ba · 1,396 sqft
• 483 pennsylvania avenue, Winter Garden 34787 $334,000 · 2 bd · 2 ba · 1,008 sqft
• 14501 grove resort avenue 2423, Winter Garden 34787 $250,000 · 2 bd · 2 ba · 1,265 sqft
• 15187 harrowgate way, Winter Garden 34787 $415,000 · 3 bd · 2 ba · 1,296 sqft
• 15755 water spring boulevard, Winter Garden 34787 $420,000 · 3 bd · 3 ba · 1,636 sqft
• 12050 bracco street, Winter Garden 34787 $449,000 · 3 bd · 3 ba · 1,770 sqft
• 14501 grove resort avenue 1114, Winter Garden 34787 $239,500 · 3 bd · 3 ba · 1,544 sqft
• 5618 water rose road, Winter Garden 34787 $375,000 · 3 bd · 3 ba · 1,755 sqft
• 14501 grove resort avenue 2615, Winter Garden 34787 $249,000 · 2 bd · 2 ba · 1,265 sqft
• 14280 braemar street, Winter Garden 34787 $499,000 · 3 bd · 3 ba · 1,964 sqft
• 2281 oakington street, Winter Garden 34787 $439,000 · 3 bd · 2 ba · 1,628 sqft
• 15357 oak apple court 4c, Winter Garden 34787 $310,000 · 3 bd · 3 ba · 1,699 sqft
• 14501 grove resort avenue 3737, Winter Garden 34787 $350,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2413, Winter Garden 34787 $235,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 1614, Winter Garden 34787 $325,000 · 3 bd · 3 ba · 1,544 sqft
• 143 southern pecan circle 206, Winter Garden 34787 $279,900 · 2 bd · 2 ba · 1,276 sqft
• 14501 grove resort avenue 3630, Winter Garden 34787 $284,500 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 2635, Winter Garden 34787 $320,000 · 2 bd · 2 ba · 1,434 sqft
• 14099 lochend way, Winter Garden 34787 $468,000 · 3 bd · 3 ba · 1,720 sqft
• 12003 holystone street, Winter Garden 34787 $430,000 · 3 bd · 3 ba · 1,814 sqft
• 15140 windflower alley, Winter Garden 34787 $402,000 · 3 bd · 3 ba · 1,536 sqft
• 14501 grove resort avenue 2214, Winter Garden 34787 $235,000 · 2 bd · 2 ba · 1,375 sqft
• 9231 grand island way, Winter Garden 34787 $495,000 · 4 bd · 3 ba · 2,060 sqft
• 11072 silver surfer alley, Winter Garden 34787 $435,000 · 3 bd · 3 ba · 1,770 sqft
• 5545 bowman drive, Winter Garden 34787 $430,000 · 2 bd · 3 ba · 1,998 sqft
• 11117 bostwick alley, Winter Garden 34787 $485,000 · 3 bd · 2 ba · 1,685 sqft
• 10294 merrymeeting bay drive, Winter Garden 34787 $449,900 · 3 bd · 2 ba · 1,689 sqft
• 14501 grove resort avenue 1535, Winter Garden 34787 $410,990 · 3 bd · 2 ba · 1,396 sqft
• 170 windtree lane, Winter Garden 34787 $204,900 · 2 bd · 2 ba · 918 sqft
• 14501 grove resort avenue 1439, Winter Garden 34787 $169,900 · 2 bd · 2 ba · 1,265 sqft
• 12597 encore at ovation way, Winter Garden 34787 $459,000 · 3 bd · 3 ba · 2,322 sqft
• 14501 grove resort avenue 3211, Winter Garden 34787 $271,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort 1304, Winter Garden 34787 $350,000 · 3 bd · 2 ba · 1,396 sqft
• 15625 boggy oak circle 108b, Winter Garden 34787 $335,000 · 3 bd · 3 ba · 1,419 sqft
• 14501 grove resort avenue 3429, Winter Garden 34787 $298,900 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2616, Winter Garden 34787 $200,000 · 3 bd · 2 ba · 1,396 sqft
• 516 south highland avenue, Winter Garden 34787 $495,000 · 3 bd · 2 ba · 1,716 sqft
• 14200 avalon road 409, Winter Garden 34787 $215,000 · 2 bd · 2 ba · 1,253 sqft
• 14501 grove 3425, Winter Garden 34787 $420,000 · 2 bd · 2 ba
• 7030 twilight bay drive, Winter Garden 34787 $469,000 · 4 bd · 4 ba · 1,920 sqft
• 12253 south bracco street, Winter Garden 34787 $499,000 · 3 bd · 3 ba · 1,788 sqft
• 420 east cypress street, Winter Garden 34787 $410,000 · 3 bd · 2 ba · 1,616 sqft
• 11025 suspense drive, Winter Garden 34787 $410,000 · 3 bd · 3 ba · 1,636 sqft