Homes under $500K in Winter Garden, FL

236 homes for sale · Updated August 12, 2026 · Page 2 of 5

• 14501 grove resort avenue 1203, Winter Garden 34787 $340,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1443, Winter Garden 34787 $290,000 · 2 bd · 2 ba · 1,375 sqft
• 16425 prairie school drive, Winter Garden 34787 $419,900 · 3 bd · 3 ba · 1,662 sqft
• 14501 grove resort avenue 3611, Winter Garden 34787 $210,000 · 3 bd · 2 ba · 1,396 sqft
• 8113 red stopper lane, Winter Garden 34787 $434,900 · 3 bd · 3 ba · 1,725 sqft
• 14095 title way, Winter Garden 34787 $399,000 · 3 bd · 3 ba · 1,628 sqft
• 14501 grove resort avenue 3109, Winter Garden 34787 $299,900 · 2 bd · 2 ba · 1,434 sqft
• 225 southern pecan circle 208, Winter Garden 34787 $279,900 · 2 bd · 2 ba · 1,264 sqft
• 7007 twilight bay drive, Winter Garden 34787 $465,000 · 3 bd · 3 ba · 1,845 sqft
• 14501 grove resort avenue 1629, Winter Garden 34787 $290,000 · 3 bd · 3 ba · 1,544 sqft
• 884 klondike street, Winter Garden 34787 $372,500 · 4 bd · 2 ba · 1,485 sqft
• 14501 grove resort avenue 2530, Winter Garden 34787 $275,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 2532, Winter Garden 34787 $275,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 3621, Winter Garden 34787 $194,950 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 1732, Winter Garden 34787 $179,950 · 2 bd · 2 ba · 1,265 sqft
• 15353 oak apple court, Winter Garden 34787 $347,500 · 3 bd · 3 ba · 1,699 sqft
• 131 southern pecan circle 201, Winter Garden 34787 $235,000 · 1 bd · 1 ba · 738 sqft
• 6212 aralia ivy lane, Winter Garden 34787 $429,900 · 3 bd · 3 ba · 1,560 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 $333,000 · 3 bd · 3 ba · 1,544 sqft
• 16396 prairie school drive, Winter Garden 34787 $469,990 · 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 $339,000 · 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 $425,000 · 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, Winter Garden 34787 $329,900 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 3524, Winter Garden 34787 $299,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 2615, Winter Garden 34787 $249,000 · 2 bd · 2 ba · 1,265 sqft
• 8012 bluejack oak drive, Winter Garden 34787 $499,000 · 4 bd · 4 ba · 2,222 sqft
• 14280 braemar street, Winter Garden 34787 $499,000 · 3 bd · 3 ba · 1,964 sqft
• 2281 oakington street, Winter Garden 34787 $465,000 · 3 bd · 2 ba · 1,628 sqft
• 15357 oak apple court 4c, Winter Garden 34787 $329,500 · 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
• 12362 bracco street, Winter Garden 34787 $495,000 · 4 bd · 3 ba · 2,094 sqft
• 12003 holystone street, Winter Garden 34787 $445,000 · 3 bd · 3 ba · 1,814 sqft
• 15140 windflower alley, Winter Garden 34787 $405,000 · 3 bd · 3 ba · 1,536 sqft
• 14501 grove resort avenue 2214, Winter Garden 34787 $235,000 · 2 bd · 2 ba · 1,375 sqft