Homes under $500K in Winter Garden, FL

169 for sale · 577 homes listed · Updated September 27, 2026 · Page 5 of 12

• 16588 barbours creek way, Winter Garden 34787 Pending $414,990 · 3 bd · 3 ba · 1,567 sqft
• 15165 groveside road, Winter Garden 34787 Pending $489,890 · 4 bd · 4 ba · 1,846 sqft
• 455 westpoint garden circle, Winter Garden 34787 Pending $330,000 · 3 bd · 3 ba · 1,588 sqft
• 6258 sunny time avenue, Winter Garden 34787 Pending $434,490 · 3 bd · 3 ba · 1,553 sqft
• 11259 silver trumpet loop, Winter Garden 34787 Pending $432,619 · 2 bd · 2 ba · 1,515 sqft
• 6373 argent wood drive, Winter Garden 34787 Pending $488,190 · 4 bd · 3 ba · 1,847 sqft
• 2766 bobcat chase boulevard, Winter Garden 34787 Pending $499,900 · 3 bd · 3 ba · 1,811 sqft
• 17531 north sunset terrace, Winter Garden 34787 Pending $425,000 · 3 bd · 3 ba · 1,935 sqft
• 234 grand royal circle, Winter Garden 34787 Pending $389,990 · 3 bd · 2 ba · 1,534 sqft
• 17398 sweet moro drive, Winter Garden 34787 Pending $470,782 · 3 bd · 3 ba · 1,635 sqft
• 721 sunburst cove lane, Winter Garden 34787 Pending $440,000 · 4 bd · 2 ba · 1,878 sqft
• 16527 barbours creek way, Winter Garden 34787 Pending $414,990 · 3 bd · 3 ba · 1,567 sqft
• 16515 barbours creek way, Winter Garden 34787 Pending $414,990 · 3 bd · 3 ba · 1,567 sqft
• 16521 barbours creek way, Winter Garden 34787 Pending $414,990 · 3 bd · 3 ba · 1,567 sqft
• 2250 oakington street, Winter Garden 34787 Pending $438,000 · 3 bd · 2 ba · 1,636 sqft
• 16546 barbours creek way, Winter Garden 34787 Pending $414,990 · 3 bd · 3 ba · 1,567 sqft
• 16510 barbours creek way, Winter Garden 34787 Pending $447,500 · 3 bd · 3 ba · 1,567 sqft
• 16516 barbours creek way, Winter Garden 34787 Pending $424,990 · 3 bd · 3 ba · 1,567 sqft
• 17392 sweet moro drive, Winter Garden 34787 Pending $459,922 · 3 bd · 3 ba · 1,577 sqft
• 15873 gem view street, Winter Garden 34787 Pending $414,000 · 2 bd · 2 ba · 1,574 sqft
• 122 windtree lane o, Winter Garden 34787 Pending $229,900 · 2 bd · 2 ba · 918 sqft
• 9338 tyrella pine trail, Winter Garden 34787 Active Under Contract $425,000 · 4 bd · 3 ba · 1,696 sqft
• 1286 winter green way, Winter Garden 34787 Active Under Contract $219,900 · 2 bd · 2 ba · 1,144 sqft
• 2609 slagrove court, Winter Garden 34787 Active Under Contract $474,000 · 4 bd · 2 ba · 2,383 sqft
• 317 southern pecan circle 102, Winter Garden 34787 Active Under Contract $225,000 · 1 bd · 1 ba · 738 sqft
• 7007 twilight bay drive, Winter Garden 34787 Active Under Contract $465,000 · 3 bd · 3 ba · 1,845 sqft
• 14501 grove resort avenue 3621, Winter Garden 34787 Active Under Contract $174,950 · 2 bd · 2 ba · 1,375 sqft
• 16209 admirals cove lane, Winter Garden 34787 Active Under Contract $409,990 · 3 bd · 3 ba · 1,568 sqft
• 6212 aralia ivy lane, Winter Garden 34787 Active Under Contract $400,000 · 3 bd · 3 ba · 1,560 sqft
• 8012 bluejack oak drive, Winter Garden 34787 Active Under Contract $479,000 · 4 bd · 4 ba · 2,222 sqft
• 7036 bolanzo alley, Winter Garden 34787 Active Under Contract $470,000 · 4 bd · 4 ba · 1,920 sqft
• 12362 bracco street, Winter Garden 34787 Active Under Contract $485,000 · 4 bd · 3 ba · 2,094 sqft
• 12308 bracco street, Winter Garden 34787 Active Under Contract $485,000 · 4 bd · 3 ba · 2,094 sqft
• 1681 east spring ridge circle, Winter Garden 34787 Active Under Contract $424,900 · 4 bd · 2 ba · 1,858 sqft
• 342 windford court, Winter Garden 34787 Active Under Contract $319,900 · 3 bd · 2 ba · 1,194 sqft
• 1431 viscaya cove boulevard, Winter Garden 34787 Active Under Contract $499,900 · 4 bd · 3 ba · 2,030 sqft
• 14501 grove resort avenue 2315, Winter Garden 34787 Active Under Contract $180,000 · 2 bd · 2 ba · 1,265 sqft
• 12103 eastmoor drive, Winter Garden 34787 Active Under Contract $435,000 · 3 bd · 2 ba · 1,604 sqft
• 15025 evergreen oak loop, Winter Garden 34787 Active Under Contract $490,000 · 4 bd · 4 ba · 2,477 sqft
• 7279 duxbury lane, Winter Garden 34787 Active Under Contract $424,900 · 3 bd · 3 ba · 1,895 sqft
• 1503 coluso drive, Winter Garden 34787 Active Under Contract $443,000 · 3 bd · 2 ba · 2,187 sqft
• 14610 seton creek boulevard, Winter Garden 34787 Active Under Contract $488,000 · 3 bd · 3 ba · 1,916 sqft
• 231 doe run drive, Winter Garden 34787 Active Under Contract $494,995 · 4 bd · 2 ba · 1,972 sqft
• 17035 harbor oak parkway, Winter Garden 34787 Active Under Contract $485,000 · 3 bd · 2 ba · 1,692 sqft
• 1008 stucki terrace, Winter Garden 34787 Active Under Contract $215,000 · 2 bd · 2 ba · 814 sqft
• 1645 east spring ridge circle, Winter Garden 34787 Active Under Contract $439,000 · 3 bd · 2 ba · 1,219 sqft
• 142 southern pecan circle 205, Winter Garden 34787 Active Under Contract $297,900 · 3 bd · 2 ba · 1,453 sqft
• 1610 beulah road, Winter Garden 34787 Active Under Contract $450,000 · 4 bd · 2 ba · 2,210 sqft
• 14383 braemar street, Winter Garden 34787 Active Under Contract $456,000 · 3 bd · 3 ba · 1,678 sqft
• 1950 pantheon drive, Winter Garden 34787 Active Under Contract $489,000 · 3 bd · 2 ba · 1,754 sqft