Homes under $500K in Winter Garden, FL

169 for sale · 577 homes listed · Updated September 27, 2026 · Page 6 of 12

• 217 west story road, Winter Garden 34787 Active Under Contract $450,000 · 3 bd · 2 ba · 1,120 sqft
• 14629 bahama swallow boulevard, Winter Garden 34787 Active Under Contract $467,500 · 3 bd · 2 ba · 2,223 sqft
• 14230 murcott blossom boulevard, Winter Garden 34787 Active Under Contract $479,000 · 3 bd · 3 ba · 1,950 sqft
• 8150 red stopper lane, Winter Garden 34787 Active Under Contract $405,000 · 3 bd · 3 ba · 1,738 sqft
• 16161 mangrove road, Winter Garden 34787 Active Under Contract $499,900 · 3 bd · 3 ba · 2,200 sqft
• 14268 braemar street, Winter Garden 34787 Active Under Contract $485,000 · 4 bd · 3 ba · 2,070 sqft
• 1830 morning sky drive, Winter Garden 34787 Active Under Contract $465,000 · 3 bd · 3 ba · 2,145 sqft
• 15514 campden street, Winter Garden 34787 Active Under Contract $375,000 · 3 bd · 3 ba · 1,917 sqft
• 15190 sunrise grove court, Winter Garden 34787 Active Under Contract $400,000 · 3 bd · 3 ba · 1,902 sqft
• 13640 splashing isla drive, Winter Garden 34787 Active Under Contract $409,000 · 2 bd · 2 ba · 1,574 sqft
• 241 deepcove road, Winter Garden 34787 Active Under Contract $309,000 · 2 bd · 3 ba · 1,234 sqft
• 405 southern pecan circle 108, Winter Garden 34787 Active Under Contract $244,000 · 2 bd · 2 ba · 1,152 sqft
• 130 southern pecan circle 103, Winter Garden 34787 Active Under Contract $259,000 · 2 bd · 2 ba · 1,152 sqft
• 16954 tradewind point, Winter Garden 34787 Active Under Contract $482,000 · 3 bd · 2 ba · 1,692 sqft
• 1312 corsino street, Winter Garden 34787 Active Under Contract $435,000 · 3 bd · 2 ba · 1,307 sqft
• 10648 words drive, Winter Garden 34787 Active Under Contract $418,400 · 3 bd · 3 ba · 1,636 sqft
• 1097 depot court, Winter Garden 34787 Active Under Contract $479,900 · 3 bd · 2 ba · 1,583 sqft
• 242 winter nellis circle, Winter Garden 34787 Active Under Contract $359,999 · 3 bd · 3 ba · 1,991 sqft
• 445 spring leap circle, Winter Garden 34787 Active Under Contract $419,900 · 4 bd · 2 ba · 1,695 sqft
• 15819 gem view street, Winter Garden 34787 Active Under Contract $400,000 · 2 bd · 2 ba · 1,574 sqft
• 427 regal downs circle, Winter Garden 34787 Active Under Contract $475,000 · 5 bd · 3 ba · 2,135 sqft
• 1424 scarlet oak loop, Winter Garden 34787 Active Under Contract $379,000 · 3 bd · 3 ba · 1,737 sqft
• 1345 winter green way, Winter Garden 34787 Active Under Contract $225,000 · 2 bd · 2 ba · 1,259 sqft
• 5887 cypress hill road, Winter Garden 34787 Active Under Contract $450,000 · 3 bd · 3 ba · 1,810 sqft
• 8931 doddington way, Winter Garden 34787 Active Under Contract $479,000 · 3 bd · 3 ba · 1,944 sqft
• 15579 honeybell drive, Winter Garden 34787 Active Under Contract $399,000 · 3 bd · 3 ba · 1,727 sqft
• 14501 grove resort avenue 3439, Winter Garden 34787 Off market since Jul 2026 $320,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 3205, Winter Garden 34787 Off market since Sep 2026 $325,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 1220, Winter Garden 34787 Off market since Sep 2026 $325,890 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 3538, Winter Garden 34787 Off market since Sep 2026 $351,450 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 1637, Winter Garden 34787 Off market since Sep 2026 $235,100 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 1237, Winter Garden 34787 Off market since Sep 2026 $210,000 · 2 bd · 2 ba · 1,375 sqft
• 16353 lakelet alley, Winter Garden 34787 Sold on Jul 28, 2026 $444,990 · 3 bd · 3 ba · 1,567 sqft
• 14501 grove resort avenue 1707, Winter Garden 34787 Off market since Jul 2026 $325,000 · 3 bd · 3 ba · 1,544 sqft
• 14501 grove resort avenue 3406, Winter Garden 34787 Off market since Jul 2026 $204,000 · 2 bd · 2 ba · 1,265 sqft
• 14536 golden harbor lane, Winter Garden 34787 Off market since Aug 2026 $450,000 · 3 bd · 3 ba · 1,904 sqft
• 14501 grove resort avenue 2119, Winter Garden 34787 Off market since Jul 2026 $224,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2623, Winter Garden 34787 Off market since Sep 2026 $390,000 · 2 bd · 2 ba · 1,265 sqft
• 14501 grove resort avenue 3202, Winter Garden 34787 Off market since Sep 2026 $350,000 · 3 bd · 2 ba · 1,396 sqft
• 14501 grove resort avenue 2334, Winter Garden 34787 Off market since Sep 2026 $274,900 · 3 bd · 2 ba · 1,396 sqft
• 10534 tribute drive, Winter Garden 34787 Off market since Sep 2026 $419,000 · 3 bd · 3 ba · 1,636 sqft
• 10540 tribute drive, Winter Garden 34787 Off market since Sep 2026 $419,000 · 3 bd · 3 ba · 1,636 sqft
• 15695 grove resort avenue 4417, Winter Garden 34787 Off market since Sep 2026 $150,000 · 1 ba · 350 sqft
• 14501 grove resort avenue 1440, Winter Garden 34787 Off market since Sep 2026 $245,000 · 2 bd · 2 ba · 1,375 sqft
• 16105 water spring boulevard, Winter Garden 34787 Off market since Sep 2026 $497,000 · 4 bd · 3 ba · 2,042 sqft
• 330 southern pecan circle 208, Winter Garden 34787 Off market since Sep 2026 $298,000 · 3 bd · 2 ba · 1,453 sqft
• 14501 grove resort avenue 1612, Winter Garden 34787 Off market since Sep 2026 $299,000 · 2 bd · 2 ba · 1,375 sqft
• 14501 grove resort avenue 2101, Winter Garden 34787 Off market since Sep 2026 $460,000 · 3 bd · 3 ba · 1,544 sqft
• 16329 prairie school drive, Winter Garden 34787 Off market since Jul 2026 $490,000 · 4 bd · 3 ba · 2,070 sqft
• 14501 grove resort avenue 1545, Winter Garden 34787 Sold on Jul 20, 2026 $165,000 · 2 bd · 2 ba · 1,265 sqft