Homes under $500K in Winter Park, FL
97 for sale · 367 homes listed · Updated September 27, 2026 · Page 6 of 8
- 700 melrose avenue j24, Winter Park 32789 Off market since Sep 2026 $350,000 · 1 bd · 1 ba · 987 sqft
- 7522 aloma pines court, Winter Park 32792 Off market since Sep 2026 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 193 lewfield circle, Winter Park 32792 Off market since Sep 2026 $248,900 · 2 bd · 3 ba · 1,300 sqft
- 316 beckett court, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 2 ba · 1,651 sqft
- 200 saint andrews boulevard 704, Winter Park 32792 Off market since Sep 2026 $164,999 · 1 bd · 1 ba · 793 sqft
- 1320 gladiolas drive, Winter Park 32792 Off market since Sep 2026 $469,900 · 4 bd · 2 ba · 1,624 sqft
- 1840 aster drive, Winter Park 32792 Off market since Sep 2026 $389,950 · 3 bd · 2 ba · 1,667 sqft
- 5503 albert drive, Winter Park 32792 Off market since Sep 2026 $399,900 · 3 bd · 2 ba · 1,366 sqft
- 5340 north lake burkett lane, Winter Park 32792 Off market since Sep 2026 $424,900 · 3 bd · 2 ba · 1,746 sqft
- 2715 prince john road, Winter Park 32792 Off market since Sep 2026 $494,900 · 3 bd · 2 ba · 1,565 sqft
- 2500 lee road 220, Winter Park 32789 Off market since Sep 2026 $199,900 · 2 bd · 1 ba · 851 sqft
- 151 north orlando avenue 142, Winter Park 32789 Off market since Sep 2026 $199,900 · 1 bd · 1 ba · 582 sqft
- 1535 lawndale circle, Winter Park 32792 Off market since Sep 2026 $420,000 · 3 bd · 2 ba · 1,676 sqft
- 8433 commander cove, Winter Park 32792 Off market since Sep 2026 $455,000 · 4 bd · 3 ba · 1,903 sqft
- 2008 houndslake drive, Winter Park 32792 Off market since Sep 2026 $475,000 · 4 bd · 2 ba · 2,250 sqft
- 1605 puritan avenue, Winter Park 32792 Off market since Sep 2026 $379,000 · 3 bd · 2 ba · 1,285 sqft
- 4756 tangerine avenue 4756, Winter Park 32792 Off market since Sep 2026 $185,000 · 2 bd · 2 ba · 1,058 sqft
- 1500 gay road 3c, Winter Park 32789 Off market since Sep 2026 $235,000 · 2 bd · 2 ba · 1,026 sqft
- 2339 inagua way, Winter Park 32792 Off market since Sep 2026 $296,500 · 3 bd · 2 ba · 1,324 sqft
- 7733 country place g2, Winter Park 32792 Off market since Aug 2026 $229,500 · 2 bd · 2 ba · 1,068 sqft
- 2712 tortoise cove, Winter Park 32792 Off market since Sep 2026 $235,000 · 2 bd · 1 ba · 924 sqft
- 1564 lawndale circle, Winter Park 32792 Off market since Sep 2026 $450,000 · 4 bd · 3 ba · 1,980 sqft
- 7488 whisperwood drive 28, Winter Park 32792 Off market since Sep 2026 $199,000 · 2 bd · 3 ba · 1,578 sqft
- 259 orange terrace drive, Winter Park 32789 Off market since Sep 2026 $449,900 · 3 bd · 2 ba · 1,248 sqft
- 981 aragon avenue, Winter Park 32789 Off market since Sep 2026 $494,999 · 2 bd · 1 ba · 857 sqft
- 2041 jewell avenue, Winter Park 32789 Off market since Sep 2026 $439,900 · 3 bd · 1 ba · 1,508 sqft
- 1000 south semoran boulevard 306, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 796 sqft
- 1000 south semoran boulevard 408, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 776 sqft
- 1000 south semoran boulevard 404, Winter Park 32792 Off market since Sep 2026 $138,000 · 1 bd · 1 ba · 776 sqft
- 2372 sun valley circle 2372, Winter Park 32792 Off market since Sep 2026 $285,000 · 2 bd · 2 ba · 1,495 sqft
- 252 scottsdale square 252, Winter Park 32792 Off market since Sep 2026 $85,000 · 2 bd · 2 ba · 1,085 sqft
- 2305 sun valley circle, Winter Park 32792 Off market since Sep 2026 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 5184 lazy oaks drive, Winter Park 32792 Off market since Sep 2026 $275,000 · 2 bd · 2 ba · 1,008 sqft
- 1250 south denning drive 109, Winter Park 32789 Off market since Sep 2026 $190,000 · 1 bd · 1 ba · 658 sqft
- 3360 royal street, Winter Park 32792 Off market since Jul 2026 $179,900 · 2 bd · 2 ba · 981 sqft
- 2450 grand teton circle 2450, Winter Park 32792 Off market since Sep 2026 $250,000 · 3 bd · 2 ba · 1,311 sqft
- 303 scottsdale square 303, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 885 carnation drive, Winter Park 32792 Off market since Sep 2026 $368,000 · 4 bd · 2 ba · 1,240 sqft
- 263 scottsdale square 263, Winter Park 32792 Off market since Sep 2026 $80,000 · 2 bd · 2 ba · 1,020 sqft
- 1401 aster court, Winter Park 32792 Off market since Sep 2026 $414,900 · 4 bd · 2 ba · 1,653 sqft
- 2487 harbour way, Winter Park 32792 Off market since Sep 2026 $270,000 · 3 bd · 3 ba · 1,803 sqft
- 1500 gay road 4d, Winter Park 32789 Off market since Sep 2026 $164,500 · 1 bd · 1 ba · 732 sqft
- 7450 wynnewood square 189, Winter Park 32792 Off market since Sep 2026 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 2526 passamonte drive 10f, Winter Park 32792 Off market since Sep 2026 $335,000 · 3 bd · 3 ba · 1,790 sqft
- 2568 lotafun avenue, Winter Park 32789 Off market since Sep 2026 $395,000 · 3 bd · 2 ba · 1,201 sqft
- 2033 canny cove, Winter Park 32792 Off market since Sep 2026 $389,000 · 3 bd · 3 ba · 1,907 sqft
- 2703 tierra circle, Winter Park 32792 Off market since Sep 2026 $464,000 · 3 bd · 2 ba · 1,737 sqft
- 3562 bougainvillea drive, Winter Park 32792 Off market since Sep 2026 $334,000 · 3 bd · 2 ba · 1,149 sqft
- 5409 albert drive, Winter Park 32792 Off market since Sep 2026 $410,000 · 3 bd · 2 ba · 1,483 sqft
- 1000 south semoran boulevard 305, Winter Park 32792 Off market since Sep 2026 $115,000 · 1 bd · 1 ba · 735 sqft