Homes under $500K in Winter Park, FL
97 for sale · 367 homes listed · Updated September 27, 2026 · Page 2 of 8
- 7302 swallow run #7302, Winter Park 32792 $134,900 · 2 bd · 2 ba · 756 sqft
- 3071 george mason avenue #5, Winter Park 32792 $89,900 · 1 ba · 549 sqft
- 2275 island run, Winter Park 32792 $299,990 · 3 bd · 2 ba · 1,467 sqft
- 2500 lee road #143, Winter Park 32789 $130,000 · 1 bd · 1 ba · 645 sqft
- 2112 eastbrook boulevard, Winter Park 32792 $423,000 · 3 bd · 2 ba · 1,470 sqft
- 2302 barbados drive, Winter Park 32792 $295,000 · 2 bd · 2 ba · 1,544 sqft
- 2017 canny cove, Winter Park 32792 $389,900 · 3 bd · 3 ba · 1,907 sqft
- 5588 garden grove circle, Winter Park 32792 $395,000 · 3 bd · 2 ba · 1,310 sqft
- 602 trinidad court #602, Winter Park 32792 $227,000 · 2 bd · 2 ba · 1,120 sqft
- 3209 heartwood avenue, Winter Park 32792 $449,900 · 4 bd · 2 ba · 1,627 sqft
- 2007 cornell avenue, Winter Park 32789 $449,000 · 3 bd · 2 ba · 1,154 sqft
- 7450 wynnewood square #189, Winter Park 32792 $170,000 · 2 bd · 3 ba · 1,031 sqft
- 1500 gay road #4d, Winter Park 32789 $164,500 · 1 bd · 1 ba · 732 sqft
- 1849 viburnum lane, Winter Park 32792 $389,900 · 4 bd · 2 ba · 1,627 sqft
- 3370 cedar springs place #156, Winter Park 32792 $179,990 · 2 bd · 3 ba · 1,031 sqft
- 192 balfour drive #2, Winter Park 32792 $319,000 · 2 bd · 2 ba · 1,287 sqft
- 2122 ridge drive, Winter Park 32792 $360,000 · 4 bd · 3 ba · 1,664 sqft
- 2008 houndslake drive, Winter Park 32792 $475,000 · 4 bd · 2 ba · 2,250 sqft
- 259 orange terrace drive, Winter Park 32789 $449,900 · 3 bd · 2 ba · 1,248 sqft
- 2305 sun valley circle, Winter Park 32792 $279,900 · 2 bd · 2 ba · 1,295 sqft
- 4870 seminole avenue, Winter Park 32792 $380,000 · 3 bd · 2 ba · 1,277 sqft
- 950 hanover avenue, Winter Park 32789 $439,000 · 3 bd · 2 ba · 1,606 sqft
- 2475 tahoe circle, Winter Park 32792 $268,000 · 2 bd · 2 ba · 1,295 sqft
- 2818 ambergate road, Winter Park 32792 $429,900 · 3 bd · 2 ba · 1,398 sqft
- 1660 orange avenue, Winter Park 32789 $479,900 · 3 bd · 2 ba · 1,614 sqft
- 1211 schultz avenue, Winter Park 32789 $475,000 · 3 bd · 2 ba · 1,085 sqft
- 1250 south denning drive #119, Winter Park 32789 $265,000 · 2 bd · 2 ba · 908 sqft
- 1000 south semoran boulevard #408, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 sqft
- 1000 south semoran boulevard #306, Winter Park 32792 $138,000 · 1 bd · 1 ba · 796 sqft
- 1000 south semoran boulevard #404, Winter Park 32792 $138,000 · 1 bd · 1 ba · 776 sqft
- 7522 aloma pines court, Winter Park 32792 $375,000 · 3 bd · 3 ba · 1,872 sqft
- 7393 grand avenue, Winter Park 32792 $325,000 · 3 bd · 2 ba · 1,518 sqft
- 7506 cranes creek court #30, Winter Park 32792 $365,000 · 3 bd · 3 ba · 1,861 sqft
- 5331 oak court, Winter Park 32792 $460,000 · 3 bd · 2 ba · 1,263 sqft
- 2923 antique oaks circle #34, Winter Park 32792 $180,000 · 2 bd · 2 ba · 1,105 sqft
- 885 carnation drive, Winter Park 32792 $368,000 · 4 bd · 2 ba · 1,240 sqft
- 5503 albert drive, Winter Park 32792 $399,900 · 3 bd · 2 ba · 1,366 sqft
- 310 granada drive, Winter Park 32789 $339,900 · 3 bd · 2 ba · 1,344 sqft
- 2568 lotafun avenue, Winter Park 32789 $395,000 · 3 bd · 2 ba · 1,201 sqft
- 205 lewfield circle #205, Winter Park 32792 $182,900 · 2 bd · 2 ba · 927 sqft
- 525 ololu drive, Winter Park 32789 $490,900 · 3 bd · 3 ba · 1,786 sqft
- 700 melrose avenue #j24, Winter Park 32789 $350,000 · 1 bd · 1 ba · 987 sqft
- 501 heritage boulevard, Winter Park 32792 $419,000 · 4 bd · 2 ba · 1,376 sqft
- 2500 lee road #104, Winter Park 32789 $242,400 · 2 bd · 2 ba · 956 sqft
- 173 scottsdale square #173, Winter Park 32792 $100,000 · 1 bd · 1 ba · 785 sqft
- 1695 lee road #c206, Winter Park 32789 $140,000 · 2 bd · 1 ba · 881 sqft
- 7786 fox knoll place, Winter Park 32792 $410,500 · 4 bd · 2 ba · 1,301 sqft
- 2651 cayman way, Winter Park 32792 Pending $255,000 · 2 bd · 2 ba · 1,020 sqft
- 630 killarney bay court 3, Winter Park 32789 Pending $475,000 · 2 bd · 3 ba · 1,428 sqft
- 2052 leanne court, Winter Park 32792 Pending $440,000 · 4 bd · 2 ba · 2,264 sqft