Homes under $1M in Winter Park, FL
157 for sale · 591 homes listed · Updated September 27, 2026 · Page 4 of 12
- 1660 gladiolas drive, Winter Park 32792 $509,900 · 3 bd · 2 ba · 2,047 sqft
- 1061 aragon avenue #1061, Winter Park 32789 $510,000 · 3 bd · 3 ba · 1,669 sqft
- 2500 lee road #104, Winter Park 32789 $242,400 · 2 bd · 2 ba · 956 sqft
- 1003 golfside drive, Winter Park 32792 $769,900 · 3 bd · 3 ba · 2,145 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
- 1836 grinnell terrace, Winter Park 32789 Pending $999,000 · 3 bd · 2 ba · 1,907 sqft
- 1760 peruvian lane, Winter Park 32792 Pending $324,000 · 3 bd · 2 ba · 1,160 sqft
- 1807 hammerlin avenue g, Winter Park 32789 Pending $499,000 · 3 bd · 3 ba · 1,818 sqft
- 758 warrenton road, Winter Park 32792 Pending $318,985 · 3 bd · 2 ba · 1,196 sqft
- 1261 indiana avenue, Winter Park 32789 Pending $540,000 · 3 bd · 3 ba · 1,660 sqft
- 3282 oak lake place 3282, Winter Park 32792 Pending $154,500 · 2 bd · 2 ba · 990 sqft
- 2973 sanbina street, Winter Park 32789 Pending $377,880 · 3 bd · 2 ba · 1,128 sqft
- 1850 aster drive, Winter Park 32792 Pending $485,000 · 4 bd · 3 ba · 1,656 sqft
- 2500 lee road 104, Winter Park 32789 Pending $242,400 · 2 bd · 2 ba · 956 sqft
- 1521 cavendish road, Winter Park 32789 Pending $470,000 · 2 bd · 1 ba · 1,036 sqft
- 410 saint dunstan way, Winter Park 32792 Pending $500,000 · 3 bd · 2 ba · 1,512 sqft
- 751 warrenton road, Winter Park 32792 Pending $319,900 · 3 bd · 2 ba · 1,196 sqft
- 644 north knowles avenue 3, Winter Park 32789 Pending $424,400 · 1 bd · 1 ba · 767 sqft
- 1622 arbor park drive, Winter Park 32789 Pending $695,000 · 3 bd · 2 ba · 1,351 sqft
- 1956 japonica road, Winter Park 32792 Pending $549,000 · 3 bd · 2 ba · 1,923 sqft
- 7509 glenmoor lane, Winter Park 32792 Pending $499,500 · 3 bd · 2 ba · 2,067 sqft
- 7500 waunatta court, Winter Park 32792 Pending $299,900 · 3 bd · 2 ba · 1,998 sqft
- 3621 hawthorne lane, Winter Park 32792 Pending $415,000 · 3 bd · 2 ba · 1,525 sqft
- 1695 lee road b108, Winter Park 32789 Pending $88,999 · 1 bd · 1 ba · 638 sqft
- 5781 shale court, Winter Park 32792 Pending $300,000 · 2 bd · 2 ba · 1,086 sqft
- 2223 conifer avenue, Winter Park 32792 Pending $435,000 · 3 bd · 2 ba · 1,620 sqft
- 2504 forfarshire drive, Winter Park 32792 Pending $630,000 · 3 bd · 2 ba · 1,915 sqft
- 3373 cedar springs place 149, Winter Park 32792 Pending $171,900 · 2 bd · 3 ba · 1,031 sqft
- 3321 royal street, Winter Park 32792 Pending $280,000 · 3 bd · 2 ba · 1,197 sqft
- 2511 eastbrook boulevard, Winter Park 32792 Pending $365,000 · 3 bd · 2 ba · 1,520 sqft
- 7026 hammock way, Winter Park 32792 Pending $362,000 · 3 bd · 2 ba · 1,257 sqft
- 2560 franklin avenue, Winter Park 32789 Pending $479,000 · 4 bd · 2 ba · 1,514 sqft
- 5444 peaco place, Winter Park 32792 Pending $250,000 · 2 bd · 2 ba · 924 sqft
- 228 rippling lane, Winter Park 32789 Pending $540,000 · 3 bd · 2 ba · 1,618 sqft
- 7261 abbey lane, Winter Park 32792 Pending $350,000 · 3 bd · 2 ba · 1,268 sqft
- 2653 cayman way, Winter Park 32792 Pending $284,000 · 3 bd · 2 ba · 1,284 sqft
- 3328 hamlet loop, Winter Park 32792 Pending $349,900 · 3 bd · 2 ba · 1,397 sqft
- 1533 springtime loop, Winter Park 32792 Pending $415,000 · 3 bd · 2 ba · 1,192 sqft
- 1333 south denning drive, Winter Park 32789 Pending $299,000 · 2 bd · 1 ba · 702 sqft
- 1915 carrigan avenue, Winter Park 32792 Pending $299,900 · 3 bd · 1 ba · 1,520 sqft
- 950 south kentucky avenue, Winter Park 32789 Pending $799,000 · 4 bd · 3 ba · 2,155 sqft
- 1905 bonanza court, Winter Park 32792 Pending $520,000 · 4 bd · 2 ba · 1,774 sqft
- 1246 verdant glade place, Winter Park 32792 Pending $765,000 · 4 bd · 4 ba · 2,137 sqft
- 2168 ridge drive, Winter Park 32792 Pending $299,000 · 3 bd · 1 ba · 1,208 sqft
- 2313 knoll street, Winter Park 32792 Pending $299,000 · 3 bd · 2 ba · 1,235 sqft