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All Homes for Sale in Winter Park, FL — Page 2

Every home for sale in Winter Park, FL from the live MLS: 404 listings, newest first, 135 per page, 3 pages. Back to the Winter Park homes for sale hub for prices by ZIP, property type and community.

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  1. 1003 Golfside Drive · $759,900 · 3 bd/3 ba · 2,145 sq ft
  2. 2818 Ambergate Road · $429,900 · 3 bd/2 ba · 1,398 sq ft
  3. 1250 S Denning Drive #119 · $265,000 · 2 bd/2 ba · 908 sq ft
  4. 173 Scottsdale Square #173 · $100,000 · 1 bd/1 ba · 785 sq ft
  5. 698 N New York Avenue · $5,995,000 · 5 bd/5.5 ba · 5,096 sq ft
  6. 555 E Lake Sue Avenue · $2,095,000 · 4 bd/4 ba · 3,776 sq ft
  7. 1951 Winter Park Road · $1,949,000 · 4 bd/3.5 ba · 3,479 sq ft
  8. 2824 Prince John Road · $475,000 · 2 bd/2 ba · 1,438 sq ft
  9. 1660 Orange Avenue · $449,900 · 3 bd/2 ba · 1,614 sq ft
  10. 532 Langholm Drive · $2,990,000 · 5 bd/4.5 ba · 4,050 sq ft
  11. 2614 Parkland Drive · $1,890,000 · 4 bd/3.5 ba · 3,307 sq ft
  12. 100 S Virginia Avenue #201 · $1,450,000 · 3 bd/3 ba · 2,756 sq ft
  13. 3334 Young Street · $469,900 · 3 bd/2 ba · 1,706 sq ft
  14. 3209 Heartwood Avenue · $439,900 · 4 bd/2 ba · 1,627 sq ft
  15. 192 Balfour Drive #2 · $319,000 · 2 bd/2 ba · 1,287 sq ft
  16. 5080 Seminole Avenue · $299,900 · 3 bd/2 ba · 1,078 sq ft
  17. 160 W Rockwood Way · $3,395,000 · 5 bd/5.5 ba · 4,015 sq ft
  18. 533 Country Club Drive · $1,599,000 · 4 bd/3.5 ba · 2,942 sq ft
  19. 120 Broadview Avenue · $1,250,000 · 3 bd/2 ba · 1,747 sq ft
  20. 5303 Pine Lily Circle · $659,000 · 3 bd/2 ba · 2,265 sq ft
  21. 4260 Bear Gully Road · $585,000 · 4 bd/3.5 ba · 2,322 sq ft
  22. 2302 Barbados Drive · $275,000 · 2 bd/2 ba · 1,544 sq ft
  23. 7348 Grand Avenue · $255,000 · 3 bd/2 ba · 1,509 sq ft
  24. 1905 Bonanza Ct · $520,000 · 4 bd/2 ba · 1,774 sq ft
  25. 2136 Linden Road · $365,000 · 3 bd/1.5 ba · 1,185 sq ft · Pending
  26. 7453 Daniel Webster Drive #A5 · $150,000 · 2 bd/2 ba · 1,063 sq ft
  27. 1742 Temple Drive · $3,545,995 · 4 bd/5 ba · 3,658 sq ft
  28. 4027 Northlight Dr 4 · $259,900 · 2 bd/2 ba · 1,234 sq ft
  29. 3651 N Goldenrod Road #C109 · $165,000 · 2 bd/2 ba · 840 sq ft
  30. 901 Golfview Terrace · $6,795,000 · 5 bd/5.5 ba · 5,479 sq ft
  31. 662 Granville Drive · $3,495,000 · 5 bd/5.5 ba · 4,478 sq ft
  32. 1517 Harmon Avenue · $1,049,000 · 4 bd/3.5 ba · 2,135 sq ft
  33. 250 Carolina Avenue #202 · $649,000 · 3 bd/2 ba · 1,450 sq ft
  34. 2463 Grand Teton Circle #2463 · $249,000 · 3 bd/2.5 ba · 1,720 sq ft
  35. 1166 Palmer Avenue · $5,500,000 · 5 bd/6 ba · 5,181 sq ft
  36. 2572 Fifeshire Drive · $875,000 · 4 bd/2.5 ba · 2,578 sq ft
  37. 2215 Woodcrest Drive · $637,500 · 4 bd/2 ba · 1,688 sq ft
  38. 5233 Lake Howell Road · $562,000 · 4 bd/3 ba · 1,778 sq ft · Pending
  39. 825 Palmer Avenue · $5,195,900 · 5 bd/6 ba · 5,122 sq ft
  40. 1803 Barker Drive · $2,190,000 · 4 bd/3 ba · 3,463 sq ft
  41. 1271 Palmer Avenue · $2,125,000 · 4 bd/4.5 ba · 2,850 sq ft
  42. 443 Broadview Avenue · $999,000 · 4 bd/3 ba · 2,803 sq ft
  43. 913 Moss Lane · $950,000 · 3 bd/2 ba · 1,887 sq ft
  44. 311 E Morse Boulevard #4-5 · $895,000 · 2 bd/2 ba · 1,763 sq ft
  45. 2349 Shadowland Loop · $425,000 · 3 bd/2.5 ba · 1,755 sq ft
  46. 2301 Conifer Avenue · $405,000 · 4 bd/2 ba · 2,189 sq ft
  47. 702 Via Bella · $4,090,000 · 4 bd/5.5 ba · 3,720 sq ft
  48. 540 N Pennsylvania Avenue · $3,950,000 · 4 bd/2 ba · 1,652 sq ft
  49. 2626 Ambergate Road · $380,000 · 3 bd/1 ba · 1,143 sq ft · Pending
  50. 2383 Sun Valley Circle #2383 · $234,900 · 2 bd/2 ba · 1,295 sq ft
  51. 311 E Morse Boulevard #1-5 · $2,475,000 · 3 bd/3 ba · 2,316 sq ft
  52. 618 Blairshire Circle · $875,000 · 4 bd/3 ba · 1,876 sq ft
  53. 2410 Sherbrooke Road · $769,000 · 4 bd/2.5 ba · 2,141 sq ft
  54. 2211 King Richards Court · $529,000 · 4 bd/2 ba · 1,845 sq ft
  55. 7476 Woodburn Court #38 · $170,000 · 2 bd/2.5 ba · 1,031 sq ft
  56. 1257 Wading Waters Circle · $1,550,000 · 6 bd/5 ba · 5,239 sq ft
  57. 1773 Walnut Avenue · $2,725,000 · 5 bd/4.5 ba · 3,784 sq ft
  58. 2286 Marsh Sedge Lane · $770,000 · 4 bd/3 ba · 2,192 sq ft · Pending
  59. 2260 Coldstream Drive · $675,000 · 4 bd/2 ba · 1,509 sq ft
  60. 1016 Aragon Avenue · $650,000 · 4 bd/3 ba · 1,840 sq ft
  61. 1416 Border Drive · $620,000 · 3 bd/1 ba · 1,243 sq ft
  62. 2661 Via Tuscany · $5,500,000 · 4 bd/4.5 ba · 3,880 sq ft
  63. 1927 S Lakemont Avenue · $915,000 · 3 bd/3.5 ba · 2,093 sq ft
  64. 1287 Verdant Glade Place · $735,000 · 4 bd/3.5 ba · 3,020 sq ft
  65. 433 Gilbert Road · $669,900 · 3 bd/2 ba · 1,800 sq ft
  66. 3020 Nicholson Drive · $470,000 · 4 bd/2 ba · 1,756 sq ft
  67. 200 S Interlachen Avenue #350 · $2,350,000 · 3 bd/3.5 ba · 3,110 sq ft
  68. 508 Brechin Drive · $599,000 · 3 bd/2 ba · 1,783 sq ft
  69. 1250 S Denning Drive #127 · $245,000 · 2 bd/2 ba · 908 sq ft
  70. 7506 Cranes Creek Court #30 · $365,000 · 3 bd/2.5 ba · 1,861 sq ft
  71. 1525 Granville Drive · $4,595,000 · 5 bd/5.5 ba · 5,211 sq ft
  72. 943 Fairway Drive · $650,000 · 4 bd/3 ba · 2,067 sq ft
  73. 2275 Island Run · $279,999 · 3 bd/2 ba · 1,467 sq ft
  74. 1922 Hammerlin Avenue · $1,095,000 · 3 bd/2.5 ba · 1,873 sq ft
  75. 1320 Orchid Avenue · $1,350,000 · 4 bd/4 ba · 2,998 sq ft
  76. 720 Pansy Avenue · $1,295,000 · 3 bd/4 ba · 2,191 sq ft
  77. 4039 Cool Water Court · $739,777 · 4 bd/2 ba · 2,267 sq ft
  78. 1850 Bryan Avenue · $699,000 · 3 bd/2 ba · 1,563 sq ft
  79. 1278 S Pennsylvania Avenue #13 · $799,000 · 3 bd/2.5 ba · 1,957 sq ft
  80. 7530 Cranes Creek Court · $306,900 · 3 bd/2.5 ba · 1,545 sq ft
  81. 5108 Lazy Oaks Drive #5108 · $255,000 · 2 bd/2 ba · 1,008 sq ft
  82. 471 Holt Avenue · $925,000 · 4 bd/3 ba · 2,528 sq ft
  83. 1259 Indiana Avenue · $575,000 · 2 bd/2.5 ba · 1,648 sq ft
  84. 1220 Howell Branch Road · $950,000 · 3 bd/2 ba · 1,487 sq ft
  85. 1621 Chestnut Avenue · $845,000 · 3 bd/2.5 ba · 2,022 sq ft
  86. 151 N Orlando Avenue #242 · $269,000 · 2 bd/1 ba · 710 sq ft
  87. 2430 Chantilly Avenue · $1,550,000 · 4 bd/4 ba · 2,916 sq ft
  88. 1256 Melissa Court · $660,000 · 3 bd/3 ba · 1,690 sq ft
  89. 2207 Kindel Avenue · $1,575,000 · 3 bd/2.5 ba · 2,733 sq ft
  90. 751 Pansy Avenue · $1,875,000 · 3 bd/3.5 ba · 2,703 sq ft
  91. 276 Detmar Drive · $3,600,000 · 4 bd/5 ba · 4,202 sq ft
  92. 724 Monmouth Way · $759,675 · 5 bd/3.5 ba · 2,832 sq ft
  93. 1250 S Denning Dr #Unit 233 · $242,500 · 2 bd/2 ba · 913 sq ft
  94. 222 Lewfield Circle · $189,900 · 2 bd/2 ba · 953 sq ft
  95. 2181 Linden Road · $419,990 · 5 bd/3 ba · 1,442 sq ft
  96. 283 Sandlewood Trail #3 · $279,000 · 2 bd/2.5 ba · 960 sq ft
  97. 285 Lewfield Circle #285 · $147,000 · 1 bd/1 ba · 678 sq ft
  98. 1761 Legion Drive · $3,265,000 · 5 bd/5.5 ba · 4,949 sq ft
  99. 150 E Reading Way · $1,399,000 · 3 bd/2.5 ba · 2,080 sq ft
  100. 900 Carver Street · $659,000 · 3 bd/3 ba · 1,794 sq ft
  101. 7605 Aloma Pines Court · $349,000 · 3 bd/2.5 ba · 1,872 sq ft
  102. 7525 Lodge Pole Trail · $550,000 · 4 bd/2 ba · 1,936 sq ft
  103. 1660 Gladiolas Drive · $469,900 · 3 bd/2 ba · 2,047 sq ft
  104. 2667 Cochise Trail · $985,000 · 4 bd/3 ba · 2,868 sq ft · Pending
  105. 2857 Clever Lane · $394,500 · 3 bd/2.5 ba · 1,782 sq ft
  106. 120 Longbranch Road · $860,000 · 5 bd/3.5 ba · 3,284 sq ft
  107. 250 Carolina Avenue #205 · $739,000 · 2 bd/2 ba · 1,311 sq ft
  108. 1842 Puritan Avenue · $419,000 · 4 bd/2 ba · 1,836 sq ft
  109. 7384 Grand Avenue · $385,000 · 3 bd/2 ba · 1,162 sq ft
  110. 2017 Canny Cove · $379,998 · 3 bd/2.5 ba · 1,907 sq ft
  111. 2641 Carvell Court · $525,000 · 4 bd/2 ba · 2,126 sq ft
  112. 648 Worthington Drive · $2,700,000 · 5 bd/4.5 ba · 3,588 sq ft
  113. 620 Virginia Drive · $3,890,000 · 6 bd/5 ba · 4,677 sq ft
  114. 2622 Lake Howell Lane · $3,750,000 · 4 bd/3 ba · 3,377 sq ft
  115. 2343 Versailles Avenue · $1,699,000 · 4 bd/3.5 ba · 3,307 sq ft
  116. 1431 Palm Avenue · $799,999 · 2 bd/2 ba · 1,540 sq ft
  117. 2627 Ambergate Road · $530,000 · 4 bd/3 ba · 1,745 sq ft
  118. 1652 Berkshire Avenue · $429,000 · 3 bd/2 ba · 1,498 sq ft
  119. 1955 Eland Avenue · $405,000 · 3 bd/2 ba · 1,494 sq ft
  120. 1754 Taylor Avenue · $2,569,999 · 5 bd/4.5 ba · 3,670 sq ft
  121. 1546 Miller Avenue · $1,429,900 · 4 bd/3.5 ba · 2,984 sq ft
  122. 2477 Tahoe Circle #2477 · $247,000 · 2 bd/2 ba · 1,316 sq ft
  123. 2308 Mulbry Drive · $1,699,000 · 4 bd/3.5 ba · 2,530 sq ft
  124. 2407 Lafayette Avenue · $1,625,000 · 5 bd/4.5 ba · 3,133 sq ft
  125. 857 Brock Street · $4,350,000 · 5 bd/5.5 ba · 4,827 sq ft
  126. 1071 Aragon Avenue · $575,000 · 2 bd/2.5 ba · 1,851 sq ft
  127. 1840 Bryan Avenue · $1,725,000 · 4 bd/3.5 ba · 3,727 sq ft
  128. 1500 Gay Road #4D · $159,900 · 1 bd/1 ba · 732 sq ft
  129. 722 S Ranger Boulevard · $775,000 · 4 bd/3 ba · 2,164 sq ft
  130. 1122 Wildmeadow Run · $660,000 · 4 bd/2.5 ba · 1,770 sq ft
  131. 1695 Lee Road #D107 · $180,000 · 1 bd/1 ba · 638 sq ft
  132. 4026 Tenita Drive · $599,000 · 3 bd/2 ba · 2,031 sq ft
  133. 5316 Halyard Court · $495,000 · 3 bd/2 ba · 1,380 sq ft
  134. 7413 Belle River Court #3 · $214,900 · 3 bd/2.5 ba · 1,151 sq ft
  135. 333 Cornwall Road · $549,900 · 4 bd/2 ba · 1,660 sq ft · Pending

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Updated November 8, 2026. Listing data from the MLS, deemed reliable but not guaranteed.

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