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All Homes for Sale in Winter Park, FL — Page 3

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. 125 S Interlachen Avenue #1 · $3,645,000 · 3 bd/4 ba · 3,878 sq ft
  2. 1000 S Semoran Boulevard #302 · $97,000 · 1 bd/1 ba · 796 sq ft
  3. 125 S Interlachen Avenue #2 · $2,995,000 · 3 bd/4 ba · 3,244 sq ft
  4. 1061 Aragon Avenue #1061 · $510,000 · 3 bd/2.5 ba · 1,669 sq ft
  5. 3740 Hawthorne Lane · $430,000 · 3 bd/2 ba · 1,645 sq ft
  6. 2475 Tahoe Circle · $268,000 · 2 bd/2 ba · 1,295 sq ft
  7. 777 Halifax Avenue · $1,449,000 · 5 bd/4.5 ba · 3,109 sq ft
  8. 3562 Bougainvillea Drive · $334,000 · 3 bd/2 ba · 1,149 sq ft
  9. 1886 Clematis Lane · $425,000 · 3 bd/2 ba · 1,238 sq ft
  10. 5409 Albert Drive · $400,000 · 3 bd/2 ba · 1,483 sq ft
  11. 1000 S Semoran Boulevard #305 · $115,000 · 1 bd/1 ba · 735 sq ft
  12. 1420 Magnolia Avenue · $1,690,000 · 4 bd/3.5 ba · 3,174 sq ft
  13. 2412 Chantilly Avenue · $2,394,500 · 5 bd/6.5 ba · 4,506 sq ft
  14. 2033 Canny Cove · $389,000 · 3 bd/2.5 ba · 1,907 sq ft
  15. 281 Brewer Avenue · $1,800,000 · 5 bd/4.5 ba · 4,029 sq ft
  16. 2703 Tierra Circle · $449,000 · 3 bd/2 ba · 1,737 sq ft
  17. 885 Carnation Drive · $368,000 · 4 bd/2 ba · 1,240 sq ft
  18. 1003 Lake Bell Drive · $549,900 · 3 bd/2 ba · 1,837 sq ft
  19. 1261 Indiana Avenue · $540,000 · 3 bd/2.5 ba · 1,660 sq ft · Pending
  20. 240 Killarney Drive · $1,175,000 · 3 bd/2.5 ba · 1,329 sq ft
  21. 230 Killarney Drive · $1,150,000 · 4 bd/1 ba · 1,260 sq ft
  22. 1562 Arbor Park Drive · $775,000 · 4 bd/2.5 ba · 1,899 sq ft
  23. 2526 Passamonte Drive #10F · $335,000 · 3 bd/2.5 ba · 1,790 sq ft
  24. 1133 Bella Lago Cove · $1,999,900 · 3 bd/2 ba · 1,765 sq ft
  25. 7450 Wynnewood Square #189 · $170,000 · 2 bd/2.5 ba · 1,031 sq ft
  26. 922 N Pennsylvania Avenue · $1,795,000 · 4 bd/4 ba · 3,440 sq ft
  27. 250 Killarney · $1,600,000 · 4 bd/3.5 ba · 2,568 sq ft
  28. 1418 Lone Feather Trail · $699,500 · 4 bd/2.5 ba · 2,197 sq ft
  29. 462 W Lyman Avenue · $1,450,000 · 3 bd/2.5 ba · 1,944 sq ft
  30. 2450 Grand Teton Circle #2450 · $250,000 · 3 bd/2 ba · 1,311 sq ft
  31. 2228 Howard Drive · $2,460,000 · 4 bd/3.5 ba · 3,294 sq ft · Pending
  32. 1138 S Pennsylvania Avenue · $925,000 · 3 bd/3 ba · 2,434 sq ft
  33. 1946 Strathaven Road · $599,000 · 4 bd/3 ba · 2,102 sq ft · Pending
  34. 1564 Lawndale Circle · $424,900 · 4 bd/2.5 ba · 1,980 sq ft
  35. 5184 Lazy Oaks Drive · $268,000 · 2 bd/2 ba · 1,008 sq ft
  36. 2305 Sun Valley Cir · $279,900 · 2 bd/2 ba · 1,295 sq ft
  37. 1581 Magnolia Ave · $1,425,000 · 4 bd/4 ba · 2,642 sq ft
  38. 1000 S Semoran Boulevard #408 · $138,000 · 1 bd/1 ba · 776 sq ft
  39. 1000 S Semoran Boulevard #306 · $138,000 · 1 bd/1 ba · 796 sq ft
  40. 1000 S Semoran Boulevard #404 · $138,000 · 1 bd/1 ba · 776 sq ft
  41. 2228 Azalea Place · $5,600,000 · 5 bd/5.5 ba · 5,152 sq ft
  42. 609 S Phelps Avenue · $2,800,000 · 5 bd/4.5 ba · 4,018 sq ft
  43. 3006 Northwood Boulevard · $899,000 · 4 bd/3 ba · 2,075 sq ft
  44. 981 Aragon Avenue · $489,000 · 2 bd/1 ba · 857 sq ft
  45. 660 W Morse Boulevard · $2,695,000 · 3 bd/3.5 ba · 3,286 sq ft
  46. 1840 Aster Drive · $374,900 · 3 bd/2 ba · 1,666 sq ft
  47. 2712 Tortoise Cv · $230,000 · 2 bd/1 ba · 924 sq ft
  48. 7488 Whisperwood Drive #28 · $210,000 · 2 bd/2.5 ba · 1,578 sq ft
  49. 240 N Phelps Avenue · $1,999,900 · 5 bd/4.5 ba · 2,889 sq ft
  50. 512 W Swoope Avenue · $1,399,000 · 3 bd/2.5 ba · 2,585 sq ft
  51. 2015 Summerfield Road · $1,250,000 · 4 bd/4 ba · 2,916 sq ft
  52. 1500 Gay Road #3C · $235,000 · 2 bd/2 ba · 1,026 sq ft
  53. 151 North Orlando Avenue #142 · $199,900 · 1 bd/1 ba · 582 sq ft
  54. 101 S New York Avenue #311 · $1,775,000 · 3 bd/3.5 ba · 3,112 sq ft
  55. 1605 Puritan Avenue · $374,000 · 3 bd/2 ba · 1,285 sq ft
  56. 2008 Houndslake Drive · $470,000 · 4 bd/2 ba · 2,250 sq ft
  57. 437 N Capen Avenue · $849,000 · 3 bd/2.5 ba · 1,904 sq ft
  58. 1316 Blue Stem Lane · $725,000 · 4 bd/2.5 ba · 2,196 sq ft
  59. 8433 Commander Cove · $455,000 · 4 bd/2.5 ba · 1,903 sq ft
  60. 723 Symonds Avenue · $1,600,000 · 4 bd/4 ba · 3,065 sq ft
  61. 1265 Arlington Pl · $774,900 · 3 bd/3.5 ba · 2,030 sq ft
  62. 1535 Lawndale Circle · $415,000 · 3 bd/2 ba · 1,676 sq ft
  63. 231 Chelton Circle · $4,500,000 · 4 bd/6 ba · 5,550 sq ft
  64. 1473 Berkshire Avenue · $1,369,000 · 5 bd/4 ba · 2,446 sq ft
  65. 2500 Lee Road #220 · $199,900 · 2 bd/1 ba · 851 sq ft
  66. 641 Northwood Circle · $1,499,000 · 3 bd/4 ba · 2,756 sq ft
  67. 413 W Morse Boulevard · $2,625,000 · 3 bd/3.5 ba · 3,048 sq ft
  68. 2240 Venetian Way · $3,500,000 · 4 bd/3.5 ba · 4,036 sq ft
  69. 1250 Formosa Avenue · $535,000 · 3 bd/3.5 ba · 1,937 sq ft
  70. 5503 Albert Drive · $399,900 · 3 bd/2 ba · 1,366 sq ft
  71. 1404 Border Drive · $998,000 · 4 bd/4 ba · 2,469 sq ft
  72. 715 S Ranger Boulevard · $695,000 · 4 bd/3 ba · 2,312 sq ft
  73. 338 Blue Heron Drive · $836,000 · 3 bd/3 ba · 2,017 sq ft
  74. 1571 Woodland Avenue · $6,000,000 · 5 bd/7 ba · 7,397 sq ft
  75. 1695 Lee Road #D211 · $99,900 · 2 bd/1 ba · 881 sq ft
  76. 1448 Lake Florence Way · $999,900 · 5 bd/4.5 ba · 3,652 sq ft
  77. 300 Carolina Avenue #402C · $650,000 · 3 bd/2 ba · 1,350 sq ft
  78. 1320 Gladiolas Dr · $449,000 · 4 bd/2 ba · 1,624 sq ft
  79. 1570 Palmer Avenue · $1,485,000 · 4 bd/3.5 ba · 3,048 sq ft
  80. 7522 Aloma Pines Court · $375,000 · 3 bd/2.5 ba · 1,872 sq ft
  81. 193 Lewfield Circle · $246,400 · 2 bd/2.5 ba · 1,300 sq ft
  82. 616 Brechin Drive · $999,000 · 4 bd/4.5 ba · 2,638 sq ft
  83. 700 Melrose Avenue #J24 · $350,000 · 1 bd/1 ba · 987 sq ft
  84. 938 Enclave Place · $2,300,000 · 5 bd/4.5 ba · 3,865 sq ft
  85. 1995 Canny Cove · $399,000 · 3 bd/2.5 ba · 1,907 sq ft
  86. 7393 Grand Avenue · $325,000 · 3 bd/2 ba · 1,518 sq ft
  87. 930 Enclave Place · $2,275,000 · 5 bd/4.5 ba · 3,813 sq ft
  88. 1741 Westchester Avenue · $524,900 · 3 bd/2 ba · 1,434 sq ft
  89. 450 Lakewood Drive · $2,500,000 · 5 bd/5 ba · 4,572 sq ft
  90. 446 Melrose Avenue · $1,495,000 · 4 bd/2 ba · 2,640 sq ft
  91. 5143 Lazy Oaks Drive #5143 · $275,000 · 2 bd/2 ba · 1,008 sq ft · Pending
  92. 950 Hanover Avenue · $439,000 · 3 bd/2 ba · 1,606 sq ft
  93. 102 Bell Place · $1,299,000 · 4 bd/3.5 ba · 2,459 sq ft
  94. 2918 Antique Oaks Circle #25 · $189,000 · 2 bd/2 ba · 1,018 sq ft
  95. 541 W Canton Avenue · $2,495,000 · 4 bd/3.5 ba · 3,553 sq ft
  96. 2600 Euston Road · $630,000 · 6 bd/3 ba · 3,145 sq ft
  97. 1441 Cardinal Court · $3,600,000 · 4 bd/5.5 ba · 4,066 sq ft
  98. 7454 Wynnewood Square #188 · $229,000 · 3 bd/2.5 ba · 1,151 sq ft
  99. 3021 Aaron Burr Avenue #3 · $140,000 · 2 bd/2.5 ba · 1,090 sq ft
  100. 630 Killarney Bay Court #3 · $449,900 · 2 bd/2.5 ba · 1,428 sq ft
  101. 1131 Wildmeadow Run · $825,000 · 4 bd/3.5 ba · 2,589 sq ft
  102. 914 Enclave Place · $2,070,000 · 5 bd/4.5 ba · 3,617 sq ft
  103. 905 Enclave Place · $1,550,000 · 4 bd/3.5 ba · 2,756 sq ft
  104. 901 Enclave Place · $1,550,000 · 4 bd/3.5 ba · 2,738 sq ft
  105. 501 Heritage Boulevard · $419,000 · 4 bd/2 ba · 1,376 sq ft
  106. 1260 Alabama Drive · $6,900,000 · 6 bd/6 ba · 6,396 sq ft
  107. 1113 Via Del Mar · $1,595,000 · 3 bd/2 ba · 2,012 sq ft
  108. 1927 Eland Avenue · $799,000 · 5 bd/3 ba · 2,242 sq ft
  109. 330 Elkhorn Court · $509,900 · 3 bd/2 ba · 1,570 sq ft
  110. 2231 Nairn Drive · $499,000 · 3 bd/2 ba · 1,088 sq ft
  111. 230 Strathy Lane · $499,000 · 2 bd/1 ba · 920 sq ft
  112. 1751 Goodrich Avenue · $1,380,000 · 4 bd/3.5 ba · 2,170 sq ft
  113. 432 W Swoope Avenue · $680,000 · 4 bd/3.5 ba · 2,664 sq ft
  114. 2217 Sussex Road · $485,000 · 4 bd/2 ba · 2,092 sq ft
  115. 1840 Anzle Avenue · $1,750,000 · 4 bd/2.5 ba · 2,350 sq ft
  116. 151 N Orlando Avenue #118 · $299,999 · 2 bd/1 ba · 710 sq ft
  117. 1885 Temple Drive · $2,195,000 · 5 bd/3.5 ba · 3,691 sq ft
  118. 2500 Lee Rd. #222 · $184,400 · 1 bd/1 ba · 645 sq ft
  119. 560 Ololu Drive · $849,000 · 2 bd/2 ba · 1,086 sq ft
  120. 151 N Orlando Avenue ##115 · $285,000 · 2 bd/1 ba · 710 sq ft
  121. 311 Scottsdale Square #311 · $109,000 · 1 bd/1 ba · 785 sq ft
  122. 3370 Cedar Springs Place #156 · $179,990 · 2 bd/2.5 ba · 1,031 sq ft
  123. 2336 Sun Valley Circle #Bldg 20 · $285,000 · 2 bd/2 ba · 1,669 sq ft
  124. 1821 Englewood Road · $2,950,000 · 5 bd/5.5 ba · 3,863 sq ft
  125. 2758 Banchory Road · $619,500 · 3 bd/2.5 ba · 1,539 sq ft
  126. 311 E Morse Boulevard #7-11 · $279,000 · 1 bd/1 ba · 570 sq ft
  127. 3071 George Mason Avenue #5 · $89,900/1 ba · 549 sq ft
  128. 1695 Lee Road #C202 · $205,000 · 3 bd/2 ba · 1,149 sq ft
  129. 470 W Comstock Avenue · $5,480,000 · 6 bd/6.5 ba · 6,134 sq ft
  130. 2718 Eastern Parkway · $2,450,000 · 4 bd/4.5 ba · 3,308 sq ft
  131. 1824 Jessica Court · $1,149,000 · 4 bd/2.5 ba · 2,582 sq ft
  132. 1386 Clematis Lane · $417,000 · 4 bd/3 ba · 1,714 sq ft
  133. 3471 Athena Drive · $389,000 · 3 bd/2 ba · 1,416 sq ft
  134. 220 Killarney Bay Court #6-2 · $339,000 · 2 bd/2 ba · 1,140 sq ft

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

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