Buying or selling? Call (904) 351-6461

All Homes for Sale in Winter Park, FL

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.

Page 1 · Page 2 · Page 3 ·

  1. 2812 Mulford Avenue · $2,495,000 · 5 bd/5.5 ba · 3,656 sq ft
  2. 1641 Hibiscus Avenue · $1,725,000 · 4 bd/4 ba · 3,594 sq ft
  3. 2370 Barbados Drive · $305,000 · 3 bd/2 ba · 1,467 sq ft
  4. 1398 Grove Terrace · $1,949,000 · 4 bd/3.5 ba · 3,450 sq ft
  5. 775 Mcintyre Avenue #9 · $849,999 · 3 bd/2.5 ba · 2,052 sq ft
  6. 1261 Michigan Avenue · $650,000 · 3 bd/2.5 ba · 1,798 sq ft
  7. 2535 Leeward Way · $325,000 · 3 bd/2 ba · 1,783 sq ft
  8. 304 Santiago Drive · $2,195,000 · 5 bd/4.5 ba · 4,213 sq ft
  9. 1552 Little Wren Lane · $440,000 · 3 bd/2.5 ba · 2,308 sq ft
  10. 1441 Palm Avenue · $2,449,000 · 5 bd/4.5 ba · 3,391 sq ft
  11. 2237 Woodcrest Drive · $1,425,000 · 4 bd/4.5 ba · 3,563 sq ft
  12. 1534 Miller Avenue · $1,379,900 · 4 bd/3.5 ba · 2,984 sq ft
  13. 2011 Harmon Avenue · $849,900 · 4 bd/3 ba · 2,434 sq ft
  14. 1935 Azalea Avenue · $410,000 · 3 bd/2 ba · 1,300 sq ft
  15. 7361 Grand Avenue · $385,000 · 3 bd/2 ba · 1,305 sq ft
  16. 4940 Tangerine Avenue #4940 · $249,000 · 3 bd/2 ba · 1,345 sq ft
  17. 3462 Seagrape Drive · $225,000 · 3 bd/1 ba · 1,227 sq ft
  18. 200 St Andrews Boulevard #906 · $175,000 · 1 bd/1 ba · 727 sq ft
  19. 1441 Grove Terrace · $5,950,000 · 5 bd/6 ba · 5,796 sq ft
  20. 125 S Interlachen Avenue #4 · $3,995,000 · 3 bd/4 ba · 3,885 sq ft
  21. 1900 Sunset Drive · $1,650,000 · 4 bd/3.5 ba · 2,754 sq ft
  22. 345 Beloit Avenue · $1,625,000 · 3 bd/2.5 ba · 2,884 sq ft
  23. 1500 Harris Circle · $1,175,000 · 3 bd/3 ba · 2,096 sq ft
  24. 346 Elkhorn Court · $575,000 · 4 bd/2 ba · 1,891 sq ft · Pending
  25. 1931 Aster Drive · $575,000 · 3 bd/2.5 ba · 2,031 sq ft · Pending
  26. 257 Lincolnshire Road · $550,000 · 3 bd/2 ba · 1,610 sq ft
  27. 7536 Village Green Drive · $479,900 · 3 bd/2 ba · 1,647 sq ft
  28. 1825 Chilean Lane · $450,000 · 5 bd/3 ba · 1,636 sq ft
  29. 2038 Ponderosa Avenue · $415,000 · 3 bd/2 ba · 1,360 sq ft
  30. 3027 Aaron Bur Avenue #L1 · $169,999 · 2 bd/2.5 ba · 1,090 sq ft
  31. 1225 Sharon Place · $1,749,000 · 5 bd/3.5 ba · 3,097 sq ft · Pending
  32. 1350 Lyndale Boulevard · $1,499,000 · 4 bd/3.5 ba · 3,478 sq ft
  33. 2825 Mulford Avenue · $629,000 · 2 bd/2 ba · 1,249 sq ft
  34. 510 Fitzwalter Drive · $530,000 · 3 bd/2 ba · 1,385 sq ft
  35. 2356 Shadowland Loop · $460,000 · 3 bd/2.5 ba · 2,076 sq ft
  36. 700 Melrose Avenue #A22 · $325,000 · 2 bd/2 ba · 1,074 sq ft
  37. 2352 Sun Valley Circle · $280,000 · 2 bd/2 ba · 1,495 sq ft
  38. 640 N Park Avenue #3 · $745,000 · 2 bd/1.5 ba · 897 sq ft
  39. 1401 Pelham Road · $650,000 · 3 bd/2 ba · 1,594 sq ft
  40. 624 Dunraven Drive · $620,000 · 3 bd/2 ba · 1,762 sq ft
  41. 5334 Lanyard Court · $479,900 · 3 bd/2 ba · 1,561 sq ft
  42. 239 Orange Terrace Drive · $450,000 · 4 bd/2.5 ba · 1,866 sq ft
  43. 506 Lander Road · $450,000 · 3 bd/2 ba · 1,346 sq ft
  44. 1021 Princess Gate Boulevard · $410,000 · 3 bd/2 ba · 1,318 sq ft
  45. 1830 Gladiolas Drive · $375,000 · 3 bd/2 ba · 1,674 sq ft
  46. 2168 Ridge Drive · $365,000 · 3 bd/2 ba · 1,208 sq ft
  47. 1200 Via Salerno · $5,995,000 · 5 bd/5.5 ba · 5,476 sq ft
  48. 541 Virginia Drive · $5,695,000 · 4 bd/3.5 ba · 4,725 sq ft
  49. 1355 Hibiscus Avenue · $2,100,000 · 5 bd/5.5 ba · 4,155 sq ft
  50. 1940 Magnolia Avenue · $1,190,000 · 4 bd/3.5 ba · 5,519 sq ft
  51. 1735 Demetree Drive · $1,050,000 · 4 bd/3 ba · 2,787 sq ft
  52. 170 Balfour Drive #1 · $299,000 · 2 bd/2 ba · 1,032 sq ft
  53. 7463 Canford Court #15 · $270,000 · 3 bd/2.5 ba · 1,580 sq ft
  54. 2330 Westminster Ct. · $985,000 · 5 bd/3 ba · 3,296 sq ft
  55. 870 N Phelps Avenue · $850,000 · 4 bd/3 ba · 2,301 sq ft
  56. 1462 Siciliano Point · $325,000 · 3 bd/2.5 ba · 1,628 sq ft
  57. 623 Grenadine Court #623 · $199,900 · 2 bd/2 ba · 1,037 sq ft
  58. 1631 Hillcrest Avenue · $4,500,000 · 5 bd/5.5 ba · 4,754 sq ft
  59. 1884 Jessica Court · $699,900 · 3 bd/2 ba · 1,666 sq ft
  60. 1458 Lone Feather Trail · $650,000 · 4 bd/2.5 ba · 1,770 sq ft
  61. 808 Densmore Drive · $509,999 · 3 bd/2 ba · 1,460 sq ft
  62. 603 Carnation Drive · $419,900 · 4 bd/2 ba · 1,427 sq ft
  63. 4832 Tangerine Avenue #4832 · $188,800 · 2 bd/2 ba · 1,058 sq ft
  64. 1825 Whitehall Drive · $3,195,000 · 4 bd/5 ba · 4,311 sq ft
  65. 1211 Schultz Avenue · $475,000 · 3 bd/2 ba · 1,085 sq ft
  66. 4786 Tangerine Avenue #4786 · $220,000 · 2 bd/1.5 ba · 1,281 sq ft
  67. 2887 Temple Trail · $695,000 · 2 bd/2.5 ba · 1,801 sq ft
  68. 565 Huntington Avenue #565 · $635,000 · 3 bd/2.5 ba · 2,015 sq ft
  69. 7640 Village Green Dr · $439,000 · 3 bd/2 ba · 1,631 sq ft
  70. 5405 Justine Way · $399,900 · 3 bd/2 ba · 1,247 sq ft
  71. 5468 Bracken Court · $299,000 · 3 bd/2.5 ba · 1,602 sq ft
  72. 617 N Interlachen Avenue · $4,695,000 · 11 bd/7.5 ba · 3,615 sq ft
  73. 1600 Legion Drive · $3,495,000 · 5 bd/5.5 ba · 4,483 sq ft
  74. 1681 Woodland Avenue · $2,629,000 · 5 bd/4.5 ba · 3,682 sq ft
  75. 2501 Lafayette Avenue · $1,795,000 · 4 bd/4 ba · 2,819 sq ft · Pending
  76. 148 Oak Grove Rd · $320,000 · 3 bd/2 ba · 1,156 sq ft
  77. 1939 Woodcrest Drive · $1,349,000 · 4 bd/3.5 ba · 2,575 sq ft
  78. 8061 Pleasant Pine Circle · $750,000 · 5 bd/3.5 ba · 3,496 sq ft
  79. 2640 Beverly Avenue · $305,000 · 3 bd/1 ba · 1,216 sq ft
  80. 1915 Carrigan Avenue · $299,900 · 3 bd/1 ba · 1,520 sq ft · Pending
  81. 1011 Mckean Circle · $6,000,000 · 5 bd/6 ba · 4,806 sq ft
  82. 952 Moss Lane · $1,319,950 · 4 bd/3.5 ba · 3,474 sq ft
  83. 1445 Via Sangro Place · $1,249,000 · 6 bd/5.5 ba · 5,021 sq ft
  84. 1411 Devon Road · $950,000 · 2 bd/2 ba · 1,947 sq ft
  85. 216 Lewfield Cir #216 · $230,000 · 3 bd/2 ba · 1,268 sq ft
  86. 200 Saint Andrews Boulevard #3408 · $170,000 · 1 bd/1 ba · 793 sq ft
  87. 1751 Glencoe Road · $3,390,000 · 5 bd/6 ba · 4,520 sq ft
  88. 1399 Aloma Avenue · $575,000 · 3 bd/2 ba · 1,804 sq ft
  89. 2219 Winter Woods Boulevard · $479,999 · 3 bd/2.5 ba · 1,776 sq ft
  90. 1611 Chestnut Avenue · $985,000 · 4 bd/4 ba · 2,916 sq ft
  91. 1407 Broad Wing Lane · $482,000 · 3 bd/2.5 ba · 2,308 sq ft
  92. 2189 Sussex Road · $375,000 · 4 bd/2.5 ba · 1,776 sq ft
  93. 1740 Puritan Avenue · $314,000 · 3 bd/2 ba · 1,229 sq ft
  94. 1760 Oakhurst Avenue · $2,500,000 · 5 bd/4.5 ba · 3,700 sq ft
  95. 3020 Antique Oaks Circle #129 · $135,000 · 2 bd/2 ba · 1,018 sq ft · Pending
  96. 1737 Indiana Avenue · $1,399,900 · 4 bd/3.5 ba · 2,984 sq ft
  97. 351 Starling Road · $499,900 · 3 bd/1.5 ba · 1,979 sq ft
  98. 2126 Albert Lee Parkway · $415,000 · 3 bd/2 ba · 1,187 sq ft
  99. 500 N Pennsylvania Avenue #G · $349,500 · 2 bd/1 ba · 709 sq ft
  100. 731 Bongart Road · $519,900 · 4 bd/3 ba · 1,842 sq ft
  101. 4882 Tangerine Avenue #4882 · $185,000 · 2 bd/1.5 ba · 1,281 sq ft
  102. 2823 Parkland Circle · $3,250,000 · 5 bd/6 ba · 4,459 sq ft
  103. 2228 King Charles Court · $575,000 · 4 bd/3 ba · 2,551 sq ft
  104. 2020 Leanne Court · $469,900 · 4 bd/3 ba · 2,088 sq ft
  105. 700 Melrose Avenue #M23 · $340,000 · 2 bd/2 ba · 1,074 sq ft
  106. 1500 Gay Road #26-C · $255,000 · 2 bd/2 ba · 1,026 sq ft
  107. 1602 Alabama Drive #107 · $1,150,000 · 2 bd/2 ba · 993 sq ft
  108. 3307 Amber Wood Way #106 · $169,000 · 2 bd/2.5 ba · 1,031 sq ft
  109. 645 Pansy Avenue · $2,390,000 · 4 bd/4.5 ba · 3,661 sq ft
  110. 2613 Lafayette Avenue · $1,699,900 · 4 bd/3.5 ba · 2,661 sq ft
  111. 112 Bell Place · $575,000 · 3 bd/2 ba · 2,253 sq ft
  112. 2052 Wood Thrush Lane · $900,000 · 4 bd/3 ba · 2,807 sq ft
  113. 2322 Woodcrest Drive · $650,000 · 4 bd/2 ba · 1,650 sq ft
  114. 2067 Poinciana Road · $548,000 · 4 bd/2 ba · 2,352 sq ft
  115. 310 Granada Drive · $325,000 · 3 bd/2 ba · 1,344 sq ft
  116. 3032 Antique Oaks Circle #145 · $134,999 · 1 bd/1 ba · 749 sq ft
  117. 518 Gilbert Road · $649,000 · 3 bd/2 ba · 1,573 sq ft
  118. 918 Enclave Place · $2,125,000 · 5 bd/4.5 ba · 3,713 sq ft
  119. 2500 Lee Road #123 · $159,900 · 1 bd/1 ba · 645 sq ft
  120. 302 Lewfield Circle #302 · $140,000 · 1 bd/1 ba · 678 sq ft
  121. 2119 Howard Drive · $3,195,000 · 5 bd/5.5 ba · 4,139 sq ft
  122. 100 S Interlachen Avenue #401 · $825,000 · 3 bd/2 ba · 1,639 sq ft
  123. 7560 Aloma Pines Court · $325,000 · 3 bd/2.5 ba · 1,866 sq ft
  124. 188 Sandlewood #1 · $290,000 · 2 bd/2.5 ba · 1,133 sq ft
  125. 2657 Exuma Way · $285,000 · 3 bd/2 ba · 1,467 sq ft
  126. 712 Baffie Avenue · $419,900 · 3 bd/1 ba · 1,304 sq ft
  127. 200 Saint Andrews Boulevard #704 · $159,000 · 1 bd/1 ba · 793 sq ft
  128. 2007 Edwin Boulevard · $1,995,000 · 4 bd/3.5 ba · 3,314 sq ft
  129. 513 Dunraven Drive · $1,950,000 · 5 bd/4.5 ba · 3,560 sq ft
  130. 7498 Aloma Pines Court · $355,000 · 3 bd/2.5 ba · 1,872 sq ft
  131. 266 N Ranger Boulevard · $724,900 · 4 bd/3 ba · 1,692 sq ft
  132. 7786 Fox Knoll Place · $398,000 · 3 bd/2 ba · 1,301 sq ft
  133. 1306 S Pennsylvania Avenue #5 · $347,500 · 2 bd/1 ba · 830 sq ft
  134. 2345 Brookshire Avenue · $825,000 · 3 bd/3 ba · 2,488 sq ft
  135. 1695 Lee Road #C206 · $140,000 · 2 bd/1 ba · 881 sq ft

Page 1 · Page 2 · Page 3 ·

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

Hiring an agent in Winter Park, FL?

Get matched with the right local expert.

Tell us your goal in Winter Park, FL and we’ll connect you with the Momentum agent who knows it best — backed by a RealTrends 500 brokerage. No pressure, no obligation.

Prefer to talk now? Call (904) 351-6461.

Work with a local Winter Park, FL expert

A real conversation with a local specialist, usually within one business day.

or call (904) 351-6461