All Homes for Sale in Osprey, FL

Every home for sale in Osprey, FL from the live MLS: 104 listings, newest first, 200 per page. Back to the Osprey homes for sale hub for prices by ZIP, property type and community.

1. 854 Macewen Drive · $3,670,000 · 4 bd/5 ba · 9,081 sq ft
2. 447 E Macewen Drive · $2,750,000 · 4 bd/4.5 ba · 5,323 sq ft · Pending
3. 794 Lytham Circle · $2,600,000 · 4 bd/4 ba · 4,450 sq ft · Pending
4. 222 Saint James Park · $1,800,000 · 3 bd/3.5 ba · 3,665 sq ft · Pending
5. 401 N Point Road #701 · $1,480,000 · 3 bd/3 ba · 2,594 sq ft · Pending
6. 401 N Point Road #903 · $1,250,000 · 3 bd/3 ba · 2,203 sq ft · Pending
7. 256 Turquoise Lane · $995,000 · 3 bd/2 ba · 2,351 sq ft · Pending
8. 570 Blackburn Point Road #Siesta 25 · $149,900
9. 275 Lookout Point Drive · $4,590,000 · 5 bd/5 ba · 5,279 sq ft
10. 650 Oaks Creek Court · $3,700,000 · 4 bd/4 ba · 4,314 sq ft
11. 385 North Point Road #701 · $1,399,000 · 3 bd/3 ba · 2,594 sq ft
12. 401 N Point Road #703 · $1,200,000 · 3 bd/3 ba · 2,203 sq ft
13. 102 Windward Drive · $1,047,000 · 3 bd/2.5 ba · 2,134 sq ft
14. 401 N Point Road #404 · $1,025,000 · 3 bd/3 ba · 2,778 sq ft
15. 155 Sea Anchor Drive · $895,000 · 3 bd/3 ba · 2,683 sq ft · Pending
16. 385 N Point Road #401 · $695,000 · 3 bd/3 ba · 2,594 sq ft
17. 130 Willow Bend Way · $669,900 · 4 bd/3 ba · 2,683 sq ft · Pending
18. 700 Shadow Bay Way · $655,000 · 3 bd/2.5 ba · 2,792 sq ft
19. 3603 N Point Road #202 · $629,400 · 3 bd/3 ba · 3,147 sq ft
20. 1346 Thornapple Drive · $540,000 · 3 bd/2 ba · 2,248 sq ft
21. 145 Edgewood Drive · $175,000 · 2 bd/2 ba · 960 sq ft
22. 23 Siesta Circle · $165,000 · 2 bd/2 ba · 924 sq ft
23. 570 Blackburn Point Road #36 · $99,500
24. 141 Sugar Mill Drive · $1,700,000 · 3 bd/3 ba · 3,118 sq ft
25. 649 Crane Prairie Way · $639,000 · 3 bd/3 ba · 2,222 sq ft
26. 1140 Beachcomber Court #11 · $540,000 · 3 bd/2.5 ba · 2,040 sq ft
27. 1216 N Casey Key Road · $9,750,000 · 5 bd/7 ba · 8,050 sq ft
28. 1819 Highland Road · $319,000 · 2 bd/2.5 ba · 1,240 sq ft
29. 385 N Point Road #301 · $750,000 · 3 bd/3 ba · 2,594 sq ft · Pending
30. 1104 Mallard Marsh Drive · $799,000 · 3 bd/2.5 ba · 2,678 sq ft
31. 401 N Point Road #303 · $445,000 · 3 bd/3 ba · 2,203 sq ft · Pending
32. 717 Pine Run Dr. #717 · $159,900 · 1 bd/1 ba · 586 sq ft
33. 120 Villa Drive #120 · $465,000 · 2 bd/2 ba · 1,404 sq ft
34. 296 Pine Ranch Trail · $1,100,000 · 5 bd/3.5 ba · 3,354 sq ft
35. 3621 N Point Road #403 · $700,000 · 3 bd/3 ba · 2,680 sq ft
36. 586 Oak Bay Drive · $649,000 · 3 bd/2 ba · 2,084 sq ft
37. 250 Hidden Bay Drive #302 · $625,000 · 3 bd/2 ba · 1,937 sq ft
38. 7303 Jessie Harbor Drive #7303 · $449,000 · 3 bd/2 ba · 1,883 sq ft
39. 409 N Point Road #803 · $985,000 · 3 bd/3 ba · 2,203 sq ft
40. 109 Woodland Place · $244,900 · 2 bd/2 ba · 1,223 sq ft
41. 17 Bayhead Lane · $1,270,000 · 3 bd/2 ba · 2,850 sq ft
42. 226 Saint James Park · $1,495,000 · 3 bd/2.5 ba · 2,591 sq ft
43. 51 Macewen Drive #5 · $235,000 · 1 bd/1 ba · 595 sq ft
44. 210 Patterson Avenue · $950,000 · 3 bd/1.5 ba · 2,084 sq ft
45. 1328 Thornapple Drive · $749,900 · 3 bd/2 ba · 2,174 sq ft
46. 1036 Oak Meadow Lane · $630,000 · 4 bd/2 ba · 2,186 sq ft
47. 154 Lookout Point Drive · $2,095,000 · 4 bd/3.5 ba · 4,578 sq ft
48. 264 Woods Point Road #264 · $695,000 · 3 bd/3 ba · 2,837 sq ft
49. 583 Pine Ranch East Road · $529,000 · 4 bd/2 ba · 2,203 sq ft
50. 547 Meadow Sweet Circle · $550,000 · 3 bd/2 ba · 1,731 sq ft · Pending
51. 1417 Landview Lane · $1,349,999 · 4 bd/4 ba · 3,255 sq ft
52. 2046 Cordes Street · $565,000 · 3 bd/2 ba · 1,705 sq ft
53. 907 Eagle Isle Court · $1,100,000 · 4 bd/3 ba · 3,984 sq ft
54. 5100 Jessie Harbor Drive #404 · $599,000 · 2 bd/2 ba · 2,143 sq ft
55. 7204 Jessie Harbor Drive #7204 · $395,000 · 2 bd/2 ba · 1,255 sq ft
56. 570 Blackburn Point Road #23 · $89,000
57. 701 Pine Run Drive #701 · $151,000 · 1 bd/1 ba · 586 sq ft · Pending
58. 329 Bay Vista Avenue · $399,000 · 2 bd/2 ba · 1,346 sq ft
59. 260 Hidden Bay Drive #402 · $775,000 · 3 bd/2.5 ba · 1,950 sq ft
60. 780 Sarabay Road #16 · $425,000 · 2 bd/2 ba · 1,574 sq ft
61. 110 Woodland Place #110 · $215,000 · 2 bd/2 ba · 1,325 sq ft
62. 320 Tropic Drive · $185,000 · 2 bd/2 ba · 1,199 sq ft
63. 1495 Landview Lane · $760,000 · 3 bd/2 ba · 2,474 sq ft
64. 2309 Jessie Harbor Drive #2402 · $480,000 · 3 bd/2.5 ba · 2,006 sq ft
65. 206 Four Knot Lane · $1,690,000 · 3 bd/2 ba · 2,411 sq ft
66. 116 Woodland Place #116 · $249,900 · 2 bd/2 ba · 1,325 sq ft
67. 759 Fordingbridge Way · $700,000 · 4 bd/3.5 ba · 2,950 sq ft
68. 4296 Expedition Way #104 · $289,000 · 2 bd/2 ba · 1,135 sq ft
69. 5100 Jessie Harbor Drive #304 · $699,000 · 2 bd/2 ba · 2,143 sq ft
70. 409 North Point Road #401 · $560,000 · 3 bd/3 ba · 2,594 sq ft
71. 4429 Conchfish Lane · $499,999 · 3 bd/2 ba · 2,004 sq ft
72. 280 Hidden Bay Drive #302 · $719,000 · 3 bd/2 ba · 1,937 sq ft
73. 14401 Masthead Drive · $2,850,000 · 3 bd/3.5 ba · 2,665 sq ft
74. 6100 Jessie Harbor Drive #202 · $798,000 · 3 bd/3.5 ba · 3,771 sq ft
75. 4226 Frontier Lane #103 · $299,000 · 2 bd/2 ba · 1,135 sq ft
76. 14021 Bellagio Way #404 · $999,900 · 3 bd/3 ba · 2,187 sq ft
77. 14041 Bellagio Way #214 · $700,000 · 3 bd/2 ba · 1,799 sq ft
78. 570 Blackburn Point Road #26 · $36,000
79. 1527 Buoy Lane · $1,100,000 · 3 bd/2.5 ba · 2,830 sq ft
80. 570 Blackburn Point Road #43 · $115,000
81. 14021 Bellagio Way #309 · $879,000 · 3 bd/2.5 ba · 2,199 sq ft
82. 570 Blackburn Point Road #13 · $109,000
83. 313 Lookout Point Drive · $5,299,999 · 4 bd/4.5 ba · 5,337 sq ft
84. 524 Sarabay Road · $419,000 · 3 bd/2 ba · 1,760 sq ft
85. 3621 N Point Road #301 · $525,000 · 3 bd/3 ba · 2,680 sq ft
86. 401 N Point Road #1001 · $1,995,000 · 3 bd/3 ba · 3,029 sq ft
87. 18 N Casey Key Road · $1,750,000 · 3 bd/2 ba · 1,977 sq ft
88. 385 N Point Road #304 · $1,100,000 · 3 bd/3 ba · 2,778 sq ft
89. 242 Hidden Bay Drive #602 · $700,000 · 2 bd/2 ba · 1,932 sq ft
90. 1811 Highland Road · $409,900 · 2 bd/2 ba · 1,725 sq ft
91. 348 Tropic Drive · $104,900 · 2 bd/2 ba · 864 sq ft
92. 538 Dove Pointe Drive · $1,950,000 · 4 bd/5.5 ba · 4,346 sq ft
93. 570 Blackburn Point Road #11 · $39,500
94. 599 Pine Ranch East Road · $815,000 · 3 bd/2 ba · 2,188 sq ft
95. 1801 Highland Road · $289,900 · 2 bd/2 ba · 1,165 sq ft
96. 21 Bayhead Lane · $789,000 · 3 bd/2 ba · 2,246 sq ft
97. 121 N Casey Key Road · $6,100,000 · 4 bd/5.5 ba · 4,096 sq ft
98. 236 Saint James Park · $2,700,000 · 6 bd/6.5 ba · 6,246 sq ft
99. 110 Pine Avenue · $649,000 · 3 bd/2 ba · 2,058 sq ft
100. 852 Macewen Drive · $2,395,000 · 3 bd/3.5 ba · 4,519 sq ft
101. 385 N Point Road #402 · $615,000 · 3 bd/3 ba · 2,055 sq ft
102. 401 N Point Road #301 · $459,900 · 3 bd/3 ba · 2,594 sq ft
103. 909 Macewen Drive · $1,595,000 · 3 bd/3.5 ba · 4,241 sq ft
104. 409 N Point Road #502 · $575,000 · 3 bd/3 ba · 2,055 sq ft

Updated October 13, 2026. Listing data from the MLS, deemed reliable but not guaranteed.