All Homes for Sale in Cudjoe Key, FL

Every home for sale in Cudjoe Key, FL from the live MLS: 50 listings, newest first, 200 per page. Back to the Cudjoe Key homes for sale hub for prices by ZIP, property type and community.

1. 701 Spanish Main Drive #Lot 62 · $225,000 · 2 bd/1 ba
2. 701 Spanish Main Drive #198 · $949,600 · 2 bd/2 ba
3. 165 Colson Drive · $1,645,000 · 3 bd/2 ba
4. 701 Spanish Main Drive #321 · $799,000 · 2 bd/2 ba
5. 22960 Sharp Lane · $525,000 · 2 bd/1 ba
6. 701 Spanish Main Drive #455 · $399,999 · 1 bd/1 ba
7. 20731 W 2Nd Avenue · $3,200,000 · 5 bd/4 ba
8. 459 Pattison Drive · $2,299,995 · 3 bd/2 ba
9. 22832 John Silver Lane · $849,000 · 3 bd/3 ba
10. 111 Doubloon Lane · $850,000 · 2 bd/2 ba
11. 701 Spanish Main Drive #123 · $674,999 · 2 bd/2 ba
12. 701 Spanish Main Drive #171 · $799,000 · 2 bd/2 ba
13. 1106 Thatch Lane · $1,999,000 · 4 bd/3.5 ba
14. 22968 Drake Lane · $819,500 · 3 bd/2 ba
15. 22970 Gasparilla Lane · $1,799,000 · 3 bd/2 ba
16. 23057 Bluegill Lane · $1,349,000 · 3 bd/2 ba
17. 701 Spanish Main Drive #533 · $239,000 · 1 bd/1 ba
18. 94 Sacarma Drive · $2,060,000 · 5 bd/3 ba
19. 701 Spanish Main Drive #246 · $444,999 · 1 bd/1 ba
20. 342 Spanish Main Drive · $949,000 · 3 bd/2 ba
21. 125 Colson Drive · $2,195,000 · 5 bd/3 ba
22. 701 Spanish Main Drive #424 · $549,000 · 2 bd/2 ba
23. 21640 Overseas Highway · $2,800,000 · 4 bd/3 ba · Pending
24. 20833 W 4Th Avenue · $2,699,999 · 4 bd/2.5 ba
25. 21470 Overseas Highway · $5,750,000 · 13 bd/7 ba
26. 174 Tortuga Lane · $1,270,000 · 3 bd/2 ba
27. 22822 Buccaneer Lane · $799,000 · 2 bd/2 ba
28. 701 Spanish Main Drive #659 · $487,000 · 2 bd/2 ba
29. 21023 2Nd Avenue · $2,499,000 · 4 bd/2 ba
30. 701 Spanish Main Drive #639 · $425,000 · 2 bd/1 ba
31. 135 Tortuga Lane · $895,000 · 3 bd/2 ba
32. 116 Spanish Main Drive · $1,269,000 · 2 bd/2 ba
33. 22939 Gasparilla Lane · $1,399,000 · 3 bd/2 ba
34. 21090 5Th Avenue · $3,099,000 · 4 bd/3 ba
35. 22542 Jolly Roger Drive · $1,725,000 · 4 bd/3 ba
36. 20868 W 5Th Avenue · $1,150,000 · 2 bd/2 ba
37. 701 Spanish Main Drive #140 · $399,900 · 2 bd/1 ba
38. 21025 3Rd Avenue · $1,299,000 · 3 bd/2 ba
39. 22978 Port Royal Lane · $875,000 · 2 bd/1 ba
40. 701 Spanish Main Drive #423 · $267,000 · 1 bd/1 ba
41. 701 Spanish Main Drive #417 · $493,000 · 2 bd/2 ba · Pending
42. 701 Spanish Main Drive #604 · $595,000 · 2 bd/2 ba
43. 20920 5Th Avenue · $2,795,000 · 4 bd/3 ba
44. 51 Sawyer Drive · $1,799,000 · 3 bd/2.5 ba
45. 51 Drost Drive · $1,399,000 · 3 bd/2 ba
46. 701 Spanish Main Drive #265 · $879,000 · 2 bd/2 ba
47. 701 Spanish Main Drive #566 · $320,000 · 2 bd/1 ba
48. 701 Spanish Main Drive #247 · $535,000 · 2 bd/2 ba
49. 701 Spanish Main Drive #182 · $485,000 · 1 bd/1 ba
50. 21540 21470 Overseas Highway · $12,999,999 · 31 bd/19 ba

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