All Homes for Sale in Summerland Key, FL

Every home for sale in Summerland Key, FL from the live MLS: 26 listings, newest first, 200 per page. Back to the Summerland Key homes for sale hub for prices by ZIP, property type and community.

1. 17287 Cayman Dr Drive #17287 · $7,800 · 3 bd/2 ba
2. 667 E Caribbean Drive · $1,050,000 · 2 bd/2 ba
3. 947 Gulf Drive · $1,559,000 · 3 bd/2 ba
4. 481 E Shore Drive · $5,500,000 · 3 bd/3 ba
5. 24923 Park Drive · $899,000 · 2 bd/1 ba
6. 27 N Lake Drive · $799,000 · 3 bd/1 ba
7. 486 S Airport Drive · $1,300,000 · 2 bd/2 ba
8. 25361 1St Street · $3,500,000 · 3 bd/3 ba
9. 23950 Overseas Highway · $2,799,000 · 5 bd/4 ba
10. 24740 Park Drive · $649,000 · 2 bd/2 ba
11. 361 Avenue D · $3,100,000 · 2 bd/3 ba
12. 23940 Overseas Highway · $899,000 · 3 bd/2 ba
13. 96 John Street · $535,000 · 3 bd/2 ba
14. 0 Howell Key · $16,900,000 · 5 bd/4 ba
15. 466 W Shore Drive · $1,250,000 · 2 bd/2 ba
16. 706 E Caribbean Drive · $1,145,000 · 3 bd/2 ba
17. 848 E Caribbean Drive · $2,246,000 · 3 bd/1.5 ba
18. 414 E Caribbean Drive · $3,495,000 · 4 bd/3.5 ba
19. 637 E Caribbean Drive · $1,100,000 · 2 bd/2 ba
20. 937 Gulf Drive · $2,220,000 · 3 bd/2 ba
21. 24348 Caribbean Drive · $3,295,000 · 3 bd/3 ba
22. 231 E Shore Drive #4 · $4,375,000 · 5 bd/5.5 ba · Pending
23. 231 E Shore Drive #1 · $3,995,900 · 5 bd/5.5 ba · Pending
24. 24840 Park Drive · $950,000 · 3 bd/2 ba
25. 231 E Shore Drive #6 · $4,400,000 · 5 bd/5.5 ba
26. 860 Lagoon Drive · $1,950,000 · 3 bd/3 ba

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