All Homes for Sale in Upper Matecumbe Key Islamorada, FL

Every home for sale in Upper Matecumbe Key Islamorada, FL from the live MLS: 28 listings, newest first, 200 per page. Back to the Upper Matecumbe Key Islamorada homes for sale hub for prices by ZIP, property type and community.

1. 18 Pen Key Club · $3,900,000 · 3 bd/3 ba
2. 154 Carroll Street · $2,699,000 · 4 bd/4 ba
3. 33 Pen Key Club Drive · $2,195,000 · 3 bd/3.5 ba
4. 36 Park Road · $1,495,000 · 4 bd/3 ba
5. 80902 Old Highway · $2,950,000 · 4 bd/3 ba
6. 81250 Overseas Highway # 5 · $2,290,000 · 4 bd/3 ba
7. 80639 Old Highway #204 · $3,195,000 · 4 bd/4.5 ba · Pending
8. 82779 Old Highway #1 · $4,750,000 · 4 bd/4.5 ba
9. 81250 Overseas Highway #2 · $2,485,000 · 3 bd/3 ba
10. 81801 Overseas Highway #716 · $549,500 · 1 bd/1 ba
11. 81801 Overseas Highway #715 · $549,500 · 1 bd/1 ba
12. 81801 Old Highway #754 · $649,000 · 1 bd/1 ba
13. 19 Avacado Street · $13,750,000 · 5 bd/6 ba
14. 143 N Hammock Road · $1,199,000 · 3 bd/3 ba
15. 81801 Overseas Highway #637 · $715,000 · 1 bd/1 ba
16. 80450 Overseas Highway #204 · $550,000 · 2 bd/2 ba
17. 81801 Overseas Highway ## 729 · $699,000 · 1 bd/1 ba
18. 82779 Old Highway #7 · $4,000,000 · 4 bd/4.5 ba
19. 82779 Old Highway #8 · $4,000,000 · 4 bd/4.5 ba
20. 82779 Old Highway #15 · $3,800,000 · 4 bd/4.5 ba
21. 20 Avacado Street · $15,950,000 · 6 bd/7.5 ba
22. 80450 Overseas Highway #Apt 106 · $550,000 · 2 bd/2.5 ba
23. 82779 Old Highway #14 · $3,950,000 · 4 bd/4.5 ba
24. 81486 Overseas Highway · $22,500,000 · 7 bd/8 ba
25. 81906 Overseas Highway #2 · $2,495,000 · 3 bd/3.5 ba
26. 189 Carroll Street · $1,250,000 · 3 bd/3 ba
27. 191 Carroll Street · $1,250,000 · 3 bd/3 ba
28. 80639 Old Highway #201 · $3,495,000 · 4 bd/4.5 ba · Pending

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