Luxury Homes for Sale in Upper Matecumbe Key Islamorada, FL
The luxury market in Upper Matecumbe Key Islamorada starts at $2,500,000 — about 1.1× the city’s median asking price. This page is every active listing at that level, refreshed nightly from the MLS, with what has actually closed, where the inventory sits and how long it takes to sell. For the wider picture see all homes for sale in Upper Matecumbe Key Islamorada.
12 luxury homes are for sale in Upper Matecumbe Key Islamorada, FL at $2,500,000 and up — median asking $4,249,750, the top listing at $22,500,000. 83% of the luxury inventory is waterfront; 58% is new construction. Median days on market: 200.
Newest luxury listings in Upper Matecumbe Key Islamorada
The most expensive homes for sale in Upper Matecumbe Key Islamorada
| Listing | Asking | Sq ft | $ / sq ft | Community |
|---|---|---|---|---|
| 81486 Overseas Highway | $22,500,000 | — | — | — |
| 20 Avacado Street | $15,950,000 | — | — | — |
| 19 Avacado Street | $13,750,000 | — | — | — |
| 1101 Mastic Street | $6,999,000 | — | — | — |
| 82779 Old Highway #1 | $4,750,000 | — | — | — |
| 150 List Street | $4,499,500 | — | — | — |
| 82779 Old Highway #7 | $4,000,000 | — | — | — |
| 82779 Old Highway #8 | $4,000,000 | — | — | — |
| 18 Pen Key Club | $3,900,000 | — | — | — |
| 82779 Old Highway #15 | $3,800,000 | — | — | — |
Luxury inventory by price
| Band | For sale | Share |
|---|---|---|
| $2,000,000–$3,000,000 | 2 | 17% |
| $3,000,000–$5,000,000 | 6 | 50% |
| $5,000,000+ | 4 | 33% |
How to read this
Luxury is defined here as asking prices at or above $2,500,000. Counts, medians and closings come from active and closed MLS listings as of October 11, 2026; closings are the trailing 12 months. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 25 homes for sale in Upper Matecumbe Key Islamorada.