Waterfront Homes for Sale in Upper Matecumbe Key Islamorada, FL
This page tracks every Upper Matecumbe Key Islamorada listing whose MLS record reports waterfront (ocean, bay, Intracoastal, river, canal or lake frontage), by community, with live counts and asking prices, and the costs that come with the water.
21 waterfront homes are for sale or pending in Upper Matecumbe Key Islamorada, FL today across 10 communities. The median asking price is $4,000,000, from $595,000 to $29,500,000. Most listings right now: Strattons (82.5) (6), Russell Estates (83.2) (5), Misc Upper Matacumbe (82.0) (3). Updated September 8, 2026 from the MLS.
Upper Matecumbe Key Islamorada waterfront homes by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Waterfront Homes | New build | Median list | From |
|---|---|---|---|---|
| Strattons (82.5) | 6 | 1 | $1,605,000 | $649,000 |
| Russell Estates (83.2) | 5 | 5 | $4,000,000 | $3,800,000 |
| Misc Upper Matacumbe (82.0) | 3 | 2 | $15,950,000 | $13,750,000 |
| Tea Table (79.5) | 1 | 0 | $29,500,000 | $29,500,000 |
| Caribee Beach (80.0) | 1 | 0 | $7,400,000 | $7,400,000 |
| Venetian Shores (86.0) | 1 | 1 | $4,500,000 | $4,500,000 |
| Maison Matecumbe (81.0) | 1 | 0 | $3,495,000 | $3,495,000 |
| Misc Condo Upper Mat (82.0) | 1 | 1 | $3,195,000 | $3,195,000 |
| Bay Colony Villas (81.5) | 1 | 0 | $2,485,000 | $2,485,000 |
| Sand Pebbles (80.5) | 1 | 0 | $595,000 | $595,000 |
What waterfront ownership really costs
Waterfront homes carry costs inland homes do not: flood insurance where the parcel sits in a FEMA special flood hazard area, higher windstorm premiums closer to open water, and upkeep for seawalls, docks and lifts. Before you offer, pull the FEMA flood zone for the specific parcel, ask for the seawall’s age and any inspection reports, and get an insurance quote in hand, not an estimate. Our flood insurance calculator and wind mitigation savings calculator show what the parcel will actually cost to insure.
Questions to ask about any waterfront listing
Is the water frontage deeded or association-owned? Is there a fixed bridge between the dock and open water, and what is the clearance? What did the seller pay for flood and wind coverage last year, and with which carriers? Has the seawall or dock been permitted and inspected? What is the finished-floor elevation? A local agent who works waterfront deals will know which canals hold depth at low tide and which carriers are writing in the area.
Common questions
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Live data: floridakeys, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Upper Matecumbe Key Islamorada, FL whose MLS record reports waterfront. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.