Florida Keys Homes for Sale — Search Every Island from Key Largo to Key West
110 miles of islands. One search. Every listing in the Florida Keys, updated from the MLS and guided by a Keys native.
Fly the chain ↓ · MM 106 → MM 0
Key Largo — The first island. The diving capital.
An hour from Miami and a world away, Key Largo is where the chain begins. It's the largest island in the Keys and the easiest commute back to the mainland — which is why so many first-time Keys buyers start here. Canal-front neighborhoods like Port Largo put a dock behind the house and John Pennekamp's reefs out front. Homes range from ground-level conch cottages to bayfront estates with open-water sunsets.
MM 106 — where the Overseas Highway begins
Tavernier — The historic quiet between the headlines.
Tavernier is the Keys most visitors drive past — and the one longtime locals quietly prefer. One of the oldest settlements in the island chain, it keeps its history in its wooden Red Cross houses and its pace a notch slower than Key Largo next door. Buyers come here for value: canal-front homes and Plantation Key addresses that cost noticeably less than the same water a few mile markers south.
Est. 1860s — among the oldest settlements in the Keys
Islamorada — The Village of Islands. Our home base.
Islamorada is four islands wearing one name — Plantation Key, Windley Key, and the two Matecumbes — and it's the sportfishing capital of the world. It's also home: Palm House Real Estate is based here, and AJ Vetter has spent his life on these flats. From Venetian Shores' wide canals to Lower Matecumbe's open-water estates, this is the Keys' sweet spot of boating, dining, and serious real estate.
4 islands, 1 village — sportfishing capital of the world
Marathon — The heart of the chain, built for boaters.
Marathon sits mid-chain with the Seven Mile Bridge at its foot and water on every side. It's the most boat-centric town in the Keys — Boot Key Harbor, dozens of canal neighborhoods, and quick runs to both the Atlantic and the Gulf. Duck Key adds resort-style waterfront living, and Key Colony Beach is its own tidy beach city next door. If dockage tops your list, start your search here.
Mid-chain — Atlantic and Gulf access from one dock
Key West — Mile Marker 0. The end of the road.
Key West is the island everyone knows and the market everyone watches. Old Town's conch houses and the Casa Marina district's estates hold their value like little else in Florida, and demand runs year-round. It's a walking town with an airport, a harbor, and 200 years of architecture — the most searched real estate market in the Keys by a wide margin. The road ends here; for many buyers, the search does too.
MM 0 — the southernmost city in the continental U.S.
Open water, bayfront, or canal front?
In the Keys, the water behind the house matters more than the house. Open-water estates trade sunsets and views for exposure; canal-front homes trade views for protected dockage; bayside means calmer water and evening light. If you're searching above the $2M line — or just want the dockage answered before you fall for a listing — start with our waterfront guide.
Explore Waterfront & Luxury Homes
Search with a Keys native, not a search engine
AJ Vetter grew up on these islands and has spent 15+ years selling them — he's a top-1% agent in the Upper Keys and the broker behind Palm House Real Estate in Islamorada. Out-of-town buyers work with AJ because he answers the questions listings can't: which canals get skinny at low tide, what flood insurance really runs, and which streets rent legally.
Meet AJ“AJ Vetter is the best realtor/broker we have ever known. He and his team were able to quickly sell our home, holding our hands every step of the way. His team goes above and beyond the standard. We would recommend him to anyone in the keys.”
Ana Walter Google review“AJ, was very professional, experienced and easy to work with. Excellent service with my transactions.”
John Walsh Google review“Professional and business savvy! I will use them again.”
Thomas Nagy Google reviewBuying from out of state? Read this first.
The free Out-of-State Buyer's Guide covers what Keys listings never mention: flood and windstorm insurance, ROGO permits, vacation-rental rules by city, and how to buy remotely without a wasted trip.
Get the Free Guide