Browse the latest homes for sale in Islamorada, FL — from oceanfront estates and bayfront retreats to canalfront homes and waterfront condos. Listings are pulled directly from the Florida Keys MLS and updated daily, so you’re always seeing what’s actually available in the market.
Islamorada is the heart of the Upper Florida Keys — a string of six islands spanning from Plantation Key to Long Key, known as the Village of Islands. It’s one of the most sought-after addresses in the Keys for a reason: the fishing is world-class, the water is impossibly clear, and the pace of life is one most people only dream about.
Properties here range from modest canal-front cottages to multi-million dollar oceanfront estates with private dockage. Whether you’re drawn by the boating, the diving, the sunsets over Florida Bay, or simply the idea of waking up on the water every day, Islamorada delivers.
Waterfront is the name of the game in Islamorada. Most buyers are looking for direct water access — whether that’s ocean frontage, bay views, or a private boat slip on a deep-water canal. The market spans a wide range, but waterfront properties move quickly and competition is real, especially for well-positioned homes with dockage and strong rental history.
Our team is based in Islamorada and works this market every day. We know the neighborhoods, the buildings, and the nuances that don’t show up in a listing — which communities allow vacation rentals, which canals have the best ocean access, and where the value is right now.
Use the search below to explore current listings, or contact Shane to talk through what you’re looking for. Whether you’re buying your first Keys property or adding to a portfolio, local knowledge makes all the difference.
© 2026 Shane "Waterfront" Wilson Team.
85960 Overseas Hwy Suite 4