Islamorada, known as the Village of Islands, encompasses Plantation Key, Windley Key, Upper Matecumbe Key, and Lower Matecumbe Key. Waterfront inventory here is limited and values run higher than most of the Keys. This page shows canalfront, bayfront, and oceanfront homes priced under $1.5 million, updated in real time from the MLS.
Islamorada draws serious boaters and anglers for good reason. Oceanfront properties sit on the Atlantic side with direct access to world-class offshore fishing. Canalfront homes offer protected dockage with quick runs to both the ocean and Florida Bay. Bayfront properties face the backcountry flats on Florida Bay, the waters that define Islamorada's reputation as the Sport Fishing Capital of the World.
Use the search tools above to filter by price, water type, or size. For a personalized search or questions about a specific listing, contact Jim Signor at 305-394-4449.
A waterfront home in Islamorada has direct water frontage, including canalfront lots with dockage, bayfront properties on Florida Bay, and oceanfront homes facing the Atlantic.
Yes, though options are limited. Islamorada waterfront values run higher than most of the Keys, but properties still appear in this range.
Canalfront homes offer protected dockage with quick access to both the ocean and Florida Bay. Bayfront properties face the backcountry flats on Florida Bay. Oceanfront homes face the Atlantic and direct access to offshore fishing.
Listings are pulled directly from the Florida Keys MLS and updated every five minutes.
Welcome to stunning Florida Bay views and breathtaking sunsets in the heart of Plantation Key! This beautifully remodeled and fully furnished modular home offers the perf...
Experience the ultimate Keys lifestyle in this beautifully furnished and impeccably maintained waterfront pool home in desirable Lower Matecumbe Key. Offering 60 feet of ...
Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buyers spend years searching for, this one-of-a-kind oceanfront retreat delivers the...
Everything you need and nothing you don't. This ground-level 3-bedroom, 3-bathroom home offers an easy, functional layout with that unmistakable Florida Keys feel the mom...
Charming 2-bedroom, 2-bath ground-level canal-front home located in a highly desirable Florida Keys neighborhood. The home features a split floor plan with a one-bedro...
Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept floor plan with 2 bedrooms and 2 bathrooms. Tastefully furnished with a coastal...
ACTIVE BUILDING AND DOCK PERMITS. BUILD RIGHT AWAY. Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. ...
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, ...

Jim Signor: 305-394-4449