Islamorada Homes for Sale
Four islands, one village, and the best sportfishing on earth — searched with the broker who lives here.
Islamorada real estate carries a reputation the rest of the chain doesn't quite match. The Village of Islands — Plantation Key, Windley Key, Upper Matecumbe, and Lower Matecumbe — is the sportfishing capital of the world, the dining capital of the Keys, and the address serious Keys buyers ask for by name. It's also home: Palm House Real Estate operates from Islamorada, and AJ Vetter has fished, boated, and sold these four islands his whole life.
Islamorada homes for sale run the full spectrum, from bayside condos to the open-water estates that anchor the Upper Keys luxury market. What they share is scarcity — village growth limits and ROGO permitting keep new inventory tight, which is a large part of why Islamorada holds value the way it does.
Islamorada neighborhoods
Venetian Shores
The marquee canal neighborhood of the Upper Keys, on Plantation Key's ocean side: wide, deep canals cut for real boats, flow-through water, and quick access through Snake Creek — one of the few drawbridge passes in the Keys, which means sailboat-friendly clearance. Venetian Shores commands a premium and earns it.
Port Antigua
On Lower Matecumbe's bayside, Port Antigua pairs a private homeowners' beach with canal dockage and backcountry access. It's the neighborhood out-of-town buyers fall for on the first visit — sand, sunset, and a boat behind the house.
Lower Matecumbe
The village's quiet southern island: larger lots, open-water frontage on both sides, and some of the most significant estates in the Upper Keys. White Marlin Beach and the Port Antigua/Safety Harbor stretch carry most of the inventory. Lower Matecumbe is where the $2M+ conversation usually starts — see Waterfront & Luxury.
Plantation Key (village side)
The village's northern island mixes established canal neighborhoods, the Founders Park corridor, and school-and-services convenience. The Tavernier–Islamorada line crosses Plantation Key, so confirm which jurisdiction a listing sits in — rental rules differ.
Windley Key
Small, central, and busy — home to Holiday Isle's resort energy and a handful of residential pockets. Condo and townhome product here suits buyers who want walk-to-everything Islamorada.
Water & dockage in Islamorada
The village offers every water type the Keys have: oceanside canals with reef access, bayside basins with flats-boat draw, and open-water frontage on both sides. Two local details matter more than most listings admit. First, Snake Creek's drawbridge makes northern Plantation Key uniquely friendly to sailboats and larger sportfish. Second, bayside depth varies street by street — a flats skiff and a 40-foot sportfish do not shop the same canals. Deep-water dockage on the ocean side is the scarcest, most defended asset in the village.
Islamorada waterfront homes for sale and the village's condo inventory each carry their own dynamics — waterfront trades on dockage specifics, condos on the handful of bayside communities with marinas.
Market snapshot
Islamorada is the Upper Keys' premium market. Entry points are condos and dry-lot homes from the high six figures; canal-front homes generally run $1.5M–$3M with dockage quality driving the spread; open-water estates on the Matecumbes trade from $3M well into eight figures. Inventory is chronically thin — the buyers who win here are the ones with alerts set and financing ready.
Islamorada questions buyers ask
What are Islamorada’s vacation-rental rules?
The village regulates short-term rentals tightly — in most residential districts, rentals under 28 days require a village vacation-rental license, and licenses are limited. If rental income matters to you, make the license status of any property a day-one question.
What is ROGO and why does it matter?
The Rate of Growth Ordinance caps new building permits across the Keys to manage hurricane evacuation times. Practically: buildable lots carry real scarcity value, and permitted, existing structures are worth defending. It's a major reason Islamorada supply stays tight.
Which neighborhood has the best boating access?
Depends on the boat. Venetian Shores for big hulls and sailboat clearance through Snake Creek; Port Antigua for backcountry skiffs; Lower Matecumbe oceanside for direct deep-water runs. This is exactly the conversation to have with AJ before touring.
Is Islamorada right for full-time living?
The village supports it better than most of the chain — schools, Founders Park, medical services in neighboring Tavernier, and a year-round community alongside the seasonal one.
How competitive is the market?
The good properties move on relationships and readiness. A saved search plus a broker who hears about listings before they post is the honest playbook here — it's AJ's backyard.
This is our home water.
Get Islamorada listings the hour they post — or call the broker who grew up here.
Save a Search Get the Buyer's Guide Talk to AJ