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What to Know Before Buying a Waterfront Property in the Florida Keys

By September 30, 2025No Comments

A local’s guide to what really matters—beyond the view

There’s nothing quite like waking up to the sound of the tide rolling in, or watching the sunset light dance across the bay from your own dock. But if you’re thinking about buying a waterfront property in the Florida Keys, there’s more to consider than just the view.

I’ve been around these waters my whole life—from navigating tight canals as a kid to helping buyers find the right homes with boat access, dockage, and lifestyle compatibility. If you’re dreaming of the Keys life, here’s what you need to know before you dive in.

Not All Waterfront is Created Equal

Sure, “waterfront” sounds like a dream—but in the Keys, it comes in all forms:

  • Oceanfront: Open Atlantic views, direct ocean access, and typically higher price points.

  • Bayfront: Often more protected waters and stunning sunset views, with quick access to backcountry fishing.

  • Canalfront: Usually the most common and affordable option, but canal depth, width, and access to open water vary dramatically by neighborhood.

Shane’s Tip: Some canals are better suited for flats boats or center consoles, while others can comfortably handle a 60’ sportfish. Always ask about draft, clearance, and tidal flow before falling in love with the lot.

Bridge Clearance + Navigational Access

There’s one drawbridge in Islamorada—Snake Creek—which gives boaters in neighborhoods like Venetian Shores direct access between Florida Bay and the Atlantic. Some areas have no fixed bridges, while others may limit boat size due to low-clearance bridges or narrow canals.

Knowing how and where you plan to boat is crucial:

  • Offshore angler? Look for direct ocean access and deeper canals.

  • Flats fisherman or paddleboarder? A shallow canal with mangrove protection may suit you perfectly.

  • Weekend cruiser? Consider communities with marinas or boat lifts for convenience.

Home Condition + Insurance Considerations

Waterfront homes in the Keys are built to endure the elements—but age, elevation, and construction type all impact insurance rates, maintenance needs, and long-term value.

  • Newer homes or elevated structures often qualify for better wind mitigation discounts.

  • CBS (concrete block) homes with metal roofs are ideal.

  • Older ground-level homes may be charming but can come with higher flood premiums.

I always recommend getting a wind mitigation + 4-point inspection early—even before making an offer—so there are no surprises.

Dockage: Deeded, Shared, or None at All?

In the Keys, dockage is gold—and not every waterfront home has it.

  • Deeded dockage gives you private access, sometimes with lifts or boat slips.

  • Shared or community dockage may have limited space, rules, or fees.

  • No dockage? You’ll need to budget for a nearby marina slip (if you can find one).

Some properties also have submerged land rights, allowing for future dock installation—others do not. That’s where a local agent (👋) can help you navigate the legal and permitting side.

Lifestyle, Location & Local Vibe

Do you want to walk to your favorite seafood shack after a day on the water? Be close to top schools or work remotely with a strong Wi-Fi connection? Different parts of the Keys offer very different lifestyles:

  • Key Largo: Closest to the mainland, great for commuters, retail access, and popular waterfront neighborhoods like Port Largo and Anglers Park.

  • Islamorada: Sportfishing capital, luxury homes, and vibrant communities like Venetian Shores, Plantation Key, and Upper Matecumbe.

  • Marathon + Lower Keys: More quiet, open space, and often better value per square foot.

  • Key West: Historic charm, higher density, and limited dockage—be ready for a unique waterfront experience.

Work with Someone Who Knows the Water (and the Rules)

I’ve helped hundreds of buyers and sellers over the years, but what sets me apart is this: I know these waters like the back of my hand—because I’ve been boating, fishing, diving, and working here my whole life.

When I tour waterfront homes with clients, I often take them out by boat too. Because you don’t just buy the house—you buy the lifestyle, the canal, and the access that comes with it.

Ready to Find the Right Keys Waterfront Property?

Whether you’re looking for an oceanfront estate, a canalfront Keys classic, or a bayside retreat with space for your boat and family, I’ll help you navigate the real estate side—and the water side.

Reach out to start your search, and let’s go take a look—by land or by sea.

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