When I first started boating in the Florida Keys as a kid, I had no idea it would lead me here—decades later—helping clients navigate not just our waterways, but the unique decisions that come with buying waterfront property in Southwest Florida.
If you’re considering a waterfront home here, you’re not alone. Whether it’s the canal-lined streets of Cape Coral, the bayfront beauty of Bonita Springs, or the Gulf-facing estates in Naples, waterfront real estate in Southwest Florida continues to draw buyers from around the world. And with good reason: it’s hard to beat sunrise coffee on your lanai, boat keys on the hook, and the water just steps from your back door.
But owning a waterfront home is a little different than your average real estate deal—there are tides to consider, seawalls to inspect, and zoning laws that change by zip code. That’s where a little local knowledge goes a long way.
Let’s dive in.
Waterfront condos in Fort Myers, Florida
Understanding Waterfront Living in Southwest Florida
Not all waterfronts are created equal. In fact, one of the first questions I ask clients is: “What do you want out of the water?”
Do you want deep-water access for your sportfishing boat? Or are you dreaming of kayak mornings and paddleboard evenings? That answer helps narrow down your options.
Canal vs. Bay vs. Gulf-Front
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Canalfront Homes (especially in Cape Coral or Fort Myers): Ideal for boaters. Some canals offer direct, sailboat-access with no bridges to the Gulf. Others require longer idle times or have fixed bridge heights.
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Bayfront Homes (Bonita Springs, Estero, Naples Bay): Scenic and peaceful. You get incredible wildlife views and great access to the Intracoastal. These homes often fetch a premium for their vistas.
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Gulf-Front Homes (Naples, Fort Myers Beach): The dream. Steps from sand and surf, these homes are rare, often luxurious, and come with higher maintenance and insurance needs.
Maintenance & Insurance Considerations
Waterfront ownership means staying ahead of a few things:
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Seawall or dock upkeep (older homes may need repairs)
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Hurricane impact windows / elevated construction (important for flood zones)
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Flood insurance – Yes, it’s required for most homes near water, and costs can vary widely based on elevation and FEMA zone.
When I work with clients, we look into past flood claims and elevation certificates upfront—so you know exactly what you’re getting into.
Key Areas to Explore in Southwest Florida
I’ve spent years boating and selling homes across this entire coastline. Here are some of my top picks, with a few notes from my own experience.
Cape Coral
Often the first stop for buyers exploring Southwest Florida waterfront real estate, Cape Coral offers more canals than Venice, Italy. Seriously—over 400 miles of them. Homes range from affordable entry points to custom estates on intersecting canals with sailboat access.
Explore Cape Coral Waterfront Homes for Sale
Naples
Gulf-front estates, historic Old Naples charm, and newer developments on Naples Bay. If luxury and lifestyle are top of your list, this town delivers. Waterfront homes here are an investment in both real estate and quality of life.
Explore Naples Waterfront Real Estate
Estero & Bonita Springs
Quiet, scenic, and still somewhat under-the-radar, these towns offer access to Estero Bay and the Imperial River. If you’re a nature-lover or looking for privacy with great boating options, this area is worth exploring.
Browse Bonita Springs Waterfront Homes for Sale
Fort Myers Beach & McGregor Isles
The heart of boating culture. Fort Myers Beach is rebuilding with modern coastal homes and investment potential. McGregor Isles, where I live, offers a quick idle out to the river—and a tight-knit, water-loving community.
Explore McGregor Isles Waterfront Homes
Tips for First-Time Waterfront Buyers
Here’s what I tell every buyer (after they ask how long it takes to get to the Gulf):
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Know your dockage – Does the home have a lift? Are there restrictions? Can your boat clear the bridges?
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Check the seawall – Older concrete seawalls or wood pilings may need repairs or replacement.
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Ask about flood history – Just because it’s been dry doesn’t mean it always will be.
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Financing? – Waterfront homes can require higher insurance and more detailed appraisals. Get pre-approved with a local lender who understands coastal lending.
Current Market Trends in SWFL Waterfront Real Estate
Inventory has shifted. We’re seeing more listings than we did a year ago, especially in Cape Coral and Fort Myers Beach. That said, well-priced homes with strong waterfront access are still moving quickly.
Median price points (as of this writing):
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Cape Coral waterfront home: ~$599,000
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Fort Myers Beach condo: ~$649,000
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Naples Gulf-front estate: $5M+
And yes, new construction is trending—especially in areas rebuilding after the storms. If you’re thinking about building new, I’ve worked with several great local builders and can help you vet lots, seawall condition, and zoning requirements.
Shane “Waterfront” Wilson’s boat
Why Work with a Waterfront Specialist?
There’s a difference between showing homes and showing homes by boat.
I’ve been boating these waters for over 40 years—from my early days in the Keys to guiding clients now from Sanibel to Naples. I know how long it’ll take you to get from a canal to the cut. I know which streets have deep water and which ones get a little skinny on a negative tide. And I’ll tell you that upfront.
I help buyers see what it’s like to live on the water—not just own a house next to it.
Let’s Go Find Your Spot on the Water
If you’re thinking about buying a waterfront home in Southwest Florida, you’re not just buying real estate—you’re buying a lifestyle. Whether you picture yourself casting a line at sunset, grabbing lunch by boat, or just sipping coffee while manatees swim by, I’d love to help you get there.
Feel free to reach out if you want to talk options—or better yet, hop on the boat for a tour.
