(239) 851-3861 call or text
Search Southwest Florida Homes Search Florida Keys Homes
Shane Waterfront Wilson Team Real Estate

Florida Keys

Islamorada Waterfront Homes

The Village of Islands in the Upper Keys, where Shane Waterfront Wilson went to high school, keeps his boat and lives on the water.

Search Islamorada Listings Get the Free Guides

About Islamorada

Islamorada is a village of islands in the Upper Florida Keys that includes Plantation Key, Windley Key and Upper and Lower Matecumbe. It's home to some of the Keys' best-known waterfront neighborhoods and has easy access to both Florida Bay and the Atlantic.

Shane Waterfront Wilson was raised in the Keys and graduated from Coral Shores High School in 1986. Today he lives in Treasure Harbor, oceanside at mile marker 86.5.

In Islamorada, the first question is bay side or ocean side. Bay-side homes give you sunsets and the backcountry. Ocean-side homes give you sunrises and a quick run to the reef. Wherever you live, Tavernier Creek, Snake Creek and Whale Harbor connect the two sides, so you're rarely more than a few minutes from either.

The other big question is your boat. Canal widths and depths vary a lot from one neighborhood to the next, and some deep canals have a shallow mouth that a big boat can't clear at low tide. Shane knows these waters by boat and will show you the run from any home before you buy.

Updated November 9, 2026 by Shane Waterfront Wilson

Neighborhoods

Waterfront Communities in Islamorada

Treasure Harbor

Oceanside, mile marker 86.5

Shane's Keys neighborhood. Deep at the docks, but the harbor entrance runs shallow, so bigger boats time the tide.

Guide coming soon

Plantation Key Colony

Plantation Key

Quick access to Tavernier Creek and Snake Creek. Some canals are only 40 to 50 feet wide, which limits dock build-out.

Guide coming soon

Port Antigua

Lower Matecumbe

Deep water and its own private beach, White Marlin Beach.

Guide coming soon

Getting Around by Boat

Bay Side, Ocean Side, and the Creeks Between

Tavernier Creek

The bridge over Tavernier Creek is low. Shane has had to fold down a canopy and have the crew hold the outriggers down to get under it, so check your boat's height.

Snake Creek

Snake Creek has a drawbridge with 27 feet of clearance when closed. Taller boats wait for it to open.

Watch the canal mouth

A canal can be 13 feet deep at the dock and 5 feet at the entrance. Shane used to anchor his Cabo outside Treasure Harbor and wait for high tide to bring it in.

Dock build-out

Docks can extend about 25% of a canal's width. On a narrow canal, that may not be enough for a wide-beam boat.

Sources: Snake Creek Bridge (Waterway Guide)

Free Guides & Checklists

Buying or Selling on the Water?

For Buyers

Florida Waterfront Home Buyer's Guide & Checklist

What to check before you make an offer on a Florida waterfront home.

  • Match the home to your boat: length, beam, draft and bridge clearance
  • Water depth at the dock, in the canal and at the canal mouth at low tide
  • Seawall, dock and lift inspection checklist
  • Flood zone, elevation and insurance questions to ask early

For Sellers

Florida Waterfront Home Seller's Guide & Checklist

How to prepare, price and present your waterfront home.

  • Pricing for the market you're actually in, not last year's
  • Pre-listing checks for seawalls, docks, lifts and termites
  • Documents waterfront buyers will ask for
  • Showing your home from the water side

Browse all of Shane's guides →

Client & Neighbor Stories

What People Say

“I wouldn't change a thing. I'm so happy we came here. I'm so happy that we took that chance, because we weren't sure. It's almost like we're in a cool little bubble here that not everybody knows about.”
Rachel Foreman Islamorada resident, Treasure Harbor. Bought the home across the street from Shane's. From podcast episode 6

Read more testimonials →

Videos, Photos & Podcast

See and Hear Islamorada

Shane on Islamorada, from the podcast

All podcast episodes →

Islamorada FAQ

What islands make up Islamorada?

The Village of Islamorada includes Plantation Key, Windley Key, and Upper and Lower Matecumbe Keys in the Upper Florida Keys.

How do boats get between Florida Bay and the Atlantic in Islamorada?

Through the cuts under US 1, including Tavernier Creek, Snake Creek and Whale Harbor. Check bridge heights and tides for your boat.

Should I buy bay side or ocean side in Islamorada?

It depends on how you'll use the water. Bay side offers sunsets and backcountry fishing. Ocean side offers sunrises and a quick run to the reef. Many neighborhoods are minutes from a creek, so you can reach both.

Let's Find Your Place in Islamorada

“Islamorada is home. I went to high school here, I keep my boat here, and I've fished every one of these creeks. Tell me how you want to live on the water and I'll show you the neighborhoods that fit, by boat.”
— Shane

Call or Text Shane Email Shane Search Islamorada Listings

(239) 851-3861 (call or text) · shane@shanewaterfrontwilson.com
Florida Keys Office: 85960 Overseas Hwy, Islamorada, FL 33036

Nearby