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The Podcast

Loving the Florida Lifestyle

Shane Waterfront Wilson and host Charly Caldwell II on Florida waterfront living: the Keys, Southwest Florida, boating, and buying and selling homes on the water. Every episode includes a full transcript.

Episode 5 · April 4, 2026 · 1:53:25

Florida Keys Waterfront Homes Guide: Key Largo to Key West

Recorded at Shane's home in Islamorada, this episode works down US 1 from Key Largo to Key West: which neighborhoods suit big boats, bay or ocean access through the creeks and cuts, canal widths and depths, and what seasonal rentals bring in.

  • Keys neighborhoods by mile marker
  • Venetian Shores
  • Bay vs. ocean access
  • Canal width, depth and dock rules
  • Seasonal rentals
Watch & read the transcript → · YouTube

Episode 4 · October 13, 2025 · 1:28:44

Southwest Florida Waterfront Neighborhoods: Gulf Harbour, McGregor Isles, Cape Harbour & More

A community-by-community tour of waterfront Fort Myers and Southwest Florida: McGregor Isles, Town and River, Palmetto Point, Gulf Harbour, Iona and more, plus seawalls, flood zones and insurance, and when Cape Coral is the better value.

  • Fort Myers waterfront neighborhoods
  • Gulf Harbour marina and slips
  • Seawalls and flood zones
  • Insurance
  • Cape Coral vs. Fort Myers
Watch & read the transcript → · YouTube

Episode 2 · July 10, 2025 · 2:07:13

Pricing Your Florida Waterfront Home in Today's Market

Fresh off a listing appointment, Shane walks through how to price a waterfront home when the market softens, what sellers ask him, and why knowing each community's water matters, including the shallow canal mouths that can trap a big boat in otherwise deep neighborhoods.

  • Pricing in a downturn
  • Listing appointment questions
  • Shane's service area
  • Canal-mouth depth traps
Watch & read the transcript → · YouTube

Episode 1 · April 16, 2025 · 1:49:34

Meet Shane Waterfront Wilson: 30+ Years Selling Florida Waterfront Homes

Shane tells the story of growing up on the water in Key Largo in a family of Realtors, builders and developers, and how 33 years of selling waterfront homes in Fort Myers and the Florida Keys grew out of it. He explains his "what's your application?" method for matching people to the right boat, water and neighborhood.

  • Shane's background
  • Referral-based business
  • Choosing a boat for how you'll use it
  • Cape Coral canals and bridges
  • Keys boat parks and creeks
  • Flying between the Fort Myers and Keys offices
Watch & read the transcript → · YouTube