Paradise From All Perspectives – Shane Wilson

The steady hum of the small aircraft engine fills the cabin as Shane Wilson banks gently to the left, revealing the stunning island chain below. From this altitude, the Keys transform into a mosaic of emerald and turquoise, connected by the silver thread of the Overseas Highway.

“You haven’t truly seen the Keys until you’ve experienced them from every angle—by sea, by land, and especially by air,” Shane says, his aviator sunglasses reflecting the pristine waters that have shaped his life since childhood.

For this third-generation Conch, flying between his real estate offices in Islamorada and Fort Myers isn’t just practical—it’s a perfect metaphor for how he approaches both life and business, finding joy and opportunity from multiple perspectives.

“Eight years ago, I got my pilot’s license and a plane,” he explains, eyes lighting up with the same enthusiasm he had as a kid exploring these waters by boat. “Now I can fly between locations in just 55 minutes, have an open house in Fort Myers in the morning, show a house in the Keys in the afternoon, and still have time for snorkeling before sunset.”

As he guides the plane toward Tavernier Airport, Shane points out landmarks below—canals where he knows the perfect waterfront properties, reefs where he takes clients fishing, and marinas where he once tied up his 13-foot Whaler as a kid.

“This was our playground,” he reminisces. “After school, my buddies and I would load up my 13-foot Whaler and head out to catch lobster, stone crab, grouper, or mahi.”

Those youthful expeditions were more than just fun; they were Shane’s first entrepreneurial ventures.

“We’d contact our parents and their friends beforehand—’What do you guys want?’—then go catch it and sell it to them. That money would keep snacks in our bellies and gas in the boat.”

A Legacy Rooted in Real Estate

This early entrepreneurial spirit reflected the influence of his family’s deep roots in Keys real estate. For over 65 years, the Wilson/Murray family has shaped the landscape of the islands, with Shane’s grandparents and parents building, buying, and selling iconic properties, including the Tamarind Bay Club.

“Real estate is literally in my blood,” Shane says. “My grandparents, Lyle and Dee Murray, my uncle, Tim Murray, and my parents—they were all in the business. My father, Bill Wilson, worked as both a general contractor and realtor, and my mother, Mimi Murray Wilson, worked alongside him to build their reputation as respected brokers.”

After graduating from Coral Shores in 1986, Shane followed the family tradition by getting his real estate license. As his family was winding down their careers and entering retirement, Shane was entering the profession.

This timing led him to continue the family legacy, building his stellar reputation for over 30 years as Shane “Waterfront” Wilson in Southwest Florida. With a strong client base in the Keys and the Fort Myers area, Shane has offices in both regions.

Solving Problems with Altitude

The traffic-laden drive between locations, however, was cutting into Shane’s philosophy of making every day count. So, true to form, Shane didn’t just identify a problem—he crafted a solution that enhanced his lifestyle and business simultaneously. Within no time, he was flying instead of driving, saving time while improving the view.

This aerial perspective gives Shane a unique advantage when showing properties.

“Sometimes clients in Southwest Florida are interested in the Keys but don’t have time for the long drive for a showing. They hop in the plane with me, and not only do they save time, but they get that breathtaking birds-eye view of the islands. It gives them a whole new appreciation for what makes this place special.”

Life on the Water

When he’s not showcasing the Keys from above, Shane is showcasing properties from the water.

“I specialize in waterfront properties, so I’ll frequently take clients out on the boat to show them homes. But it’s more than just the houses—I’m showing them the lifestyle.”

These excursions might include a trip to Alligator Lighthouse, a stop at a waterfront restaurant, or even catching fish for the restaurant to cook up.

“That’s what people are really buying here—not just a house, but a way of life. The boating, fishing, snorkeling, diving—I’ve done it my whole life, so I can be their guide to finding the perfect match for their dreams.”

Expert Guidance with a Personal Touch

Shane’s intimate knowledge of the waterways provides practical value too.

“If a client already has a boat, I know exactly which canals and neighborhoods will work best for them. If they’re looking for something more affordable with easy water access, I can point them to neighborhoods with boat parks that only residents can use.”

This personal touch and local expertise have not gone unnoticed. Shane has helped over 1,000 satisfied clients and earned numerous professional designations: ABR, RMM, GRI, CRS, and membership in The Institute for Luxury Home Marketing, among others.

Shane doesn’t provide this premier service all on his own. Rachel steps in wherever is needed and Shane’s wife, Anne, brings over 18 years of experience as a broker.

“Anne is a perfect partner in life and business,” he says warmly. “I’m the front guy, but Anne handles everything behind the scenes. I couldn’t do what I do without her keeping everything running smoothly.”

Giving Back to the Community

Beyond his business success, Shane remains deeply connected to the community that shaped him. The Shane “Waterfront” Wilson Team regularly sponsors and participates in local events like the Conch Scramble and Nick Sheahan’s Dolphin Rodeo.

“Sometimes I’ll bring customers down to experience these events—they’re so much fun and show what our community is all about.”

Their community involvement extends to supporting local youth athletics, with banners at the Founders Park Baseball Field and Coral Shores’ football field.

A Life Well Lived in the Keys

As the sun begins to set over the bay, painting the water in shades of orange and gold, Shane reflects on the philosophy that has guided his life and career:

“There’s more to life than just working. Being able to walk out to your boat and take it out for the day or the evening—that’s what it’s all about. I’m so lucky that I get to show people a unique perspective on that amazing Keys lifestyle.”

With a view of the Keys from every angle—by boat, by plane, and through the eyes of a true Conch—Shane “Waterfront” Wilson continues to help others find their own piece of paradise, making every day a great day in the process.

To experience the Keys lifestyle from every angle, visit ShaneWaterfrontWilsonTeam.com

Written by Jerrica Mah — writer, Army wife, and freelance book editor who loves to travel vicariously through stories.