John Wilson Sells the South Florida Lifestyle by Modeling It
by David Hay
September 2025
It figures that John Wilson wasn’t born in Florida. The fact that the Pittsburgh native moved south a teenager and spent his formative years Fort Lauderdale is not only core to his identity, but it’s also key to his success at selling other non-Floridians on the pleasures of life in the Sunshine State.
Wilson, a Palm Beach-based agent for Douglas Elliman, is especially good at identifying “water people”—the high-net-worth individuals who are ready to embrace the boating life that inspires so many to migrate to the South Florida coast. There’s even a methodology to it.
A resident of Lighthouse Point, where he lives with his wife of 39 years—and fellow Elliman agent—Lisa, Wilson is a regular at the Nauti Dawg, an old-fashioned wooden eatery at the Lighthouse Point Marina. It’s also one of the places where he likes to bring his clients. “I want them to look out over the water, see all the yachts, and take in what’s going down,” he explains.
Often though John and Lisa will then continue this tour in their Suburban. Not everyone is addicted to the ocean. “We show them the ins and out of the Palm Beach area, where the restaurants and stores are, all to give them a base of knowledge to make a decision of where they want to live.”
It’s a successful strategy that helps clients shift from the mindset of a visitor to that of a resident.
“Many of these buyers from the Northeast and elsewhere outside of Florida have already vacationed here,” he tells me. “They think that makes them knowledgeable, but the vacation experience is entirely different from living here. Once we come to talking, they start thinking afresh. And with their imaginations now in full flight—but realistically so—the sale process is a lot easier. They know what they want. I’ve sold them on living here.”
And the clients love it, he adds: “They’ve never had anyone show them real estate in that amount of detail, and they really enjoy it.”
This approach has enabled Wilson to position himself and his business as the go-to contact for wealthy, mostly non-Floridian clients who want to buy luxury property in coastal South Florida. Working with these buyers, he will reach out to fellow agents with listings and offer to work in partnership.
“I always work in tandem,” he tells me. “Not only is it more enjoyable; it’s more productive for all the parties involved, the buyer in particular.”
Forging these all these relationships is key for someone as urbane and savvy as Wilson. “People ask me if I sell real estate. My answer usually is I’m a real estate advisor and being an advisor I build trust with my clients. I can’t tell you how many times I hear from clients which makes my day that they completely trust me. That’s what relationships are all about.”
It helps too that Wilson comes from a real estate family. Their market savvy is not all he’s inherited.
“My father was a smart dresser with a sophisticated fashion sense, and he passed that on to his children,” says Wilson, a one-time model himself who is a devotee of Ralph Lauren and patron of the brand’s store in Palm Beach, which calls him “immediately when a particular jacket or set of shirts goes on sale.”
It’s all of a piece with selling the South Florida lifestyle by effectively embodying it. When he isn’t entertaining at the Nauti Dawg or leaning out the window of his Suburban to greet someone on the street, Wilson, the industry expert, often gives seminars on the Florida market to various business and real estate groups in the Northeast.
While he excels at guiding buyers through the wonders of luxury living by the water, Wilson is also an active agent, with recent sales that include an $11,525,000 apartment in the spectacular Forté on Flagler tower in West Palm Beach, a $6,650,000 home in Boca Raton, a $5.8-million home in Ocean Ridge, and a $2.9-million home close by in Lighthouse Point. He and Lisa currently represent a classic Pompano Beach home just off the Intracoastal Waterway.
The Forté on Flagler sale is a testament to how Wilson has made in-roads in Palm Beach.
“That market is tough,” he says. “During Covid, I first started to make a dent in it. I’m not going to take it over, but the agents there all know I would be excellent to work with, and I have the clients.”
Recalling the pandemic-era frenzy for property everywhere in Florida, Wilson says “the market under $3 million has flattened out.” But he often hearkens back to his father’s wisdom about the market.
“He always maintained that, in the long-term, Florida is recession-proof: over that term—five years and beyond—price points will be higher,” he says. “I think he’s right.”
His impeccable appearance notwithstanding, Wilson doesn’t hesitate to roll up his sleeves during a property inspection or head into a crawl space to assess a faulty AC unit.
“It’s always quicker and more efficient to do it yourself,” he says—part of a compulsion to “know everything,” whether it’s about a listing, the larger market, or all the attractions that keep people moving to Florida. “I know that’s how I’ll get to be best at this.”
David Hay is a well-known architectural writer and playwright. His stories have been featured in The New York Times, Dwell and New York.
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