The self-proclaimed “Prince of Montauk” is still riding high.
Last year, after he was the subject of a profile in Vanity Fair — in which he was described as a “real estate agent to the stars,” “unofficial bouncer of the local surf beaches” and, most improbably, “the inspiration for Cole Lockhart, Joshua Jackson’s character on ‘The Affair’” — Mr. Eckardt was arrested by the East Hampton police on charges of driving while under the influence of drugs.
Some longtime Montauk residents were ready to write him off as a washed-up party boy, but he has defied expectations.
This year he has sold more than $15.5 million in homes and commercial properties, according to Nest Seekers, the firm for which he works. He is the broker for one of the town’s largest commercial listings: Zum Schneider, a 4,040-square-foot German-style restaurant and beer garden that is on the market for $4.1 million.
Recently, he got the exclusive on a four-bedroom home with water views owned by the surfer and artist Tony Caramanico, priced at $3.2 million. And Mr. Eckardt is in the process of closing a $27 million deal that he said he couldn’t talk about because of a nondisclosure agreement.
“I believe I’m the realest real estate agent out here,” he said. “Whatever I touch turns to sold.”
“I know what this town needs,” he said. “I visualize greatness.”
Raised by a fisherman and waitress in Montauk, Mr. Eckardt always dreamed of being a surfer and traveling the world. He moved to California in his late teens to attend Santa Barbara City College before moving to Malibu to surf. When he saw how quickly Malibu was developing, he also found a passion for real estate.
“If I continued to grind, who knows what would have happened,” he said. “But I saw myself doing more than that.”
So, five years ago, Mr. Eckardt returned to Montauk, just as his hometown was undergoing a real estate transformation, from quiet fishing village to high-roller beach resort.
His surfer connections and native-son status, he thought, would mesh perfectly with Montauk’s new scene.
“Everywhere that I have traveled to surf, I’ve also built a résumé,” he said. “Even now I’m working on a project in Montauk with some people from Central America that knew me from surfing when I was younger.”
“I literally use the beach as my office,” he added.
Before he heads to his favorite spot, the Ditch Witch at Ditch Plains Beach, he starts his day at home, a modern glass house overlooking Lake Montauk, about a one-minute electric bike ride away.
He wakes up at 7:05 every morning without an alarm, and only gets out of bed after he clears his inbox. “Delete, delete, delete,” he said. “If it doesn’t make dollars, it doesn’t make sense. I’m in this game to win. I can’t lose. Failure isn’t an option.”
Geoff Gifkins, his manager at Nest Seekers, said that Mr. Eckardt has a knack for connecting with clients. “He comes across as brash and very off-the-cuff, but he’s a down-to-earth genuine guy and he does care about Montauk, his family and the kids in the community,” he said.
Mr. Eckardt helps clients, whom he calls “friends,” with things like landscaping and shopping. “I sell them a new house, and then they call me asking where they can buy sheets in town,” he said. “I’ll get you into the Surf Lodge, I’ll take your kid surfing. It’s a concierge service.”
Mr. Eckardt speaks as if everything that comes out of his mouth deserves its own Instagram post. Yet it’s not hard to see that his confidence can also serve as a facade.
One second he’s quiet, admitting that he cries in the shower and that his mother still does his laundry. The next, he’s name-dropping and talking as if he needs to be heard over loud music, looking around to lock eyes with someone he knows.
“I have a lot of anxiety, and I’m scared of everything,” he said. “I put on this persona. I put that guard up. Once you let someone in to see who you really are, they can use that to hurt you.”
Mr. Eckardt’s confidence was tested last summer. Just days after the Vanity Fair article came out, his career seemed to crater when his black Land Rover was pulled over on Montauk Highway for running two stop signs. His eyes were bloodshot, and there was an odor of alcohol and marijuana, according to the police report. He was arrested and charged with driving while under the influence of drugs; he pleaded not guilty. Nest Seekers put him on a leave of absence (he has since been reinstated).
At a January court hearing, he pleaded guilty to the lesser charge of driving while ability impaired. He also pleaded guilty to driving without a license and failing to stop at a stop sign. His license was suspended for 90 days, and he was fined $1,050 and had to do community service.
“I made a mistake that I will never make again,” he said. “You fall, you get back up. I needed that reality check. It humbled me. I was on my high horse.”
Indeed, Mr. Eckardt’s swagger and high-profile deals have led to some resentment, particularly among old-timers who think that he is aiding in the demise of Montauk as a salt-of-the-earth fishing community. Some local business owners have whispered that he is a sellout, though none would say that publicly, citing the decorum of this tightknit community.
Now, this small-town boy is getting bigger. Last week his publicist, Jessica Schaefer, confirmed rumors that Mr. Eckardt is to star in his own reality show this fall on Showtime. (A spokeswoman for Showtime denied that there is a show in the works.)
“It’s about a kid who comes from nothing in a small town,” Mr. Eckardt said. “I have a chance to show people in the Midwest, in London and Japan how I really hustle in the Hamptons.”
“I don’t want to be a reality star,” he said. “I’m here to build a brand.”
Back on his Montauk stroll, Mr. Eckardt passed A Wave Inn, a low-frills resort with a chain-link fence around the pool and small microwaves in each room.
It’s not for sale, but he is already thinking of a renovated pool and waiter service. He can already smell a fresh coat of paint. “It has the bones, but people don’t see it,” he said, putting his hands over his eyes. “It could be the next Soho House.”
“I’ve got blinders on,” he said. “I see one thing and that’s my future. I want it all.”
An earlier version of this article, using information provided by Dylan Eckardt’s publicist, misstated that a reality show starring Mr. Eckardt would premiere this fall on Showtime. A spokeswoman for Showtime said that no such show is in the works.