THE MAN WHO ATE MONTAUK . . .

. . . Is also the guy who saved it. Meet Dylan Eckardt—surfer, party boy, and real-estate agent to the stars.

“I’m being very, very good with you today,” Dylan Eckardt said to me one recent morning as he careened his Range Rover around a curve off of Montauk Highway. We were headed to Gurney’s, the historically Wasp-ified hotel on the eastern tip of Long Island, when Eckardt had conceded to dispense with his habit of texting while driving. For the morning, anyway. Cops had already written him seven tickets in the last two months, he told me. “All the cops know who I am,” he said as he pulled into a parking lot and proceeded into an illegal spot. “No one is going to say shit to me.”

Eckardt, with his tousled, sun-streaked hair, has a reputation among the locals of Montauk. He is loudmouthed and wide-eyed, a former pro surfer and unofficial bouncer of the local surf beaches. But Eckardt had an epiphany a few years ago that he wasn’t going to make money forever off of riding waves. Instead, the Montauk native envisioned another wave breaking down upon the sleepy fisherman’s idyll where he grew up. Montauk had been lurching ever rapidly away from its lobster-shack roots as it began resembling the other hamlets of the Hamptons.Now there was a swell of Wall Street guys and Lululemon moms. People wore fedoras and drove Teslas. Montauk, the land of blue-collar fishermen, had become the province of nightclub promoters.

The locals were, of course, outraged. But Eckardt had a different response. He wanted to get in on the action. So he found a new calling—real estate—and joined Nest Seekers, the upscale boutique realtor, where he soon went into overdrive expediting the development of what remained of the quaint town. In his first four months, he brokered the deal for a Montauk establishment that had been on the block for half a decade and sold $10 million worth of property. Eddie Shapiro, the founder of Nest Seekers, told me that clients have described Eckardt as “totally nuts” and “an acquired taste.” But this is real estate, not social work, and only one thing matters. “They don’t know how he does it, but he does it,” Shapiro told me.

Real estate is a business built around who you know, after all, and no one has better connections around town than Eckardt—the man who says he is widely believed to be the inspiration for Cole Lockhart, Joshua Jackson’s character on The Affair. He’s in the water with town cops he went to high school with at dawn, he sweats on the elliptical at Gurney’s next to local contractors, and he rolls up to barbecues at the oceanfront homes of young tech billionaires, probably with a harem of pretty blondes who teach yoga and dance cardio classes, when the sun goes down.

“He has a different style. You’ll surf, and he’ll get everyone to be nice to you,” said Jon Krasner, a client and New York–based real-estate developer who has bought a handful of local mom-and-pop establishments to convert into hipper restaurants. “He’s got good at relationships. That doesn’t mean he’s good at underwriting deals, but that’s a huge advantage that these hedge-fund guys don’t realize. In these small-town communities, if they don’t want you to develop something there and you’re from Manhattan, you’re not developing something there.”

In some ways, Eckardt seems cognizant of this newfound status. After we arrived at Gurney’s, he walked out of the Range Rover and took a gander at the ocean rolling into shore before heading into the gym. “There’s nothing like me,” he said, tucking his shaggy hair behind his ears and maneuvering toward an elliptical machine. “I dress like a fashion kid from the city, I talk like an asshole, and I surf like a local. I’m the fucking rock star of real estate. I’m the fucking prince of Montauk."