Stephen Penta has a hard time relaxing. And during those rare moments when he does slow down, the videographer won’t be found sitting still on a sandy beach.
A self-proclaimed “neurotic New Yorker,” Mr. Penta has never understood the Hamptons appeal, nor visited. Until this summer. So when he agreed to shoot and direct a new campaign for Douglas Elliman Real Estate—a series of short videos that explore the hamlets and villages across the East End—he arrived in Southampton not knowing what to expect.
He had a number of preconceptions, he admitted last week in an email interview, after having visited his fair share of mind-blowing locations through his line of work. But it didn’t take long for him to realize that the East End was unlike anywhere he’d ever been. And, unexpectedly, he felt a sense of nostalgia for his hometown in Amish Country, Pennsylvania.
“I didn’t expect the small-town feel and sense of strong community among the locals,” he said. “Being a small-town boy at heart, that really resonated with me, and I think it shows in the pieces.”
The series begins in Southampton Village—an obvious choice for Douglas Elliman marketing coordinator, and series producer, Luisa Keszler. It is where the 22-year-old grew up.
She gave Mr. Penta the grand tour, bringing him to the beaches, around Main Street and through the estate section.
“There are very few places with such a high concentration of homes that feel like works of art in themselves,” he said. “And being able to tour them and talk to owners about their history … so cool.”
Exploring the East End’s artistic legacy, they made a stop at Keszler Gallery, owned by the producer’s father, Stephan.
“When I saw this the first time, I thought, ‘This is the way a village should be when you dream about this,’” Mr. Keszler recalled in the video. “The first day I came here, I was so much in love with the Hamptons that a day later, I bought my first house.”
It is a place for culture, he said. It is a place for free spirits. And it is a place to be creative.
“At first, he did the interview to help me out with my first project,” Ms. Keszler laughed about her father’s participation in the shoot last week during a telephone interview from her Manhattan office. “After seeing how the video turned out, I know he’s shared it with all our friends and family, and not just because he’s in it. Because the video just captures Southampton so well.”
The video, which was released in August on Douglas Elliman’s Facebook page, begins with a sunrise on the beach. A mail truck drives down Wyandanch Lane, the music cues up—giving Ms. Keszler goosebumps every time she watches, she said—and the camera takes off through the village.
By the end, the sun is setting over Shinnecock Hills Golf Club to a voiceover by Flying Point Surf Shop sales associate Kevin McCabe.
“The cool thing about Southampton is anywhere you go to see the sunset, it’s gonna be amazing,” he says.
The 3-minute segment is not necessarily selling real estate, Ms. Keszler emphasized. It’s promoting a lifestyle.
“There’s nothing out there like this, from our point of view,” she said of the video campaign. “People really trusted me and trusted that we weren’t going to have them selling houses.”
Over the course of a week, Ms. Keszler and Mr. Penta filmed hours of footage—frequenting scenic destinations and dropping into local businesses. They chatted with Mr. McCabe about surf culture and Tate’s Bake Shop owner Kathleen King about cookies, which she began baking and selling at age 11 on her father’s farm in North Sea.
Ms. King said she has watched the community ebb and flow with modern times, but certain elements will remain constant: the air, the smell, the light and a sense of camaraderie.
“We always had the ocean beaches and rode our bike anywhere and it was very innocent and wonderful,” she reminisced in the video. “Being in an area like this, we have a large metropolitan influence, everybody’s always on, ‘What’s the new thing, what’s cutting edge, what’s everybody want?’ And it’s funny because, of course, my family, we all laugh and I tell my father, ‘You know what, Daddy? Everybody wants to go back to how we used to live.’”
As the video series continued through Bridgehampton, Sag Harbor and Montauk, Mr. Penta found himself identifying with the farm stands, one-room schoolhouses and high-end restaurants—such as Nick & Toni’s in East Hampton—that grow their own organic ingredients, he said.
Through most of August, he traveled from village to village with Ms. Keszler, talking to locals about what they love most and seeing the sites themselves: Banksy walls in Southampton, the Home Sweet Home Museum in East Hampton and the Pollock-Krasner House & Study Center in Springs—Mr. Penta’s stand-out visit thus far.
“It’s all been pretty fantastic. I’m creative at heart, and I love talking to artists about their creative process,” he said. “So getting to spend time talking to the director, Helen Harrison, who’s just so sweet, and getting to tour the workshop was a big highlight for me,” he said of his visit to Jackson Pollock’s former home and studio space.
Next up, Douglas Elliman plans to explore Hampton Bays, Westhampton and the North Fork once it releases the Bridgehampton segment, Ms. Keszler said. Locations farther east, where the film-making duo learned about the yachting community and the intricacies involved in catching lobster, are slated to be released.
“I found myself on a lobster boat in Montauk, talking to someone about putting rubber bands on the claws,” she said. “I’ve never experienced something like that. I found places I never would have gone if I had not been doing this video. Even though I’m a local, I still have learned so much throughout the whole project.”
And so has Mr. Penta.
“I didn’t get the Hamptons before I did this project,” he said. “And now I get it.”