‘Selling The Hamptons’ Season 2 Brings New Castmembers to the Real Estate Drama

On the second season of Max’s real estate reality show Selling the Hamptons, bad-boy agent and new castmember Dylan Eckardt reveals to the cameras regarding his castmates: “I barely like them at all.”

In another scene, agent Peggy Zabakolas walks away from a team get-together and says to her fellow agent (and onetime singer) Ashley Allen, who’s also a new castmember, “Let’s try to stop calling other women bitches.”

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Amid the setting of the Hamptons home market — a residential fantasyland of mega-mansions expressly designed to engender a relaxed second-home vibe — the drama on the show includes accusations of trying to steal listings from each other, tensions over nepo babies in the biz and even an open house, led by castmember Mia Calabrese, at a residence where construction isn’t completed. As guests sip drinks, workers are going full tilt with their drills trying to finish the residence in time for the summer season.

The show features a team of agents who all work for Nest Seekers International, founded in 2002 by Eddie Shapiro, who cameos on the show. Among the cast are former model Michael Fulfree (who spoke to US Weekly recently about his 80-pound weight loss journey since the second season aired); his long-time good friend JB Andreassi; and Bianca D’Alessio, whose selling home base is New York City. Some of the castmembers originally appeared on the Netflix show Million Dollar Beach House, prior to joining Max’s Selling the Hamptons.

Selling the Hamptons - Cast
A scene from Max’s Selling the Hamptons, with (from left) Bianca D’Alessio, Mia Calabrese, Eddie Shapiro and Dylan Eckardt.

“It’s a very exciting season. We have a lot of new personalities, a lot of new characters and amazing properties,” says Shapiro, who speaks with THR about the dynamics on the show, how the series originally came together and what Hamptons house would be his dream listing.

What have been some of the highlights of Selling the Hamptons so far for you?

In season 1, there were multiple things that took place — like introducing and bringing a few more of the New York brokers into the Hamptons. There’s some interesting tension that happened both on and off camera. It’s kind of a funny relationship that happens between the New York City brokers and the Hamptons brokers where they kind of need each other and they network a lot and they work together, but on the other hand they don’t want either side to come and step into their world and kind of cannibalize their business. The New York City brokers will come in, spend a summer there, make noise and then leave once October comes. It’s an interesting dynamic where we’re friends but we’re also frenemies. We’re very good friends — as long as you don’t come to my backyard and start doing business locally.

Eddie Shapiro - Nest Seekers International - President and CEO
Nest Seekers International president and CEO Eddie Shapiro

What can viewers expect to see on the show when it comes to houses?

Houses that are anywhere from three to four million, which would be a bit of a starter home these days in the Hamptons, to as much as a $150 million waterfront estate. This is probably one of the most expensive properties ever been shown on these shows. It really covers the Hamptons from top to bottom.

Selling the Hamptons - Real Estate - Property
A property featured on season 2 of Selling the Hamptons.

What do you like about doing the show?

I love watching our brokers — most of them are a younger generation — develop and evolve and grow in the business. I love watching their brand develop and watching them go from young aspiring brokers that are just trying to survive and make a living to becoming household brands. I’m very invested in the individuals; it’s always been my thing in the industry.

Do you know yet if the show is confirmed for a third season on Max?

I’m not authorized to say.

How did Selling the Hamptons first come about?

Well, Nest Seekers has been in media for the better part of the past 15 years with Million Dollar Listing on Bravo [which starred former Nest Seekers agent Ryan Serhant] and that has continued to be a part of our journey and living in that space, not just as a brokerage firm but more as a lifestyle brand. Real estate is a constantly growing genre in the world of television and media and I guess they keep coming back for more. About five or six years ago I believe the conversation started with a production company. There were initial concepts of what would a real estate show about the Hamptons look like. We kept kicking around different ideas and eventually landed on just featuring this young group of brokers just forming into a team in the Bridgehampton office — Bridgehampton being the center of the Hamptons and that’s how it started. Actually it started with Netflix and it evolved and eventually landed again with Max, and that’s where we are are today. There are a lot of shows that have been made about L.A. — Selling Sunset, Buying Beverly Hills, Million Dollar Listing LA — but there’s never really been a show about the Hamptons except for our show. I think that makes it unique and different and interesting because it’s not a world that has seen cameras so much. It’s a little bit more of a secretive enclave.

Do you have a dream house listing in the Hamptons?

There is one house that if it ever hits the market, it would likely list somewhere between 500 to a billion and it’s [businessman] Ira Rennert’s great estate Fair Field in Sagaponack. I would say it’s everyone’s favorite not just mine. He built it over a number of years. It’s about 64,000 square feet and I think it has something around 70 bathrooms. It’s probably the most expensive house in America.

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