Get Ready for Real Estate Drama: ‘Selling the Hamptons’ Season Two Comes to Max on March 1

Ashley Allen is not shy about her opinion of “Selling the Hamptons.”

After watching season one of the reality television show — which centered on not only the real estate, but also the drama, within a Southampton-based Nest Seekers International team — she said she found it flat and, at times, simply boring.

So when its producers approached her to join season two, she had one condition: It needed to be more fun.

“And they listened,” she said. “There are a lot of daggers that come out, there’s a lot of awkward situations. It’s just going to be really good.”

On March 1, the familiar cast of characters — including Bianca D’Alessio, J.B. Andreassi, Peggy Zabakolas, Mia Calabrese and Michael Fulfree, as well as a few new faces — are officially back and fierier than ever, competing for the hottest listings in one of the most aggressive markets the East End had ever seen.

In the wake of the HBO Max and Discovery Plus merger, “Selling the Hamptons” — which streamed on the latter — was put on hold, Andreassi explained. And so, season two is a step back in time to 2022, he said, and will air on the combined streaming service, Max.

“Knowing that it was filmed two years ago, so much has changed since then, but what remains the same is the high stakes and high pressures of being an agent and a broker in a place like the Hamptons,” he said. “That’s always going to remain the same. The properties switch out, the owners switch out, but that underlying stress-filled environment remains constant.”

While the market and trends have ebbed and flowed, and some homes have even exchanged hands again since filming, what has also stayed consistent is the “boys club” barrier in a male-dominated industry — walls that Zabakolas fights to tear down both on screen and off, she said.

“I tried to show myself, but also show others — young females and a lot of the girls that I mentor — that you can do it and don’t take no for an answer,” she said. “And just because, yes, more things are being thrown at us than they should be, we can show them how to do it and I will probably do it better than any other man — and I’ll be wearing my 5-inch heels.

“I don’t want to represent women, but I hope that I show girls that we can do it,” she continued. “In our society, girls are raised to be quiet and silent and polite and to appease people, but that suppresses our wants and needs — and why can’t we do it? At the end of the day, we do it 10 times better than most men.”

In season two, Zabakolas said she transitioned from people-pleasing — by leaving money on the table — to going after every opportunity for herself, which undoubtedly ruffled some feathers.

“The most challenging part of filming this season was seeing certain people’s true colors,” she said. “I’m seeing that money trumps character.”

Also shaking up the team was the arrival of Dylan Eckardt, dubbed the “Bad Boy of Real Estate,” who is known for selling some of the most iconic estates on the East End and beyond to celebrity clients.

“This guy coming out here to the Hamptons is my worst nightmare,” Fulfree says in the season two trailer.

But Eckardt is also known for stirring the pot — which is, by far, Andreassi’s least favorite part of shooting the show.

“I’m someone that kind of tries to steer away from that part of things,” he said. “I think it’s inevitable in our business and that’s definitely reflected, I think, in TV shows like this. I think my favorite part is just being able to highlight and showcase some of the most beautiful homes in the country that we’re so lucky to be a part of in the Hamptons.

“This is my home,” he continued. “This is where I was born and raised, and just to be able to showcase the beautiful beaches, the wineries, things that make the Hamptons so special and put that on for the world, essentially, is really cool — just to be able to be that ambassador of my home. And I think that’s the best part of doing this.”

But try as he may, Andreassi found himself dead center amid the drama, from the moment Allen walked into the office to shake things up.

In season one, she made a guest appearance — “I was the one that gave J.B. my bush,” the owner of plant shop Seedybean said, referencing a literal plant — and kicked off season two by jokingly trying to sit in her co-worker’s lap.

And casually mentioned that she — the daughter of Jeff Allen, managing partner of South Fork Custom Home Development — intended to take over her father’s opulent, $50 million portfolio, which Andreassi largely represents.

“I definitely make him really uncomfortable,” Allen said of Andreassi. “To me, I find it hysterical and I don’t know if it’s a girl thing or a J.B. thing, but the more uncomfortable that he’s going to become, the more I’m going to push him because I just find it so funny. Maybe I’m mean, I don’t know.”

For both Allen and Zabakolas, the unlikely friendships and alliances they made were some of the best parts of the second season, she said. As for a third season? Talks are not yet underway, Andreassi said, but he remains optimistic.

“From all indications, this is by far the best season we’ve filmed,” he said. “I hope that’s the case and I think it is. I remember it being very fun. It was a drama-filled season and I think it’s gonna come off really great. We’re excited.”

“Selling the Hamptons” season two will premiere on March 1 on Max. For more information, visit max.com.