Saltwater Roots, Real Estate Results: A Conversation with John & Jack Healey

In the Hamptons, some real estate agents wear loafers—John and Jack Healey wear waders. So, to interview Jack and John Healey, I met them where they are most comfortable: by the water. When they arrived, John, coming from the Bridgehampton Fire Department; Jack had spent the morning on the water fishing the Peconics. As their trucks pulled up, I was reminded of some ancient wisdom: You can learn a lot about a man based on his truck.

Take John Healey’s new model Bronco, which has a custom license plate that reads: SURFING. This is the truck of a man who appreciates style but has better things to do than tinker in his garage all day. His son Jack, meanwhile, drives a truck you’ll notice immediately—but don’t be fooled by the polish. It’s built for function, not show, and Jack puts it to work daily as a true bayman, oyster farmer, and lifelong Mariner.

With Jack recently joining Saunders & Associates, the Healeys are now a father-son team rooted in shared values, local knowledge, and deep community ties. John brings veteran experience and calm clarity to every deal, while Jack infuses the business with energy, innovation, and a homegrown authenticity that’s impossible to fake. I caught up with both of them to talk about how they work together, what they’re seeing in the market, and why real estate—like the East End itself—is better when it’s in the hands of people who truly live it.

Jack, where did you learn your gift of gab? Was it from your father?

Well, the apple doesn’t fall from the tree. But, I’ve been a caddy since I was 14, and nobody wants to have a caddy who can’t hold a conversation (or who knows when to keep quiet). Especially out here, I learned how to talk to people, regardless of how much influence or fame they have. But, beyond that, growing up at Wainscott School, you’ve only got 8 kids in a class, so you have to learn how to speak up because you can’t slip through the cracks.

John, what drives you as a real estate agent?

That’s a big question! But it comes down to curiosity—having a passion for knowledge. We’re in sales, and you have to know your product. So, I’m always asking questions and following up. The more information you have, the better I can advise clients and customers. I take the time to ask questions. It’s not just logistical. I’m curious about my clients’ lifestyles and goals, where they’re coming from and where they are going.

John, what originally attracted you to the Hamptons and made you want to raise your family here?

My family spent Summers in Quogue growing up in New York City, so I knew the East End. But, at my heart, I wasn’t a city kid – I had too much energy. Needed more room to roam and play! I always felt at peace in the Hamptons, loved that freedom and wanted to share that experience with my kids. It was so important to my wife and me that our family grow up around nature.

Jack, you’ve grown up on the East End and just joined Saunders to work with your dad. What’s it like stepping into the real estate world alongside someone so established—and what’s your own take on the business?

I feel confident, not just in my ability and knowledge, but also in the confidence that my father has in me. This isn’t a handoff; we are working together, and there is a mutual respect. He wouldn’t bring me on if he didn’t believe in me. I’ve watched my dad work my whole life, so there is a familiarity to how he operates. Really, though, I’m excited to put my skills to use—the computer and research side—the “job” part.

John, you’ve been a top producer for years. What excites you about this new chapter, especially working with your son?

I’ve never had a team before, so this is exciting. I operate on my own level, and that requires working with someone who can get it done, not get in the way. I’ve worked with assistants, but with Jack, there is a familiarity and trust with us that you can’t build overnight. We work great together, it’s seamless. Hamptons real estate moves at a fast pace, so I have no time to deal with confusion or lack of communication. I know Jack can handle whatever it takes.

How do you balance or complement each other when working with clients?

There is really healthy dialogue between us – I know that my father sees things in one way and that is built on experience and expertise. But, sometimes there might be a new tool or approach that can help amplify our marketing or better serve our clients. Having a back-and-forth is vital because I can learn why we do what we do, as well as help invite conversation about how we can build and expand our reach. We also have distinct viewpoints on any given problem, which allows us to be more creative in our approach.

The Hamptons market continues to evolve. Are there any trends, neighborhoods, or buyer behaviors you’re paying close attention to right now?

Well, waterfront is always king. I don’t just say that because I live on the water. That will always be the #1 driving factor. But it’s not just oceanfront. Having almost any waterview is like living with a moving picture. For me, North Sea is a real hidden gem in the Hamptons. The sunsets are unreal and make the South of the Highway people jealous.

Between firefighting, oyster farming, and community work, service seems to be a shared value. How does that mindset show up in your real estate practice?

Work in the community instills a “care” for my clients and customers, and really all areas of life. You see the human side, and that causes you to go the extra mile when working with someone. Especially with real estate, which involves inviting people into our community, we always see them as people first.

Jack, you’re deeply involved in sustainability and the local fishing culture. How does that shape the way you talk to clients about living—and investing—on the East End?

It starts with the understanding that the land and water on the East End are what make the Hamptons the Hamptons. There is a lot to protect, not just what is immediately visible. I help to share that passion and love for the area with clients. For me, it’s all about preservation, and I strongly believe there is a middle way so that development and preservation can co-exist.

What’s your approach to maintaining long-term client relationships in a high-stakes, high-touch market like the Hamptons?

Communication is key. I say that clearly because it is the single most important lesson for a real estate agent. Working with Jack is an extension of that because it doubles our speed of connection. Beyond communication, I come back to curiosity and maintaining an interest in other people’s lives – its important to be engaged and present so I can offer the best advise I can.