A Chat with Drew Green: An Approachable Real Estate Agent in The Hamptons

Drew Green is as much a part of the Hamptons real estate landscape as hedgerows and hydrangeas. A local icon with 28 years of experience, even if you aren’t familiar with Hamptons real estate (yet), you’ve likely been “shopping with Drew” at King Kullen, where he advertises on the shopping carts! 

Known for his wit, warmth, and uncanny ability to close a deal before you’ve finished your first cup of coffee, Drew brings a uniquely human perspective to the business of buying and selling. We caught up with him to talk landmarks, markets, history—and why you should always hire two bartenders.

The last time we spoke, you pointed out your “favorite tree in the Hamptons.” Do you have any other Hamptons landmarks our readers should explore?

So glad you remember that. Great tree! (It’s still standing, by the way—stronger than ever.) One spot I always recommend, especially if you love those quintessential Hamptons views, are the open vistas along Cooks Lane in Water Mill. It’s just off Scuttle Hole Road, tucked slightly south of the Atlantic Golf Club. The fields roll out in layers, with farmhouses dotting the horizon like they’ve been painted there. You get that sense of timelessness of the Hamptons. It’s a great little drive. 

You’ve experienced many different economic climates. How does the Hamptons real estate market track with the overall economic climate across the country?

Interesting question. In my 28 years, I’ve seen a lot: dot-com booms and busts, financial crashes, 9/11, and of course, the pandemic. What’s fascinating about the Hamptons real estate is that it often booms in times of major upheaval (9/11, Covid pandemic, etc.) I think it’s because people see (and rightly so) the Hamptons as a “safe haven” when world events make things seem uncertain.

After major world events—especially the ones that shift how people live and work—this market doesn’t slow down; it surges. After 9/11 and the pandemic hit, suddenly, people realized they needed an enclave and didn’t have to be in the city five days a week. They wanted space, air, and light. And we’ve got that in spades.

The Hamptons are what I call a “safety-value luxury.” When the world feels uncertain, people want a place that feels steady, beautiful, and grounded. And when things are booming? Well, they want to celebrate that here too. Either way—up, down, sideways—money moves when the world changes. And that leads to deals. Coming and going, going and coming. For agents, that’s activity. For buyers and sellers, that’s an opportunity.

Describe your perfect Hamptons weekend.

Easy: It starts with an early Saturday showing followed closely by a handshake deal—because nothing kicks off a weekend like a little real estate magic. Maybe an agreed listing pitch in the afternoon. Then I’m heading to a dockside happy hour—nothing too fancy, just something crisp in a glass and a view of the water. The day wraps with a beautiful dinner at home with my beautiful wife and maybe a house guest or two in our backyard. Lights twinkling, grill going, music low. That’s the Hamptons at its best—deals and dinners, all in a day.

You’re quite the history buff. As a Sag Harbor Village resident, can you share any interesting facts about Sag Harbor?

Absolutely—and just tell me when I’ve bored you because I can go deep here. Sag Harbor has this incredible backstory. Right before the Civil War, it was actually the second-biggest port of commerce in the entire United States. That’s wild when you think about it today. The whaling industry put it on the map, and a lot of that wealth and history is still embedded in the architecture, the street layout, even the vibe. You can feel it walking down Main Street. The Village is a living chapter of American history.

Anyone lucky enough to have been to your parties knows you know how to entertain. What are the keys to great entertaining in the Hamptons?

That’s easy: two bartenders with fast hands! 

READY TO MAKE YOUR MOVE TO THE HAMPTONS?

Give Drew a call—Just don’t be surprised if you leave with a deal and a great new trivia fact.

Whether he’s guiding clients through multimillion-dollar listings or giving you a Sag Harbor history lesson over a cocktail, Drew Green is exactly the kind of agent—and neighbor—you want in your corner. He knows the market, knows the terrain, and more importantly, knows how to keep things fun. Next time you’re at King Kullen, grab a cart and consider it your unofficial intro to the Drew Green experience.

To learn more about Drew, click here.