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Hamptons.com
April 11, 2025

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

David Andrewsby David Andrews
in Real Estate, Trending
Home Real Estate
Licensed Associate Real Estate Broker, Andrew W. Green (Drew Green)

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.

 

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Coveted Location in Quogue Village South

Coveted Location in Quogue Village South

  • The Hamptons have seen their fair share of collaborations and takeovers this summer. Still, nothing compares to The h.wood Group and Chase Sapphire Reserve’s transformation of Montauk hotspot Mary Lou’s into Delilah Montauk.⁠
⁠
The four-day takeover combined unforgettable dining experiences with show-stopping live entertainment featuring performances by Zack Bia, Alesso, Gwen Stefani, and DJ Pee.Wee (Anderson Paak). ⁠
⁠
Exclusively for Chase Sapphire Reserve cardholders, diners were treated to white glove hospitality and Delilah’s staples, including the famous chicken tenders and tuna tartare, and bold twists on Hamptons classics like lobster rolls, striped bass crudo, and crab and avocado toast. 

Check out more at Hamptons.com (Link in Bio)

#gwenstefani #alesso #djpeewee #chasesapphirereserve #delilahmontauk #montauk #hamptons
  • LVIS thrift shops are open Tuesdays through Saturdays 10 AM through 5 PM

donations are accepted Wednesday through Saturday 10 AM through 1 PM by appointment 

located at 95 Main St East Hampton
  • Check out the Top Hamptons Events This Weekend!⁠
⁠
🚗 The Bridge IX⁠
📅 Sat, Sept 13 | 2–7PM⁠
📍 The Bridge, Bridgehampton⁠
Over 300 rare automobiles showcased across stunning landscapes.⁠
⁠
🎬 23rd Annual Surf Movie Night⁠
📅 Fri, Sept 12 | 5:30–9PM⁠
📍 Southampton Arts Center⁠
Surfboard swap, live music & outdoor film screening. 🌊⁠
⁠
🍝 San Gennaro Feast of the Hamptons⁠
📅 Sat, Sept 13 – Sun, Sept 14 | 10AM⁠
📍 Hampton Bays⁠
Italian pastries, live entertainment & fireworks Sat @ 8:15PM 🎆⁠
⁠
🎭 In Process: Roderick George⁠
📅 Sat, Sept 13 | 7PM⁠
📍 Guild Hall, East Hampton⁠
A special in-process presentation of The Missing Fruit (Part I).⁠
⁠
🎤 Sheena Easton at WHBPAC⁠
📅 Sat, Sept 13 | 8PM⁠
📍 Westhampton Beach PAC⁠
Grammy-winning artist live on stage!⁠
⁠
☕ Cars & Coffee⁠
📅 Sun, Sept 14 | 9–11AM⁠
📍 Bridgehampton Museum⁠
Classic & exotic cars, food, drinks & live music.⁠
⁠
🛍 Hampton Vintage⁠
📅 Sun, Sept 14 | 10AM–5PM⁠
📍 Westhampton Beach Village Green⁠
Shop unique vintage finds!⁠
⁠
🎶 Hamptons Festival of Music Finale⁠
📅 Sun, Sept 14 | 4PM⁠
📍 St. Luke’s Church, East Hampton⁠
Featuring Cimarosa, Berlioz & Beethoven.⁠
⁠
🍷 Wine Dinner with Pradorey at R.AIRE⁠
📅 Tues, Sept 16 | 6:30PM⁠
📍 Hampton Bays⁠
Five-course tasting menu with exquisite wine pairings.⁠
⁠
🎥 Toy Story 30th Anniversary Screening⁠
📅 Sept 12–15 | Various Times⁠
📍 Southampton Playhouse⁠
Celebrate Woody & Buzz’s timeless adventure!⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#carshow #hamptons #sangennaro #sangennarofeast #winedinner #bridgeIX
  • The Animal Rescue Fund of the Hamptons (ARF Hamptons) hosted the Bow Wow Meow Ball in East Hampton. The evening’s honorees, Ellen and Chuck Scarborough, were presented with the Champion of Animals Award, recognizing their more than twenty-five years of support to ARF. ⁠
⁠
Over 400 guests celebrated ARF’s remarkable work with cocktails, followed by dinner catered by Olivier Cheng. Peter Marino, accompanied by his daughter and ARF Board Member Isabelle Trapnell Marino, presented the Scarboroughs with their award. ⁠
⁠
📸: Patrick McMullan/PMC⁠
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#arf #bowwowmeowball #hamptons #animalrescuefund #animalrescue
  • Make sure to add this event to your list for next summer
#Seafood #localeats #mtk #montaukgreen
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