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Hamptons.com
February 26, 2023

Sixty-Something: Hamptons 54-Mile Gold Coast of Multimillion Dollar Homes

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VIEWS
T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
Sixty-Something: Hamptons 54-Mile Gold Coast of Multimillion Dollar Homes

Recently a New York City tabloid once again wrote about the Montauk Trailer Park on 180 DeForest Road. Officially known as the Montauk Condominium Association, a unit (trailer) there, located near the ocean shore of Ditch Plains, was sold for a reported $3.7M. I actually once lived in a rented room in that complex for 3 years. The paper called it, “Billionaires Trailer Park.” When I lived there it was everything but. In a real estate column, named, “Estate of Mind,” I once wrote, “There are not enough trophy homes for the real winners in life.” Now I know for sure there really aren’t.

 

Recently, I decided to personally survey the Hamptons Gold Coast! It’s winter, my sailboat is on the land so I had the time to explore. Driving from the Montauk Lighthouse to where the ocean shore of the Hamptons ends on County Road Route 89 at Cupsogue Beach CountyPark was fun. This park is just west of Westhampton Beach and the Village of West Hampton Dunes. The whole drive measured 54 miles on my GPS.

 

Having spent the last twenty years traversing the Hamptons to get to my sailboat in EH, I actually never traced the whole Hamptons ocean shoreline. I did it this week. There are private roads not truly available to drive on but, knowing the areas, I stayed as close as I legally could. What I saw was very humbling. The whole 54 miles is lined with multimillion-dollar most likely “second homes.” I can’t really estimate the sum of the value of all the homes, but I am sure it’s well into the billions.

 

I never knew of the beach clubs on the ocean between Hamptons Bays and Westhampton Beach. There is even an oceanfront senior living condo complex. Then there are also various tennis clubs. Notables are the grass tennis courts of both the Meadow Club of Southampton and the Maidstone Club of East Hampton. However, around Westhampton Beach there are others with both hard surfaces and with Har-Tru, a crushed pebble fast-drying surface. Many of the multimillion-dollar homes also had tennis courts. I never enjoyed playing tennis with a strong offshore breeze, but I guess I could learn to.

 

Some homes, like the ones in Wainscott, are actually farms while others built along the dunes seem like Star-Trek complexes. Folks, like billionaires Ronald Perlman and David Geffen, have very impressive spreads on the ocean. Estates that you can’t really get that near to. One time, my wife Cindi and I attended a function at Jerry Della Femina’s oceanfront home. It was an ocean address right off Lily Pond Lane. We were conscious of not bringing sand into the house. Walking from the ocean right into the living room is cool. When one has pets, keeping the sand out of the house is probably a losing battle. Back in the day, my beagle brought in plenty of sand at the Montauk trailer 432 steps from the breaking waves of Ditch Plains.

 

The literal opulence of most of the homes is astonishing. Obviously, there are people of means who want an oceanfront home. How many trophy homes are there going up along the thousands of miles of both U.S. ocean coasts? There are lots of folks of means in this country; all these multimillion-dollar homes proves it. I guess most are so smartly well-off that they are not worried if a Hurricane Sandy comes along and destroys their oceanfront home. One has to conclude that’s what being able to afford good insurance is all about.

 

Doing some east end journalism for twenty years has given me the opportunity to be invited into some of these homes. All I can say is that my first impression when being led to the decks, balconies, and grand rooms with the amazing ocean views is “wow!” In the summer of 2007, I was on a patio off the ocean of a Further Lane, EH home. I was talking with then Presidential Candidate, Senator John Edwards. His wife Elizabeth was by his side along with perhaps twenty notables including a Beatles ex-wife, a star of Sex in the City, and a hip-hop mogul. I still remember almost every detail of that day 15 years later. Being an easy story to write up, it was a peek into what goes down in these mammoth ocean homes perhaps on most summer weekends.

 

Lastly, I thought I’d conclude with this truly Hamptons story. One time at an event I was sipping a beer with a gentleman and his wife who were groundskeepers for some folks who owned a genuine Hamptons oceanfront mansion. They lived in a cottage on the grounds. They kept the home in pristine condition all year ’round. The elderly owners hadn’t been around for a few years. Yet, they telephoned in almost daily to ask about the home, the plants, and the weather there.

 

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  • It’s Fourth of July Weekend! ⁠
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Check out our guide to all the fireworks displays set to dazzle the Hamptons. ✨⁠

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🎇 Stars Over Montauk Fireworks by Grucci⁠
📅 Saturday, July 4 | 9 PM⁠
📍 Best viewing from Gosman’s Dock & Gin Beach, Montauk⁠
Bring a blanket or beach chair and enjoy one of the East End’s most spectacular fireworks shows.⁠
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🚢 Fourth of July Fireworks Cruise aboard the Viking Classic⁠
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⁠
🎆 Devon Yacht Club Fireworks⁠
📅 Friday, July 3 | 9:15 PM⁠
📍 View from Fresh Pond Beach, Amagansett⁠
Although the event is private, the fireworks can be enjoyed from nearby Fresh Pond Beach.⁠
⁠
🎇 East Hampton Fire Department Fireworks⁠
📅 Saturday, July 4 | At Dark⁠
📍 Main Beach, East Hampton⁠
A beloved annual tradition lighting up the skies over Main Beach.⁠
⁠
🎆 Westhampton Country Club Fireworks⁠
📅 Saturday, July 4 | 9 PM⁠
📍 Westhampton⁠
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⁠
🎡 North Sea Fire Department Carnival Fireworks⁠
📅 Thursday, July 2 & Saturday, July 4 | At Dark⁠
📍 Firemen’s Field, Southampton⁠
Enjoy carnival rides, games, food, and two nights of fireworks.⁠
⁠
🎇 Sag Harbor Yacht Club John A. Ward Fireworks⁠
📅 Saturday, July 4 | 9:30 PM⁠
📍 Marine Park, Sag Harbor⁠
Don’t forget to tune into WLNG 92.1 FM for the synchronized fireworks soundtrack!⁠
⁠
✨ The Clamshell Foundation Fireworks Over Three Mile Harbor⁠
📅 Saturday, July 11 | 9 PM⁠
📍 Three Mile Harbor, East Hampton⁠
Keep the celebration going with this annual summertime fireworks display.⁠
⁠
🎆 Shelter Island Fireworks Spectacular⁠
📅 Saturday, July 11 | 9 PM⁠
📍 Crescent Beach, Shelter Island Heights⁠
A favorite community tradition overlooking beautiful Crescent Beach.⁠
⁠
#fourthofjuly #hamptons #fireworks #montauk
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One of the restaurant’s most famous dishes is its legendary chicken entrée, served with perfectly prepared vegetables and creamy mashed potatoes. It’s the kind of dish that keeps people coming back again and again for lunch. Chicken is one of the hardest dishes to make in my opinion, especially if it’s not fried, and this one is flawlessly executed every single time.

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🎤 Snoop Dogg at The Surf Lodge⁠
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Kick off your holiday weekend with sunset views, cocktails, and a live performance from Snoop Dogg.⁠
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👠 Stuart Weitzman Pop-Up⁠
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✨ Glacē™ by Candela at The HUB⁠
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☕ Ralph’s Coffee at Mulford Farm⁠
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🎨 Bridgehampton Art Affair⁠
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🖼️ The Cadence of Form Exhibition⁠
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🇺🇸 Which event are you checking out this weekend?⁠
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  • GUIZIO x ESSX x Montauk General Pop-Up
 
When: Fri, July 3rd – Sun, July 5th, 2026
11am – 6pm

Where: ESSX, 53 The Circle,
East Hampton, NY

NYC-based fashion label GUIZIO will be popping up at ESSX East Hampton, bringing a curated assortment of the brand’s latest arrivals and bestselling styles to the Hamptons 
 
#guizio #essx #hamptons #easthampton #popup
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