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February 26, 2023

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

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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6th Annual Battle of the Fantasy Girl Bands at the Talkhouse

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  • The 33rd Hamptons International Film Festival kicked off last Friday with the U.S. premiere of A24’s Eternity starring Elizabeth Olsen, Miles Teller, and Callum Turner.⁠
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Elizabeth Olsen attended the premiere on Friday, and on Saturday sat down with IndieWire’s Editorial Director Kate Erbland at the Sag Harbor Cinema as a part of the festival’s “A Conversation With” series. Later that day, the second “A Conversation With” took place as Ethan Hawke and moderator Alison Stewart talked about Blue Moon, as well as Hawke’s filmography. ⁠
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Sydney Sweeney received the festival’s Achievement in Acting Award following the U.S. premiere of her film Christy in East Hampton. ⁠
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Notable Guests included: Alessandro Nivola, Alec Baldwin, Amanda Peet, Tonatiuh, Miriam Shor, Lois Smith, Tim Blake Nelson, Mareille Enos, Bob Balaban, E. Jean Carroll, Roberta Kaplan, Ellen Barkin, Bernie Telsie, Bill Condon.⁠
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📸: Jess Dalene⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hiff #hamptonsinternationalfilmfestival #film #elizabetholsen #sydneysweeney #hamptons #hamptonsfilm⁠
  • When: Fri, Oct 3rd – Sun, Oct 5th, 2025
8am – 5pm

Where: Levain Bakery, 354 Montauk Hwy, Wainscott, NY

Levain Bakery is introducing a new cookie for a limited time: Peanut Butter Dark Chocolate Chip – a decadent mix of creamy and chunky peanut butter with rich dark chocolate chunks. Originally created to celebrate the opening of Levain’s Beverly Hills Bakery, this indulgent new flavor will now be available for just three days only, October 3–5, at all retail bakery locations.

To make the weekend even sweeter, guests who purchase a cookie will receive a Levain Bakery mini tote (while supplies last), a fan-favorite collectible sure to go quickly.

#levain #levainbakery #cookie #minitote #tote #hamptons
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🍪 Levain Bakery⁠
📅 Oct 3 – 5, 2025 | 8AM – 5PM⁠
📍 354 Montauk Hwy, Wainscott⁠
Try the Peanut Butter Dark Chocolate Chip cookie + snag a mini tote (while supplies last).⁠
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🎉 13th Annual SouthamptonFest⁠
📅 Oct 3 – 5, 2025 | 10AM – 7PM⁠
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Arts, culture, food & family fun all weekend long!⁠
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🎶 SpringsFest⁠
📅 Oct 4, 2025⁠
📍 1 Parsons Pl, East Hampton⁠
Live music, raffles, crafts, blacksmith demos & more.⁠
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💃 Salsa Social @ The Clubhouse Hamptons⁠
📅 Oct 4, 2025 | 9PM – 11:30PM⁠
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Dance the night away w/ DJ Chile & more!⁠
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🐚 34th Annual Largest Clam Contest⁠
📅 Oct 5, 2025 | 12PM – 3PM⁠
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Taste clam chowder, clam pies & cheer on the winners!⁠
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  • So many fun fall activities in the Hamptons 🎃

@fairviewfarmatmecox 
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#hamptons #fall #applepicking🍎 #pumpkin #maze #pettingfarm
  • As summer winds down and the cool breezes of fall approach, jewelry enthusiasts and fashion lovers alike are looking for the latest seasonal trends. Yael Fraynd, founder and president of Yaya Publicity, offers an insider’s perspective on what to expect this fall — especially for those embracing the chic lifestyle of the Hamptons.⁠
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Looking ahead to fall, Fraynd described the evolving styles with enthusiasm. For fall, expect to see bold statement pieces, rich gemstone colors like orange and a playful mix of metals. ⁠
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She also noted the influence of pop culture on jewelry trends, including celebrities like Taylor Swift, who is recently engaged, saying, “It could also be just, you know, with Taylor Swift, who has such a big effect on what people like.”⁠
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On the seamless transition from summer to fall styles, she observed, “In the summer, you see a bit of Western-inspired pieces, and I think that they really do kind of transition into fall really nicely. ⁠
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Read the full article at Hamptons.com (Link in Bio) ⁠
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#fall #falltrend #falljewelry #hamptons⁠
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📸: Danté Crichlow for The Apollo⁠
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#apollo #apollotheater #hamptons #easthampton #benefit #fundraiser
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