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Hamptons.com
October 7, 2023

Sixty-Something: Living Out Your Dreams on the East End

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VIEWS
T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
Sixty-Something: Living Out Your Dreams on the East End

Throughout my life, I have heard the word “dream” used in many ways: dream job, dream house, dream car, dream date, and so forth. When you reach your sixties and beyond, you start making decisions to perhaps take aim and achieve some of your dreams. Over the last twenty years, I have watched so many people actualize living out their dreams on the East End. We all know the stories of dreams coming true on the East End.

 

Ever since there was a 1960s TV show called “Route 66,” I have desired a 1963 Corvette. Of course, at this late stage of life, I can actually buy one, I just never will. I have actually only driven in a Corvette once in my life, and disliked the ride; the same thing with Porsches and Ferraris. They ride too tight and hurt my ribcage. I find it ironic how many folks my age are now owning and driving brand new Corvettes and Porsches, realizing it’s now or never.

 

On the East End, I believe there seems to be a trend of successful people late in their lives who have decided to invest all their time and resources to concentrate on their dream of painting, doing photography, playwriting, or trying to finish a novel. The energy from the natural beauty of the East End seems to inspire many folks to be creative. I know I am one of those folks. In the Hamptons, it does seem normal to have a judge and a few town supervisors who, besides their jobs, just love to be up in front of people singing and playing live music all over the East End. Quite frankly, they are all talented. It’s not just local politicians who have the musical bug. Up until these last few years, billionaire Ron Perlman of Revlon had a yearly blowout party at his Wainscott estate named “The Creeks” to help raise money to support the Apollo Theater in Harlem. He would have first-rate talent from Jon Bon Jovi to Blake Shelton at these parties playing songs and performing with a huge fun jam, usually with him on the drums!

 

The dock in Sag Harbor in the summer has a lineup of multi-million-dollar yachts, often with a car or helicopter mounted on them. I guess for folks like Johnny Carson, having their multi-million-dollar yacht docked in Sag Harbor was a dream realized. I remember sailing one afternoon in Gardiner’s Bay and seeing a huge superyacht anchored in the middle of the bay. Suddenly, my sailing buddy Todd pointed to a helicopter in the sky, and then in total amazement, we both watched it hover over the top level of this megayacht. While this helicopter poised off the top deck, a man in a business suit with a briefcase disembarked from the helicopter and walked onto the boat as the helicopter flew away. I still have the video footage on my iPhone!

 

Folks have different dreams. When I was a very young man, a close friend told me while sipping a beer that his dream was to have his wife’s name on his private jet and his girlfriend’s name on his helicopter and have them shop together in Milan buying him clothes. The funny thing is this same dude has been married to the same woman for 50 years now. Funny what true love can do to dreams.

 

I remember a few years back the trend was to buy Bridgehampton horse farms. Madonna and Matt Lauer were two names I remember who bought horse farms in Bridgehampton in that era. I know I have often driven the back roads admiring those horse farms. They are trophy properties of the Hamptons.

 

I was actually assigned to cover a property being sold to the Village of East Hampton that had huge sculptures on it. At that time, Sasson Soffer, an 80-year-old world-renowned artist who lived in Amagansett and New York City, owned some wooded land off Town Road. I believe over the 19 years he owned the property, he had placed 30 of his large and small sculptures there. I actually went and inspected them. His plan was for a town-owned sculpture park that would be named Grandeland. He only wanted six of his sculptures to be the only artwork displayed. Mr. Soffer’s arts foundation was to pay for installing and maintaining the sculptures. The town bought the land in 2006. Different folks have different dreams.

 

I am now living out my dream of sailing, writing, reporting, and enjoying being a husband and grandfather. I am now, like so many others, living out my dreams on the East End.

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Whether you receive Dria Murphy's iconic newsletters or catch her segments on the Today Show, she is the wellness curator. Dria welcomed founders, editors, creatives, and premium members of the by dria community for a day of connection, movement, beauty, and wellness at the Shou Sugi Ban House in Watermill. 

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On Saturday, July 11, God’s Love We Deliver (GLWD), NYC’s premier provider of medically tailored meals and nutrition education and counseling for individuals affected by serious illness, held its 25th annual Midsummer Night Drinks event at the East Hampton home of Culinary Council member David Burtka and husband Neil Patrick Harris. The event raised over half a million dollars supporting GLWD’s crucial work, one of the most successful Midsummer Nights Drinks to date.

Neil Patrick Harris and David Burtka Host Hamptons Midsummer Night Drink Event Raising Over $500K

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Over the past week, there were 21 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 20 Listings that went into contract.




Which is a year over year INCREASE of 5%.

This same week in 2024, there were 28 Listings that went into contract.

Compared to this past week, there was a DECREASE of 25%.

Hamptons Real Estate Market Data – Week of 7/14/2026

Over the past week, there were 21 Listings that went into contract from Westhampton to Montauk.

Compared to this same week last year (2025), there were 20 Listings that went into contract.

Which is a year over year INCREASE of 5%.

This same week in 2024, there were 28 Listings that went into contract.

Compared to this past week, there was a DECREASE of 25%.

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  • Sant Ambroeus has become one of the East End’s most beloved dining destinations. The place has style, serves gelato and espresso all day, offers inviting outdoor seating, and delivers a world-class dining experience.

Their fresh pasta is made with eggs, and doesn’t weigh you down like other pasta does. The signature branzino dish has become a calling card for the Southampton location.

No visit is complete without a stop at the gelato counter, where handcrafted gelato and sorbetto are churned in-house, offering a cool, classic finish to a summer meal.

You’ll see me there again sipping an espresso and pretending to be Italian. Diet starts tomorrow.
  • Ralph’s Coffee is popping up at Mulford Farm for the summer season. Stop by from 8am - 5pm for specialty drinks, pastries, outdoor seating, and lawn games until September 7th.
@ralphscoffee 
#Popup #ralphscoffee #coffee
  • Today, @childrensmuseumoftheeastend hosted its 16th Annual Family Fair in Bridgehampton, raising funds for its on-site food pantry, providing summer camp scholarships to local children, and supporting other initiatives that serve East End families year-round.

A special thank you to CMEE and lead event sponsor Saunders & Associates for welcoming us to capture the day’s magic.
  • We stopped by Pre-Loved in Montauk to see where founder @sunnymelet sources her vintage pieces. You can visit Pre-Loved any day of the week from 10am - 6pm.
@prelovedmtk
  • Last week, Rebecca Minkoff, alongside RummiKlubLA founders Laura Galvan and Marnie Wekselblatt, celebrated the launch of their first collaboration, a limited-edition blue terrycloth RummiKlubLA game set, with a Hamptons-style game day at the picturesque Maidstone Inn in East Hampton.

The limited-edition game set features a vibrant cobalt-blue terrycloth carrying case, playing pieces, and racks featuring the signature Rebecca Minkoff logo. The set feels luxurious and is a summer essential.
@rebeccaminkoff @rummiklubla

#rummikub #rebeccaminkoff #easthampton #maidstone #collab
  • If you’re into Mediterranean cuisine, Calissa is the spot for you. From the moment you arrive, you’re greeted with complimentary valet parking, amazing front-of-house staff, and an oasis of Greek fine dining. The place runs like a jet engine: an open kitchen, sexy interior, an energetic environment, a long bar, and an enormous outdoor dining area.

We sat down and started with the Saganaki, the world-famous fried Greek cheese. They do it right at Calissa: coated in sesame seeds and drizzled with fresh honey, the dish is a flavor bomb. I recommend ordering the steak here, it comes out cooked perfectly with fresh tomatoes. We also tried the grilled octopus, which is listed as an appetizer but could easily stand in as your entrée if you’re looking to eat a little lighter that evening.

If you feel like dancing, the restaurant transforms into a lively bar after 10pm making for a real Hamptons memory. The entire evening at Calissa is special. Highly recommend.
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