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Hamptons.com
August 28, 2023

Sixty Something: Celebrate Your Success

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T.J. Clementeby T.J. Clemente
in Community, Trending
Home Community
Sixty Something: Celebrate Your Success

What is better than the sweet feeling of success? It comes in many different forms, such as financial, family, sports, and scholastic achievement to name a few. According to historian Dumas Malone, Thomas Jefferson, while sitting in the newly constructed White House, stated that his brother Randolph was more successful than him, although he lived in a basically one-room house with his six children and wife in Buckingham County in Virginia. Why was he more successful? Jefferson said, “Because he’s so happy.”

 

Do you know who else is feeling both happy and successful? People who owned an east-end home prior to the COVID pandemic. In two or three years, their real estate value increased substantially. Some folk’s home values went up a few hundred thousand dollars while others went up a few million dollars. Truly amazing. Of course, they really can’t go out and spend the money unless they sell the house, but it’s nice to know something they invested in has gone up very nicely in value.

 

Just this week a good friend went sailing with me. He explained that his best investment was buying his first home, actually a trailer in Montauk, then trading to a small home in the Springs, to now owning a nice million-dollar-plus home in Southampton. He admitted if he had just kept renting, he would be in actual bad financial shape, especially in this inflationary economy. I suppose everyone who has owned real estate understands all of this.

 

Thirteen years ago, I was living in Montauk and dating the woman who is now my wife. We were dining at The Harbor Inn, which was actually very close to the Montauk Train Station. I believe I was there that night doing a restaurant review for the now-defunct Montauk Pioneer. After dinner, we joined East Hampton Police Chief Eddie Eckert and his wife for a drink. The “Chief” enjoyed an article I did about his mother being Grand Marshall for the Friends of Erin parade that year and suggested my wife and I have a drink with him and his wife. As our drinks were being prepared, a young 19-year-old walked into the bar section of the restaurant and declared, “Drinks for everyone at the bar on me!” 

 

It seemed he was celebrating a successful commercial fishing trip that had him at sea for a few days. He sat with us and explained that he was only 19 years old and owned his own commercial fishing boat, a house and also had a wife and kid. “I’ve done it all on my own!” he proudly said specifically to my wife and me. 

 

What he said next made me laugh, “You know everyone says buy a house, so I did. I paid cash. Boom I owned a house. But no one ever told me after you buy the house, all these expenses begin. Taxes, the electric bill, cable-TV bill, insurance, a gardener, repair men, the oil bill.” He laughed, then he said, “Now I work to support my house.” 

 

Thirteen years later, I wonder how he feels about buying that house in Montauk—perhaps a million dollars or two wiser.

 

My truest success happened when I decided to put two feet into a few hours’ old relationship. The woman who is now my wife asked me point blank only an hour or so after we first met if I was willing to put my “two feet into a relationship?” I said, “Why not?” Easily the best decision I have ever made and probably the best answer to a question I have ever given.

 

At the time, I had a dog, and her apartment complex prohibited dogs from being in rented apartments. So, then Cindi, not yet my wife bought a nice home, so no one could complain about my dog! The dog has since passed on, but the home has substantially increased in value. My wife loves to sit on her porch and write columns and play reviews. When she is on the porch, she is happiest. Like the day she looked up and a hummingbird was watching her write or two male deer eating the sunflower plants. That time she wasn’t so happy. Occasionally she calls out for me to come out to the porch and see the moon or an amazing sky of stars. I love to watch her cuddled up in the rocking chair I assembled, writing, reading, or doing research on the porch. 

 

Like I said, success comes in many forms, but it feels special.

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Where coastal elegance meets high fashion. East Hampton continues to attract some of the world's most coveted brands, transforming its charming streets into a summer destination for luxury shopping. From Chanel, Prada, and Louis Vuitton to Brunello Cucinelli, Loro Piana, Loewe, and Ralph Lauren, Main Street and Newtown Lane are lined with iconic fashion houses that blend coastal charm with world-class style.

East Hampton Luxury Shopping Guide

Where coastal elegance meets high fashion. East Hampton continues to attract some of the world’s most coveted brands, transforming its charming streets into a summer destination for luxury shopping. From Chanel, Prada, and Louis Vuitton to Brunello Cucinelli, Loro Piana, Loewe, and Ralph Lauren, Main Street and Newtown Lane are lined with iconic fashion houses that blend coastal charm with world-class style.

Read more
Wyndham Clark won his second U.S. Open this past Sunday at the historic Shinnecock Hills Golf Club in Southampton. Hundreds of spectators filled the grandstands at the 18th hole, while more lined the area between the ropes and the stands, eagerly watching history being made.

Wyndham Clark Wins Second U.S. Open Title at Shinnecock Hills

Wyndham Clark won his second U.S. Open this past Sunday at the historic Shinnecock Hills Golf Club in Southampton. Hundreds of spectators filled the grandstands at the 18th hole, while more lined the area between the ropes and the stands, eagerly watching history being made.

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Over the past week, there were 18 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 19 Listings that went into contract.

Which is a year over year DECREASE of 5%.

Hamptons Real Estate Market Data – Week of 6/​16/2026

Over the past week, there were 18 Listings that went into contract from Westhampton to Montauk.

Compared to this same week last year (2025), there were 19 Listings that went into contract.

Which is a year over year DECREASE of 5%.

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