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February 26, 2023

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

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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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Film and Television Line Producer and Springs resident Jonathan Shoemaker brings his talents to the East End with his theater company, The Accabonac Theater Project. Its inaugural production, This Land Is Your Land, will run January 30 through January 31 at 7pm with a 5pm show on February 1 at Hoie Hall at St. Luke’s Episcopal Church in East Hampton. The production features a trio of short plays titled “General Store,” “Baker Sale,” and “Mystery Art.”

INTERVIEW: Jonathan Shoemaker on the Accabonac Theater Project, This Land Is Your Land, and Life in Springs

Film and Television Line Producer and Springs resident Jonathan Shoemaker brings his talents to the East End with his theater company, The Accabonac Theater Project. Its inaugural production, This Land Is Your Land, will run January 30 through January 31 at 7pm with a 5pm show on February 1 at Hoie Hall at St. Luke’s Episcopal Church in East Hampton. The production features a trio of short plays titled “General Store,” “Baker Sale,” and “Mystery Art.”

Read more
When Jesse Bongiovi launched Hampton Water Wine Co. with his dad, Jon Bon Jovi, in 2018, he helped redefine what modern rosé could look and feel like—sun-soaked, effortless, and rooted in moments shared with the people you love.

Now, with the growth of Lily Pond Group, he’s expanding that vision far beyond the bottle. Influenced by years spent in the Hamptons’ uniquely relaxed and refined culture, Jesse’s approach to brand-building is all about capturing a feeling: the blend of ease, taste, and connection that defines a perfect summer day out East.

From Rosé to a Lifestyle Collective: Jesse Bongiovi on Building Lily Pond Group

When Jesse Bongiovi launched Hampton Water Wine Co. with his dad, Jon Bon Jovi, in 2018, he helped redefine what modern rosé could look and feel like—sun-soaked, effortless, and rooted in moments shared with the people you love.

Now, with the growth of Lily Pond Group, he’s expanding that vision far beyond the bottle. Influenced by years spent in the Hamptons’ uniquely relaxed and refined culture, Jesse’s approach to brand-building is all about capturing a feeling: the blend of ease, taste, and connection that defines a perfect summer day out East.

Read more
Amber Waves Farm has become one of the East End’s most beloved gathering places—a thriving mix of working farmland, educational resources, community space, and local food destination rooted in purpose. The farm and market are located at 367 Main Street, Amagansett and open daily.

Cultivating Connection on the East End: A Conversation with the Founders of Amber Waves Farm

Amber Waves Farm has become one of the East End’s most beloved gathering places—a thriving mix of working farmland, educational resources, community space, and local food destination rooted in purpose. The farm and market are located at 367 Main Street, Amagansett and open daily.

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  • 2026 Long Island Restaurant Week: Spring Edition, celebrating its 15th year, will start on Sunday, April 26th, and end on Sunday, May 3rd. ⁠
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Enjoy delicious 3-course meals at your favorite restaurants in the Hamptons. 
⁠
Check out menus and more at Hamptons.com (Link in Bio)⁠
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#longislandrestaurantweek #hamptons #dining #easthampton #restaurant
  • ✨ Top Hamptons Events This Weekend ✨⁠
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From mystery-filled evenings to art, music, and outdoor adventures—here’s what’s on deck this weekend:⁠
⁠
🔍 The Fourth Annual Hamptons Whodunit⁠
📅 Thurs, April 16 – Sun, April 19⁠
📍 East Hampton⁠
A four-day true crime and mystery festival featuring panels, book signings, publisher teas, and themed dinner events.⁠
⁠
🎹 Nana Miyoshi at The Church⁠
📅 Friday, April 17 | 6–7:30 PM⁠
📍 Sag Harbor⁠
An elegant evening of piano featuring Bach, Beethoven, Chopin, and more.⁠
⁠
🏃‍♀️ Katy’s Courage 5K Run/Walk⁠
📅 Saturday, April 18 | 8:30 AM–12 PM⁠
📍 Sag Harbor⁠
A scenic run (or walk) for a meaningful cause, now in its 14th year.⁠
⁠
🎨 14th Annual ArtGroove⁠
📅 April 18–19 | Opening Sat 6–10 PM⁠
📍 East Hampton⁠
Contemporary art, live music, video installations, and a dance party—featuring works by 18 artists and performances throughout the night.⁠
⁠
🌎 Earth Day Swap Party at CMEE⁠
📅 Saturday, April 18 | 10 AM–1 PM⁠
📍 Bridgehampton⁠
Celebrate Earth Day with a community swap—bring books, puzzles, or sports gear and take home something new.⁠
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🖼️ Upside Down Zebra Guided Tour⁠
📅 Saturday, April 18 | 12 PM⁠
📍 Water Mill⁠
A fascinating exhibition blending children’s art archives with contemporary works.⁠
⁠
🦅 Birds of Prey at SOFO⁠
📅 Saturday, April 18 | 12–1 PM⁠
📍 Bridgehampton⁠
Meet rescued birds up close with the Wildlife Rescue Center team.⁠
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🥾 Whiskey Hill 40th Anniversary Hike⁠
📅 Saturday, April 18 | 10–11 AM⁠
📍 Bridgehampton⁠
Explore local history on this guided nature walk.⁠
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🎶 Live Music at The Sunset Social Club⁠
📅 April 17–19 | 6 PM⁠
📍 Westhampton Beach⁠
Cocktails, cinema, and live music at one of the Hamptons’ chicest theaters.⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #weekend #hamptonswhodunit #easthampton
  • Top Hamptons Events This Weekend ☀️⁠
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🎨 The Fifth Annual Creativity Conference⁠
🗓 Saturday, April 11 | 9:30am–6pm⁠
📍 The Church, Sag Harbor⁠
A rare chance to engage with inspiring thinkers and creators, curated by April Gornik.⁠
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🛍 Keep it Local 2026⁠
🗓 Saturday, April 11 | 10am–9pm⁠
📍 Sag Harbor Village⁠
A village-wide celebration with special experiences, local offerings & community vibes.⁠
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🧘‍♀️ Morning of Mindfulness & Stillness⁠
🗓 Saturday, April 11 | 11am–12pm⁠
📍 Dragon Hemp Apothecary, Sag Harbor⁠
Reset with a calming session led by Reiki Master Marissa Kerwin.⁠
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🥾 Town & Country Hike⁠
🗓 Saturday, April 11 | 10am–12:30pm⁠
📍 Amagansett Free Library⁠
A scenic hike through Main Street, woodlands & farm fields.⁠
⁠
🎭 Our Fabulous Variety Show – Staged Reading⁠
🗓 Saturday, April 11 | 6–6:30pm⁠
📍 The Studio on Main, East Hampton⁠
Short plays by local and NYC playwrights.⁠
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🍝 Rotary Club Spaghetti Dinner⁠
🗓 Sunday, April 12 | 12–9pm⁠
📍 Villa Paul, Hampton Bays⁠
A community favorite supporting scholarships & local programs.⁠
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🎷 East End Jazz: Miles & Coltrane Tribute⁠
🗓 Sunday, April 12 | 2–5pm⁠
📍 Southampton Cultural Center⁠
Live jazz + community jam honoring two legends.⁠
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🎬 Sag Harbor Cinema: The Drama⁠
🗓 April 11–13⁠
📍 Sag Harbor Cinema⁠
A wedding-week story starring Zendaya & Robert Pattinson.⁠
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🍷 Cooking Class with Chef Alex⁠
🗓 Sunday, April 12 | 3:30–6:30pm⁠
📍 R.AIRE at The Hampton Maid⁠
Hands-on tapas & paella with wine pairing.⁠
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Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #weekend #sagharbor #cooking #easthampton
  • Let’s be honest—there are two types of people in the Hamptons: those who go to Goldberg’s, and those who are wrong. By 8:30 a.m., the line is already forming, a mix of locals, contractors, summer people, and at least one guy pretending he doesn’t eat carbs while ordering a scooped bagel the size of a small planet.

Read the full review at Hamptons.com

@theoriginalgoldbergs 

#goldbergs #bagel #hamptons
  • Perched 162 feet above sea level on one of Shelter Island’s highest natural elevations, the modern residence at 42 Prospect Avenue + Part 23 Serpentine Drive, known as “Treetops,” is recognized for both its architecture and its wide-ranging views. Built in 2002 and designed by architect Frederick Stelle, who was honored with an AIA Archi Award, the home was inspired by the original structure on this site that was designed by Peter Schladermundt—whose work was featured at the 1964 New York World’s Fair.⁠
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Set on 3.41 acres, the three-story residence overlooks Peconic Bay, the North Fork, Long Island Sound, and, on clear days, has views to the Connecticut shoreline. The design uses expanses of glass to open the house to its surroundings, keeping the landscape in constant view.⁠
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Owned by financier Lewis Ranieri, widely recognized for his role in developing the mortgage-backed securities market, the property serves as a counterpoint to the pace of his professional life.⁠
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@penelopemoorerealestate⁠
@hamptonsrealestate⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#shelterisland #treetops #awardwinningmodernhome #luxuryrealestate
  • Empire of the Atlantic is a breathtaking taste of what everyone loves about the magic of the waters off the East End, specifically Montauk. Jeff Ragovin, Founder and CEO of Ragovin Ventures, is the executive producer through Bounty Uncharted Productions and assembled a team to bring the project to fruition.⁠
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This 15-minute documentary (available on YouTube) is currently one of the hottest East End must-sees. Being able to watch the various whales, giant bluefin tuna, marlins, hammerhead sharks, and so many other fish feeding off Montauk in phenomenal drone-captured color footage is spellbinding.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#empireoftheatlantic #montauk #ocean #documentary
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