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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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LOCAL EVENTS

Events

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Lina Maxine at Stephen Talkhouse

May 27 @ 08:00 PM - May 27 @ 10:00 PM
Stephen Talkhouse, 161 Main St, Amagansett, NY 11930
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28
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28
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Focaccia Garden Art

May 28 @ 11:00 AM - May 28 @ 12:30 PM
Chabad of the Hamptons 13 Woods Ln
28
May
28
May
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28
May

Upon This Ground: An Artist Talk with Joshua Obawole Allen and Jasmine Webster presented by BHM and Ma’s House

May 28 @ 05:00 PM - May 28 @ 06:00 PM
2539 Montauk Highway, Bridgehampton, NY 11932
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May
28
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28
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American Ballet Theatre Spring Gala

May 28 @ 06:30 PM - May 28 @ 10:00 PM
Cipriani South Street
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May
29
May
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29
May

SAG HARBOR IN FOCUS – Photography Exhibiton: Opening Reception, Fashion Show, and Award Ceremony

May 29 @ 05:00 PM - May 29 @ 07:00 PM
The Church, 48 Madison St, Sag Harbor, NY 11963
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6th Annual Battle of the Fantasy Girl Bands at the Talkhouse

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

  • NAMIRO made its Southampton debut in style on May 17 with a ribbon-cutting ceremony and VIP cocktail preview, joined by Mayor Manger. Guests enjoyed signature bites and high-energy vibes at this invite-only event.⁠
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Conceptualized by music and hospitality heavyweights, NAMIRO Sushi is more than a restaurant—it’s where sleek design, elevated Asian cuisine, and nightly celebration collide. Located at 76C Jobs Lane in Southampton, NAMIRO opened its doors to the public on May 21 and is open seven days a week, year-round.⁠
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📸: Rob Rich/SocietyAllure.com ©2025 ⁠
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Check out the gallery at Hamptons.com (Link in Bio)⁠
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#namirosushi #hamptons #southampton ⁠
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  • It’s Memorial Day Weekend in The Hamptons! 

So many pop-ups, collaborations, and more! 

🎶 Chloe Caillet & Kaytranada at The Surf Lodge
📍 183 Edgemere St, Montauk, NY
📅 Saturday, May 24 | 🕓 Doors at 4PM

🔥 SlowFires NYC x Ruschmeyers Pizza Pop-Up
📍 Ruschmeyers, 161 2nd House Rd, Montauk, NY
📅 Fri, May 23 – Sat, May 24 | 🕓 4–9PM

🎨 Dolce Vita Pop-Up in Southampton
📍 95 Main Street, Southampton, NY
📅 Fri, May 23 – Sun, May 25 | 🕚 11AM–3PM
Dolce Vita x Down the Street’s Summer Art Series: view new art drops, shop, and enjoy seasonal treats.

👜 Lands’ End x Round Swamp Farm
📍 Round Swamp MTK – 71 S Elmwood Ave, Montauk
📍 Round Swamp BH – 97 School Street, Bridgehampton, NY
📅 Fri, May 23 – Sat, May 24 | 🕣 8:30AM–6PM
Get a custom tote with any $200+ purchase—1 per customer.
📸 AD: Ryan Woehler | 📷: Chris Klinge | 👗: Jenny Huebner | 📸 Asst: Dan Kleinschmidt

🎤 Hello Brooklyn at The Stephen Talkhouse
📍 161 Main St, Amagansett, NY
📅 Saturday, May 24 | 🕥 10:30PM
It’s not a true Hamptons weekend without a night at Talkhouse! Dance the night away with Hello Brooklyn.

🍪 Levain Bakery X John’s Drive-In
📍 Levain Bakery, 354 Montauk Hwy, Wainscott, NY
📅 Starts May 23 | 🕗 8AM–5PM
Thick, gooey Levain cookies + classic scoops from John’s = summer magic.

🪩 Silent Disco Dance Party at Guild Hall
📍 158 Main St, East Hampton, NY
📅 Sunday, May 25 | 🕗 8–11PM
Dance in the garden!

🪁 Kites for Kids Benefit at Main Beach
📍 101 Ocean Ave, East Hampton, NY
📅 Saturday, May 24 | 🕑 2–5PM
Decorate & fly a kite—all proceeds benefit the Eleanor Whitmore Early Childhood Center.
📸 Photo Credit: John Musnicki

🍻 Jon Divello at Kidd Squid
📍 11 Spring St, Sag Harbor, NY
📅 Sunday, May 25 | 🕔 5–7PM
Live music + fresh brews = perfect weekend vibes.

🌸 Garden Club of East Hampton’s Garden Party
📍 Mulford Farm, 10 James Lane, East Hampton, NY
📅 Friday, May 23 | 🕕 6–8PM
Enjoy hors d’oeuvres, drinks, and a Silent Auction featuring art, books, and more.

🌿 Jenni Kayne’s Hamptons Kickoff
Celebrate summer with in-store events all weekend long at the Amagansett Store and the Southampton Store!
📸 Photo Credit: Holly Sarah Burgess

Tap the link in bio for info!
  • My curiosity piqued when I saw the new, shovel-ready plans at 28 Pepperidge Lane in Amagansett. Included with this nearly two-acre property, are sophisticated and luxurious plans by the firm Resolution: 4 Architecture (RES4). New construction in the Hamptons isn’t easy—but what if your dream home could be architect-designed and delivered directly to you? What is the latest in prefab architecture in 2025?⁠
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To explore this intriguing approach further, Scott connected me directly with Robert Luntz, the co-founder of RES4. See our conversation on redefining luxury through modern modular design, its growing relevance in the Hamptons, and the future of high-end prefabrication.⁠
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For more information about the plans in place at 28 Pepperidge Lane, Amagansett, contact Scott Bradley.⁠
⁠
RES4 has been a pioneer in modern prefab architecture. What inspired you to focus on this method of construction?⁠
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We’ve spent over two decades innovating ways to deliver exceptional, modern homes efficiently and affordably. Our modular methodology uniquely allows us to combine luxury, precision, and accessibility, transforming the landscape of high-end housing by delivering refined design to a broader market.⁠
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@resolution4architecture @hamptons_waterman_lifestyle @hamptonsrealestate⁠
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Read the full interview at Hamptons.com. (Link in Bio)⁠
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#architecture #hamptons #hamptonsrealestate #luxury⁠
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  • NYC Second Chance Rescue hosted its 5th Annual Rescue Ball Gala — a dazzling evening of compassion, community, and celebration — at Pier Sixty in New York City.⁠
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The event honored two inspiring individuals for their outstanding advocacy and dedication to animal welfare: Martha Stewart, iconic lifestyle entrepreneur and lifelong animal champion, and Dr. Dan Belkin, leading dermatologist and passionate rescue animal advocate.⁠
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Set against the stunning waterfront views of Pier Sixty, the gala brought together philanthropists, celebrities and compassionate supporters to champion NYC Second Chance Rescue’s mission. The night featured a special live performance by Rob Thomas, a special appearance by Georgina Bloomberg, a lively auction led by celebrity host Elvis Duran, host of Elvis Duran and the Morning Show on Z100, surprise guest Alexandra Daddario, and a high-energy DJ set by GEO ROC that kept guests dancing for a cause.⁠
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📸: Sylvain Gaboury/PMC⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#secondchancerescue #nyc #marthastewart #robthomas ⁠
  • The 14th Annual Montauk Music Festival is back! ⁠
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Check out the top Hamptons events this weekend!⁠
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🎶 Montauk Music Festival⁠
📅 Fri, May 16 – Sun, May 18⁠
📍 Multiple venues, Montauk, NY⁠
A volunteer-run, grassroots celebration of Montauk’s vibrant live music scene.⁠
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🐾 ARF’s Pet Celebration Day⁠
📅 Sat, May 17 | 📍 124 Daniel Hole Rd, East Hampton⁠
A tail-wagging good time! ⁠
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🧵 Airing of the Quilts⁠
📅 Sat, May 17 | 12–5PM⁠
📍 The Art Center at Duck Creek, East Hampton⁠
A beloved outdoor tradition! Bring a quilt, share your story, and explore the beauty of the log cabin pattern.⁠
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🌴 Jimmy Buffett Day at Clubhouse Hamptons⁠
📅 Sat, May 17 | 1–5PM⁠
📍 174 Daniels Hole Rd, East Hampton⁠
Tropical attire encouraged! Live music, raffles, and good vibes—all for a great cause.⁠
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🎉 Hampton Library’s Family Fest Fundraiser⁠
📅 Sat, May 17 | 2–5PM⁠
📍 Channing Daughters Winery, Bridgehampton⁠
Games, music, food trucks, and “The Sled” mobile tech library—family fun with a local flair!⁠
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🎸 Jackie Greene at The Stephen Talkhouse⁠
📅 Fri, May 16 | 7PM⁠
📍 161 Main St, Amagansett⁠
Roots rocker Jackie Greene takes the stage. Don’t miss this intimate performance!⁠
⁠
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🚲 Springs Bike Ride⁠
📅 Sat, May 17 | 10AM–12PM⁠
📍 Start: Bridge Lane over Sag Pond⁠
Ride through historic Springs after a quick tour of the local library and historical society.⁠
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😂 Comedy in The Hamptons: Joe DeVito⁠
📅 Sat, May 17 | 7–10:30PM⁠
📍 Canoe Place Inn, Hampton Bays⁠
Catch NYC comedy favorite Joe DeVito for a night of nonstop laughs.⁠
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💿 Hamptons Vinyl Record Fair⁠
📅 Sun, May 18 | 12–6PM⁠
📍 LTV Studios, Wainscott⁠
Dig through crates, catch live sets, and vibe with fellow music lovers.⁠
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🎬 Now Playing at Sunset Theater: Sinners⁠
📅 Fri, May 16 – Mon, May 19⁠
📍 2 Brook Rd, Westhampton Beach⁠
A chilling new horror film starring Michael B. Jordan and Hailee Steinfeld.⁠
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📷 Anthony Lombardo Photography Exhibition⁠
📅 Sat, May 17 | 12–4PM⁠
📍 Southampton Cultural Center⁠
A showcase of stunning visuals from a standout local photographer.⁠
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📲 Head to Hamptons.com for more events!⁠
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#hamptonsweekend #montaukmusicfestival #weekend⁠
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  • On Tuesday, April 29th, Kenneth Cole and co-hosts led a special launch event at the Core Club in New York City in partnership with the Mental Health Coalition ahead of Mental Health Awareness Month.⁠
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The evening began with an intimate reception, allowing guests to mingle and connect over cocktails. It was followed by an elegant seated dinner and a special performance from multi-platinum recording artist Rachel Platten.⁠
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Check out the full gallery at Hamptons.com (Link In Bio)⁠
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📸: Photography Courtesy of BFA: Yvonne Tnt⁠
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#kennethcole #rachelplatten #rachelrosnahan #nyc
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