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Hamptons.com
August 7, 2025

Laura Dalessandro on Hamptons Real Estate, Leadership, and Life West of the Canal

David Andrewsby David Andrews
in Real Estate, Trending
Home Real Estate
Laura Dalessandro on Hamptons Real Estate, Leadership, and Life West of the Canal

In the world of Hamptons real estate, few names carry the weight and warmth of Laura Dalessandro. A powerhouse broker and trusted leader, Laura brings over two decades of experience to the table, along with a deep local knowledge that only a lifelong Long Islander can offer. 

 

Specializing in luxury waterfront properties, she has built her reputation on Dune Road, but her reach spans the entire Hamptons, from Westhampton Beach to Montauk. To say she is a top-producing agent is true, but is incomplete: Laura Dalessandro is a community builder and mentor. And yes, she does have a million-dollar smile!

 

At the helm of the Laura Dalessandro Team at Saunders & Associates, Laura combines unmatched market insight with a hands-on approach that makes every client feel like her only client. Her background as the former Village Clerk for West Hampton Dunes—spanning 14 years—gives her a rare perspective on coastal regulations, property potential, and the rhythms of life by the sea. 

 

Laura’s reputation and results are driven by a simple principle: relationships matter. So do the details. Whether you’re looking for a summer getaway or a forever home, she brings the same level of passion and precision to every deal. We sat down with Laura to talk about what inspires her, how she leads her team, and why waterfront living in the Hamptons is truly one-of-a-kind.

 

Your background includes 14 years as Village Clerk of West Hampton Dunes. How has that civic experience influenced your approach as a broker?

 

That experience gave me a front-row seat to the inner workings of coastal governance, zoning, and environmental policy—knowledge that most brokers simply don’t have. I’ve worked closely with engineers, attorneys, the Army Corps of Engineers, and homeowners on issues ranging from dune restoration to FEMA compliance. So when my clients come to me with questions about setbacks, flood insurance, or building approvals, I’m able to provide insight that’s grounded in real-world experience.

 

More than that, my time as Village Clerk instilled in me a deep sense of accountability. I don’t take shortcuts. I do the work, I know the rules, and I advocate fiercely for my clients’ best interests.

 

You’ve built a reputation as a Dune Road expert—what makes this stretch of coastline so special, and what should buyers know about owning waterfront property here?

 

Dune Road is unlike any other place. It offers a rare blend of raw natural beauty, privacy, and proximity to the water that draws people back year after year. What makes it truly special is the lifestyle—it’s not just about owning a home, it’s about waking up to panoramic ocean views, paddleboarding at sunrise, and hosting loved ones and friends with the beach as your backyard.

 

That said, owning waterfront property here also comes with unique responsibilities. From understanding flood zones and elevation certificates to navigating building regulations and environmental protections, experience matters. That’s where I come in. After decades of working on Dune Road and even serving as the Village Clerk of West Hampton Dunes, I help my clients anticipate the nuances and feel confident in their investment.

 

With over 20 years of experience in the Hamptons market, how have you seen the region evolve, and what stays timeless about life out here?

 

The Hamptons have evolved dramatically over the last two decades. We’ve seen the rise of luxury enclaves, year-round residents replacing seasonal ones, and a major shift in buyer expectations—especially after the pandemic. Technology and design preferences have changed, too—people want open floor plans, work-from-home setups, wellness spaces, and seamless indoor-outdoor living.

 

But what remains timeless is the essence of life out here: the connection to nature, the sense of escape, and the tight-knit community that makes even a second home feel like a true home. Whether someone is here for the summer or all year long, the Hamptons still offer that breath of fresh air and grounding presence people crave.

 

You lead your own team at Saunders & Associates. What does leadership mean to you in the context of real estate, and how do you foster mentorship within your group?

 

To me, leadership in real estate means creating a culture where everyone feels empowered, supported, and driven to be their best. I lead by example—with transparency, integrity, and a strong work ethic—but I also believe in lifting others up. I don’t see mentorship as a one-time conversation; it’s a daily commitment. Whether it’s teaching negotiation strategies, helping a junior agent through a tough deal, or celebrating a small win, I want my team to know they’re never alone in this business.

 

What I’ve learned is that when you invest in your team, you build a better business and better relationships, which translates directly to how we serve our clients.

 

What’s your strategy for staging and positioning high-end homes to stand out in the competitive Hamptons marketplace?

 

High-end homes demand a curated approach. I begin by understanding the story each property tells—its architecture, setting, and lifestyle value. From there, I work with top-tier stagers, photographers, and videographers to create a cohesive visual narrative that captures that story. When we show a home, we’re showing a dream.

 

Strategic pricing, compelling marketing copy, and precision-targeted digital campaigns are also essential. I leverage my deep local network and global platforms to maximize visibility. Every detail matters. Right down to the scent in the home during a showing. In this market, luxury is about experience, and my job is to make sure that experience starts the moment a buyer clicks on the listing.

 

You’ve worked with clients from all over—from buyers new to the Hamptons to longtime locals. How do you tailor your approach to meet such diverse needs?

 

Every client has a unique story, and I take the time to listen. A first-time buyer may need education and reassurance, while a seasoned investor wants sharp data and speed. Locals might be navigating emotional sales of generational homes, and out-of-towners often need community insights, contractor referrals, and ongoing support long after the sale.

 

I customize my approach based on what each client values most—whether it’s privacy, investment return, or building their dream home. Real estate is never one-size-fits-all, and I pride myself on being both a trusted advisor and a strategic problem-solver at every step.

 

What does “success” look like to you in this business, and what continues to drive your passion for the work after so many years?

 

Success, for me, isn’t just about the numbers—it’s about impact. It’s about earning trust, building long-term relationships, and helping clients make life-changing decisions with confidence and clarity. I measure success in the number of referrals I get, the thank-you notes I receive, and the sense of pride I feel knowing I’ve made a difference.

 

What drives me after all these years is the combination of challenge and purpose. No two days are the same, and no two clients are either. I love the problem-solving, the pace, the relationships. Most of all, I love helping people find their place in this special part of the world.

 

To learn more about Laura Dalessandro, click here.

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November 7 @ 02:30 PM - November 7 @ 03:30 PM
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Sabrina Rudin x Mill's Dinner in the Garden

  • A few minutes past Amagansett Village, in that quiet pocket between the ocean and the bay, the new estate built by Bluefin, 137 Cross Highway to Devon, has intrigued me since the moment I saw it — a rare combination of proximity to the Village, craftsmanship, and design integrity in one of the most desirable areas on the East End. ⁠
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Real-savvy Hamptons people know that Amagansett North is a quiet kind of magic—close enough to feel the Village’s heartbeat, far enough to hear the birds. If you think 137 Cross Highway to Devon is out of the way, then you don’t know Amagansett.⁠
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Four minutes to Amber Waves, under five to Balsam Farms and the Village, and less than ten to the ocean at Atlantic Avenue Beach.⁠
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Location, of course, is the headline anyway. The essentials—farm stands, ocean and bay beaches, golf and racquet clubs, coffee, restaurants, provisions—are so close they become afterthoughts: grab greens at Balsam, seafood at Stuarts, swing back for a baguette at Amber Waves, be home before the ice melts. It’s the rare setup where everyday errands feel like part of the vacation.⁠
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@romainehamptons @sarahminardire⁠
@hamptonsrealestate⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptonsrealestate #hamptons #amagansett
  • @paddlediva and @wychs_bloom inaugural Witches Paddle on Wednesday, October 29 at Paddle Diva was a huge success. 

A portion of the proceeds benefited the Surfrider Foundation’s Eastern Long Island Chapter. @surfridereasternlongisland 

#witches  #witchespaddle #halloween #paddleboarding #hamptons
  • Little Lucy’s 24th Annual Halloween Pet Parade pumpkin👻

#halloween #halloweencostume #petcostume #halloweenpetcostume #hamptons
  • Saunders & Associates announced the kickoff of its 12th Annual Thanksgiving Donation Drive, renewing a cherished Hamptons tradition that supports local food banks from Westhampton to Montauk. This year, the firm has set an ambitious goal: $50,000 in monetary donations to be distributed directly to community partners serving year-round families across the East End.⁠
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All donations made to the GoFundMe will be matched dollar for dollar by Andrew & Colleen Saunders. Every dollar contributed will go entirely to food pantries in the Hamptons, where the need remains critical.⁠
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Last year’s drive surpassed its monetary goal, powered by more than 100 contributions from Saunders agents and the wider Hamptons community. Those funds helped ensure local families had access to essential resources during the holiday season—a critical time of year for many.⁠
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In the years since COVID-19, Saunders & Associates has shifted to monetary contributions, enabling local pantries to purchase essentials in bulk that their clients need most. Continuing a commitment from last year, Colleen and Andrew Saunders will personally match every dollar donated, effectively doubling the impact of each gift.⁠
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“Year twelve is a major milestone, and a mirror on the Hamptons community at its best,” said Steve Glick, Senior Vice President of Marketing at Saunders & Associates. “It reflects the generosity of a community that shows up for one another beyond the summer season. When you give to this drive, you help neighbors directly and immediately. Every contribution is multiplied, and every dollar goes where it’s needed most.”⁠
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Saunders & Associates’ agents and staff—who live and work in the Hamptons year-round—will once again champion the effort, rallying clients, friends, and local businesses to participate throughout the Thanksgiving season.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #hamptonsrealestate #localfoodpantries #community⁠
  • Happy Halloween! Get ready for a spooky time at some of the best Halloween parties in the Hamptons! 

Check out the top Hamptons events this weekend!

👻 Calissa’s Halloween in the Hamptons Party
🕔 Fri, Oct 31 | 5PM – 2AM
📍 Calissa Hamptons, Water Mill
Wear your costume to dinner & toast with a complimentary glass of bubbles! 💃🥂
🔗 Link in Bio

🎸 Halloween Party with Hello Brooklyn
🕙 Fri, Oct 31 | 10PM
📍 The Stephen Talkhouse, Amagansett
Party at the most iconic music venue in the Hamptons! 🎶
🔗 Link in Bio

🎬 Hollywood Halloween Costume Party
🕖 Sat, Nov 1 | 7PM – Midnight
📍 Sunset Theater, Westhampton Beach
Dress up as your fave movie character 🎭 — 2 free cocktails & prizes! 🍸🏆
🔗 Link in Bio

🎧 Clubhouse Hamptons’ Halloween Party
🕘 Fri, Oct 31 | 9PM
📍 Clubhouse Hamptons, East Hampton
Costume contest & beats by DJ Chile, CK Beats & Nick Corredor 🔥
🔗 Link in Bio

💿 Disco Ball at LTV Studios
🕕 Sat, Nov 1 | 6PM – 9PM
📍 LTV Studios, Wainscott
A retro-inspired evening of music, dancing, food, & raffles! 🕺✨
🔗 Link in Bio

🍽️ Long Island Restaurant Week: Fall Edition
🗓️ Nov 2 – 9 | 12PM – 12AM
📍 Various Locations
Dine at new favorites & support local restaurants! 😋
🔗 Link in Bio

🎺 East Meets West Jazz Jam Session
🕑 Sun, Nov 2 | 2PM – 5PM
📍 Southampton Cultural Center
REEB kicks off a live jazz jam — all musicians welcome to join! 🎷
🔗 Link in Bio

🎈 Halloween Party for Kids
🕞 Fri, Oct 31 | 3:30PM – 5:30PM
📍 Glover’s Park, Westhampton Beach
DJ, dancing, candy & surprises for the little ones! 🍬🎃
🔗 Link in Bio

🎨 Almond Artists & Writers Series: Fitzhugh Karol
🕕 Mon, Nov 3 | 6PM
📍 Almond, Bridgehampton
Art meets dining — enjoy a 3-course family-style meal with artist Fitzhugh Karol. 🍷🎭
🔗 Link in Bio

🌕 Full Frost Super Moon Hike
🕔 Wed, Nov 5 | 5PM – 6PM
📍 SOFO, Bridgehampton
Hike under the moonlight, sip cider & relax with gong vibrations. 🌙🍎
🔗 Link in Bio

🧘‍♀️ Bodymind Ballwork Workshop
🕑 Sat, Nov 1 | 2PM – 5PM
📍 One Ocean Yoga, Bridgehampton
Relieve tension & rejuvenate with this bodywork session using rubber balls. 🧘‍♀️✨
🔗 Link in Bio

#halloween #hamptons #artists #art #hollywood #costume
  • Dust off your favorite witch’s hat and opt for a paddleboard instead of a broom for Paddle Diva & Wych’s Bloom’s inaugural Witches Paddle on Wednesday, October 29, from 4–6 p.m. at Paddle Diva (10 Boat Yard Rd., East Hampton, NY). A portion of the proceeds will go to the Surfrider Foundation’s Eastern Long Island Chapter and its efforts to protect the world’s oceans, waves, and beaches through dedicated activism. ⁠
⁠
We’ve all seen Witches Paddles grace our social media feeds, and now you can partake in the spooky fun! This tradition combines Halloween vibes with the healing power of nature as you glide and take in the beautiful Three Mile Harbor views.⁠
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Gina Bradley excitedly shared, “I am thrilled to be hosting this at Paddle Diva’s permanent location inside Swan’s Marina (formerly Vanderveer’s). This kind of paddle has been on my mind for many years, as I’ve seen them in all parts of the world, and it looks so cool seeing all the witches gracefully gliding along the water. This is particularly exciting because we’ve joined forces with Wych’s Bloom, a local herbal apothecary brand, and Surfrider to raise money and awareness for ocean and clean bay initiatives that are crucial for our waters on the East End of Long Island.”⁠
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“As an herbalist, Samhain, or Halloween, offers a special occasion for me to celebrate the healers who came before us to teach the wisdom of the plants in our region. I had seen people gathering for Witches Paddles all over the country, and as a surfer, I connected instantly with these events. When I texted Gina the idea, she was immediately in. That’s what I love about the women on the East End—they’re always up for an adventure,” shared Wych’s Bloom owner and Surfrider Foundation board member Christina Winters.⁠
⁠
Join us in taking part in this one-of-a-kind event! Craft a witch’s outfit and set sail at the inaugural Witches Paddle for a great cause.⁠
⁠
@paddlediva @wychs_bloom⁠
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#witch #witchespaddle #paddlediva #hamptons #halloween #easthampton⁠
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