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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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Hofstra Pro-Am Tennis & Pickleball Event in the Hamptons

August 29 @ 09:00 AM - August 29 @ 03:00 PM
Hampton Racquet - 172 Buckskill Rd, East Hampton, NY 11937
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The HUB Hosts Printemps’ First Hamptons Pop-Up Activation- Printemps × CocoRedoux Atelier 8/29-8/31

August 29 @ 11:00 AM - August 31 @ 06:00 PM
The HUB 2183 Montauk Hwy, Bridgehampton, NY 11932
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Jaws – 50th Anniversary

August 29 @ 01:30 PM - August 29 @ 10:00 PM
2 Brook Road, Westhampton Beach, NY 11978
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Gene Casey at The Clubhouse

August 29 @ 06:00 PM - August 29 @ 09:00 PM
174 Daniels Hole Road, East Hampton, NY, 11937
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Hamptons Jazz Fest Presents JANE IRA BLOOM QUARTET

August 29 @ 06:00 PM - August 29 @ 07:30 PM
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Sabrina Rudin x Mill’s Dinner in the Garden

Sabrina Rudin x Mill's Dinner in the Garden

  • Check out the Top Hamptons Events This Weekend!⁠
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📍 The Montauk General X Lands’ End⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 10am–3pm⁠
📌 Montauk General Store at The Brunch Playhouse, 14 Amagansett Square⁠
🎁 Free limited-edition tote with orders over $100 (while supplies last)⁠
⁠
🐎 50th Annual Hampton Classic Horse Show⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 8am–5pm⁠
📌 240 Snake Hollow Rd, Bridgehampton⁠
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🍇 Wölffer Estate Vineyard PPL All-Star 2025⁠
🗓 Sat, Aug 30⁠
📌 Wölffer Estate Vineyard, Sagaponack⁠
🎾 World-class padel at the Hamptons’ most iconic vineyard⁠
⁠
😂 Zarna Garg at WHBPAC⁠
🗓 Sun, Aug 31 | 8pm–9:30pm⁠
📌 76 Main St, Westhampton Beach⁠
⁠
🎶 Joe Delia & Friends at The Clubhouse Hamptons⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 174 Daniels Hole Rd, East Hampton⁠
⁠
🎧 Silent Disco Dance Party in the Garden⁠
🗓 Sun, Aug 31 | 8pm⁠
📌 Guild Hall, East Hampton⁠
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👗 Marfa & Friends Trunk Show⁠
🗓 Thurs, Aug 28 – Sat, Aug 30⁠
📌 Sag Harbor⁠
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🎬 Jaws’ 50th Anniversary Screening at Sunset Theater⁠
🗓 Fri, Aug 29 – Mon, Sept 1⁠
📌 Water Mill⁠
⁠
👠 Hamptons Fashion Week⁠
🗓 Sat, Aug 30 | 2pm⁠
📌 Location TBA⁠
⁠
🎸 Dogpark at The Stephen Talkhouse⁠
🗓 Sat, Aug 30 | 8pm⁠
📌 Amagansett⁠
⁠
🍴 Stirring The Pot: Florence Fabricant & Pete Wells⁠
🗓 Sun, Aug 31 | 11am–1pm⁠
📌 Guild Hall, East Hampton⁠
⁠
🌊 ANOTR at Surf Lodge⁠
🗓 Sun, Aug 31 | 4pm⁠
📌 Montauk⁠
⁠
🎷 Garden Concert ft. Freddy DeBoe⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 Canoe Place Inn, Hampton Bays⁠
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🔗 Link in Bio⁠
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#hamptons #wolffer #padel #landsend #montauk #fashion
  • Earlier this month, Shelter Island’s Rams Head Inn hosted a riveting Gilded Age Finale screening featuring lead actress Cynthia Nixon, award-winning costume designer Kasia Walicka Maimone, and executive producer/director Michael Engler.⁠
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📸:Rob Rich/SocietyAllure.com⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#ramsheadinn #gildedage #shelterisland #cynthianixon #shelterislandny
  • Culinary and lifestyle icon Ina Garten will host an intimate tea and garden tour at her famed East Hampton residence on Wednesday, August 27th from 4:00 – 6:00 p.m. A limited number of guests will be invited to share tea with Ina and walk with her through her celebrated gardens and grounds.⁠
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Known for her signature warmth and effortless approach to cooking and entertaining, Ina has earned a devoted following across generations. With her calm presence, foolproof recipes, and signature phrases like “store-bought is fine,” she takes the pressure off hosting, making room for only joy at the table.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #inagarten #community #easthampton
  • The magic of The Soho Sessions returns to the Hamptons this summer, bringing a rare and intimate live performance to Stephen Talkhouse in Amagansett on Monday, August 25, 2025. This one-night-only event features Grammy Award-winning artist Maren Morris (with introduction by the actor Jason Biggs) and the genre-defying powerhouse Yola in a night of music with purpose and soul.⁠
⁠
It’s also a night for change. The event supports Music Will, the largest nonprofit music education program for schools in the U.S., which aims to reach 10 million students annually by 2030. It’s a cause that hits home for Morris: “I loved my choir and theatre classes in high school; they really shaped my theory and love for being creative in every medium,” she recalls. “It also teaches you how to be a team player and work together.”⁠
⁠
Read the full article at Hamptons.com (Link in Bio)⁠
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#stephentalkhouse #talkhouse #amagansett #marenmorris #yola #concert #hamptons
  • @wagsandwalks @themontaukbeachhouse 

Puppies + Pilates + @montaukila = The Perfect Day

Check out our Events Calendar for more events! (link in bio)

#wagsandwalks #animaladoption #adoptdontshop❤️ #dog #montauk #montaukbeachhouse #montaukila #pilates
  • Check out the Top Hamptons Events This Weekend! ⁠
⁠
✨ 50th Annual Hampton Classic Horse Show⁠
📅 Sun, Aug 24 – Sun, Aug 31, 2025 | 8am–5pm⁠
📍 240 Snake Hollow Rd, Bridgehampton, NY⁠
🐴 One of the largest outdoor horse shows in the U.S., a premier summer destination for competitors & spectators.⁠
⁠
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🎶 Apollo in the Hamptons⁠
📅 Fri, Aug 22, 2025 | 6pm⁠
📍 Si Si, 295 Three Mile Harbor Hog Creek Rd, East Hampton, NY⁠
Experience the essence of the legendary Apollo Theater with DJ Cassidy, Doug E. Fresh & more!⁠
⁠
⁠
🦈 50th Anniversary of JAWS Celebration – Montauk⁠
📅 Sun, Aug 24, 2025 | 12pm–7pm⁠
📍 Shark Bar Montauk, 2167 Montauk Hwy⁠
Screening, live music with Molly Scheider, themed cocktails, shark merch 🦈 — all to benefit Hayground School.⁠
⁠
⁠
😂 Chelsea Handler at WHBPAC⁠
📅 Fri, Aug 22, 2025 | 8pm⁠
📍 WHBPAC, 76 Main St, Westhampton Beach, NY⁠
A night of comedy with Chelsea Handler!⁠
⁠
⁠
🎵 The Knocks at Surf Lodge⁠
📅 Sat, Aug 23, 2025 | 4pm⁠
📍 The Surf Lodge, 183 Edgemere St, Montauk, NY⁠
The Knocks bring their signature groove to the Hamptons.⁠
⁠
⁠
🌅 Generation S.O.S – Live From Water Mill Fundraiser⁠
📅 Sun, Aug 24, 2025 | 5pm–8pm⁠
📍 Water Mill, NY⁠
Featuring Jason Biggs, Luke K, & MC Sophie Sumner.⁠
⁠
⁠
🇬🇷 Mykonos Nights at Calissa⁠
📅 Fri, Aug 22, 2025 | 10pm⁠
📍 Calissa, 1020 Montauk Hwy, Water Mill, NY⁠
End-of-summer vibes with DJs, drinks & dancing.⁠
⁠
⁠
👜🐶 Bark Jacobs by Marc Jacobs at The HUB⁠
📅 Sat, Aug 23, 2025 | 11am–7pm⁠
📍 The HUB, 2183 Montauk Hwy, Bridgehampton, NY⁠
Shop Marc Jacobs & get your pup’s portrait or initials hand-painted on your accessories.⁠
⁠
⁠
🐾 Wags & Walks’ Party Cruise⁠
📅 Sun, Aug 24, 2025 | 3pm–5pm⁠
📍 Easy Breeze Cruises, 462 W Lake Dr, Montauk, NY⁠
Cruise Montauk waters with cocktails & adoptable pups.⁠
⁠
⁠
🎨 5th Annual Celebrating Creatives of Color⁠
📅 Sat, Aug 23, 2025 | 11am–5pm⁠
📍 The Church, 48 Madison St, Sag Harbor, NY⁠
Showcasing artists & authors of color, with works available for sale.⁠
⁠
Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #weekend #hamptonsclassic #jaws #montauk #apollotheater⁠
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