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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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LOCAL EVENTS

Events

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​Saturday Camp AM Drop Off: 12/20 Gingerbread Baking at the Green School!

December 20 @ 09:00 AM - December 20 @ 12:00 PM
The Green School, 287 Merchants Path, Sagaponack, NY 11962
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Dec
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21
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The Polar Express at The Southampton Playhouse

December 20 @ 11:00 AM - December 21 @ 01:00 PM
Southampton Playhouse - 43 Hill Street, Southampton, New York 11968
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20
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20
Dec

Blackbook Art Gallery’s Holiday Party

December 20 @ 11:00 AM - December 20 @ 04:00 PM
245 county rd 39 Southampton ny 11968
20
Dec
20
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20
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Consonance Music Ensemble in Bridgehampton

December 20 @ 01:00 PM - December 20 @ 03:00 PM
Marders - 120 Snake Hollow Road, Bridgehampton, NY, USA
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Parrish Art Museum Guided Tour

December 20 @ 02:00 PM - December 20 @ 03:00 PM
Parrish Art Museum
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Sabrina Rudin x Mill’s Dinner in the Garden

Sabrina Rudin x Mill's Dinner in the Garden

  • The Southampton Playhouse, located at 43 Hill Street in Southampton, has quickly reestablished itself as one of the East End’s most vibrant cultural spaces. After an extensive renovation and a reimagining of its mission, the beloved historic theater is once again bringing people together through film, conversation, and community.⁠
⁠
Under the leadership of Executive Director Maria A. Ruiz Botsacos and Artistic Director Eric Kohn, the Playhouse has evolved into a dynamic hybrid of state-of-the-art cinema and community arts hub—offering everything from IMAX blockbusters and 35mm classics to live performances, themed series, and exclusive talks with filmmakers.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#southampton #southamptonplayhouse #hamptons #film
  • On Saturday, December 13th @heartofthehamptons held their annual Polar Bear Plunge at Coopers beach in Southampton. 

The whole community came together for treats and plunged for a great cause ❄️

#polarbearplunge #coopersbeach #southampton #heartofthehamptons
  • HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
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HamptonsFilm announced that the 34th annual edition of the Hamptons International Film Festival will take place October 2-12, 2026. The 11-day festival will feature screenings and events across the Hamptons.⁠
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The festival will begin accepting submissions via FilmFreeway in February. ⁠
⁠
“As we look ahead to the 34th edition of the Hamptons International Film Festival, we’re excited to continue to bring audiences eleven days of screenings and events across the East End,” said David Nugent, Chief Creative Officer of HamptonsFilm. “Each year, our filmmakers and audiences inspire us to grow, experiment, and celebrate bold new voices in cinema. With submissions opening in February and an exciting slate of year-round programs, from our Screenwriters Lab to SummerDocs and our beloved outdoor screenings, we can’t wait to welcome everyone back this October.”⁠
⁠
⁠
Read the full article at Hamptons.com (Link in Bio)

#hamptonsfilm #filmfestival
  • Check out the Top Hamptons Events This Weekend!

Hampton Ballet Theatre School’s 16th Annual Nutcracker at Guild Hall
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm, 12pm & 5pm
Where: Guild Hall, 158 Main Street, East Hampton, NY
Get into the holiday season with a timeless ballet!

Polar Bear Plunge in Southampton
When: Sat, Dec 13, 2025 • 9am–11am
Where: Coopers Beach, 268 Meadow Lane, Southampton, NY
Celebrate 22 years of getting freezing for a reason! 

Holiday Tour of the Inns
When: Sat, Dec 13, 2025 • 1pm–4pm
Where: East Hampton, NY
Enjoy festive décor and treats across East Hampton’s charming inns.

A Holiday Moment in The Hamptons
When: Sat, Dec 13, 2025 • 2pm–6pm
Where: 26 Montauk Highway, Amagansett, NY
Walk through the evergreens and enjoy cocoa, cider & treats benefiting the Eleanor Whitmore Early Childhood Center.

Amagansett Life-Saving Station’s 3rd Annual Tree Lighting & Toy Drive
When: Sat, Dec 13, 2025 • 4pm–5:30pm
Where: 160 Atlantic Ave, Amagansett, NY
Arts & crafts, cookies, hot chocolate, music — and bring an unwrapped gift for the Kiwanis Toy Drive!

A Christmas Carol: A Live Radio Play — Hampton Theatre Company
When: Fri, Dec 12 – Sun, Dec 14, 2025 • 7pm & 2:30pm
Where: Quogue Community Hall, 125 Jessup Ave, Quogue, NY
A festive classic returns for one weekend only!

Pop-Up Chanukah at Herrick Park
When: Sun, Dec 14, 2025 • 4pm–6pm
Where: Herrick Park, 67 Newtown Ln, East Hampton, NY
Celebrate with songs, donuts, gifts for kids, a dreidel drop & the lighting of the public menorah.

Breakfast with Santa at The Hampton Maid
When: Sun, Dec 14, 2025 • 8am–1pm
Where: 259 E Montauk Hwy, Hampton Bays, NY

Montauk Holiday Concert
When: Sun, Dec 14, 2025 • 3pm & 4pm
Where: Saint Therese of Lisieux, 67 S Essex St, Montauk, NY
Enjoy holiday classics!

Santa Selfies with Birds of Prey
When: Sat, Dec 13, 2025 • 1pm–3pm
Where: Marders, 120 Snake Hollow Rd, Bridgehampton, NY
Meet rescue birds from the Evelyn Alexander Wildlife Center!

Gifts & Carols at the Nathaniel Rogers House
When: Sat, Dec 13, 2025 • 4pm–6pm
Where: 2539 Montauk Hwy, Bridgehampton, NY
Sing along with the Dickens Carolers!

For all event details, see the link in bio. 

#hamptons
  • Saunders & Associates once again demonstrated its commitment to the East End community with the 12th Annual Thanksgiving Donation Drive, which this year reached a record-breaking milestone. ⁠
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Coinciding with Giving Tuesday, the campaign raised an impressive $62,000 for Hamptons food pantries—making it the most successful drive to date and significantly expanding support for local families during the holiday season.⁠
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As the Hamptons’ leading real estate brokerage, Saunders & Associates’ annual Thanksgiving Donation Drive underscores the firm’s longstanding commitment to supporting the Hamptons community all year long.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #saunders #community #foodpantries
  • East Hampton Historical Society hosted its annual House & Garden Tour on Saturday, November 29th. The highly anticipated event invited attendees to uncover five stunning architectural masterpieces in East Hampton. ⁠
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The event quickly sold out, as did the Friday kickoff cocktail party, set at a private, historic home located in the Devon Colony, which had previously been featured on the House & Garden Tour. ⁠
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📸: Rossa Cole⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#easthamptonhistoricalsociety #easthampton #houseandgardentour
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