If you’re plugged into Hamptons real estate, you start to recognize new names. Then, at a certain point, you realize they’re not “new” anymore. Samantha Rego is there now, having closed $12M in sales in just 2 years. In that time, she has built a real presence and a brand: consistent, polished, active in a market that doesn’t hand anyone credibility for free.
Rego isn’t guessing her way through the business. She came up on Saunders’ marketing side first, which means she understands the mechanics behind exposure, positioning, and what actually moves a listing in a crowded feed. That foundation has shaped her focus on resilience, integrity, and genuine negotiation skills.
Despite her youth, Rego brings an uncommon steadiness, confidence built without bravado. It comes from being intentional about her orbit: surrounding herself with veteran agents, staying close to mentorship, and doing the unglamorous work that separates a “nice listing” from a properly presented one. She talks about networking consistently, investing in the brand, and staying current on laws, regulations, and market nuances.
I appreciated Samantha’s candid responses: the biggest misconception for newcomers isn’t the market, it’s self-doubt. Her advice is simple: learn relentlessly, build your network, partner smartly, and see every deal through.
So, what’s been driving Samantha’s rise—and what can other agents learn from how she’s done it?
What skills do you think will define the most successful agents going forward?
I believe resilience, integrity, and strong negotiation skills will continue to define the most successful agents. In addition, having a well-rounded team behind you, particularly for marketing both your personal brand and your listings, is essential in today’s competitive market.
What brought you to Saunders to build your real estate business?
I began my career in marketing at Saunders & Associates, so I was able to see firsthand the level of support and resources the company provides. Early on, I knew that if I transitioned into sales, Saunders would be my choice. The backing, collaboration, and marketing infrastructure they offer their agents is truly unmatched.
What advice would you give newer agents to build a strong, lasting presence in the Hamptons?
Network consistently, invest in building your brand, and align yourself with a company that provides strong support and resources. Real estate is an ever-evolving industry, so it’s critical to continue learning and stay informed about current laws, regulations, and market trends. Longevity comes from adaptability and professionalism.
What have been the most important lessons you have learned from veteran real estate agents?
One lesson that has always stayed with me is: don’t count your chickens before they hatch. Real estate can be incredibly rewarding, but it requires patience, persistence, and the ability to see a transaction all the way through.
What skills or focus areas have been most important in building your brand?
Building a strong social media presence, consistently networking, and remaining open to new opportunities have been key. Partnering with others has also allowed me to grow, expand my knowledge, and strengthen my business through collaboration.
Where do you think mentorship matters most—negotiation, pricing, client management, or market fluency?
Mentorship is valuable in every aspect of real estate. My background in luxury real estate marketing gave me a strong foundation in presenting properties effectively and maximizing exposure. However, negotiation and navigating complex transactions are skills that evolve with experience. Having mentorship while learning how to structure deals and guide clients through the process has been incredibly impactful.
What’s one of the biggest internal challenges or misconceptions new agents face when breaking into Hamptons real estate?
One of the biggest misconceptions is self-doubt, the belief that they can’t succeed or aren’t experienced enough. I was one of the youngest agents at my company when I began selling independently. I focused on building my brand and expanding my network, while also working both independently and in partnership to strengthen my foundation. I immersed myself in learning about building, zoning, and regulations. Success here comes down to drive, consistency, and being willing to make sacrifices while embracing opportunity.
To learn more about Samantha Rego, click here.
