Meredith Cohen’s career is proof that it’s never too late to build something extraordinary. After starting on Wall Street and stepping away to raise her family, she re-entered the workforce in real estate. Today, she’s known as “The Westport Expert,” with a standout track record and a business built on trust, 24/7 concierge service and deep local knowledge. She’s Got Issues sat down with Meredith to learn how she turned a midlife pivot into a thriving, top-tier business.
Can you share a bit about your career journey and how you became the Westport expert?
My path into real estate wasn’t linear—it was something I grew into organically. I started my career in finance, but stepped back to focus on raising my family. Years later, when we rented out our home in Westport for the summer, I became fascinated by the process. We were working with a realtor, but I found myself drawn to the strategy, the relationships and the nuance of the market.
Still, the idea of starting over in midlife was intimidating. I hesitated; fear of failure is real at this stage. But when I saw two peers take the leap and enroll in a licensing course, something clicked. I realized I didn’t have to do it alone. That small moment of courage changed everything. Today, all three of us are top-producing agents in the market, which is a constant reminder that betting on yourself is always worth it.
What truly set me apart, though, was my genuine love for Westport. I’m not just selling homes; I’m selling a lifestyle. I’ve always been my town’s biggest cheerleader, and that authenticity resonates. My business has grown through connection, trust and a level of service that goes far beyond the transaction. Oftentimes, I am the first person my clients meet when moving to town. I’m there for my clients in a real, human way—whether that means helping them navigate a move or, in some cases, babysitting their 8-month-old on a weekend. These relationships don’t end at the closing table; they have evolved into lasting friendships.
What was the turning point that made you decide it was time for change?
My daughter was the catalyst. I wanted my children to see me not just as their mother, but as a professional—someone building something of her own. Real estate gave me the opportunity to model resilience, independence and ambition in a very tangible way. That mattered deeply to me.
What were the biggest challenges of starting over in midlife?
Breaking into a saturated market without a built-in network was one of the biggest hurdles. Many agents in my area have deep, multi-generational ties to the community. I didn’t have that advantage. I had to build credibility from scratch, proving my value through results, consistency and expertise.
Another major challenge was adapting to how much the industry has evolved. Social media and digital marketing are now essential tools, and stepping in front of a camera didn’t come naturally to me at first. It felt uncomfortable, honestly, sometimes a little silly but I committed to learning. And that willingness paid off. Video and online presence have dramatically expanded my reach and visibility, allowing me to connect with clients in a more modern, meaningful way. Ironically, a number of my new, younger clients come to me because their parents have seen my Instagram reels and tell them to call me.
How did you prepare yourself for this new career?
My background in finance gave me a strong foundation. At Merrill Lynch, I learned that success comes from trust, guidance and putting the client first, not from pushing a sale. I brought that same philosophy into real estate. I see myself as an advisor, helping clients navigate one of the most significant financial and emotional decisions of their lives. It’s about protecting their assets, not just selling a property.
What do you love most about this stage in your professional life?
There’s something incredibly fulfilling about hitting your stride in a second act. I’m operating at a high level, delivering real value and constantly pushing myself to improve. I’m also naturally competitive, so there’s a certain satisfaction in not only holding my own but outperforming agents who have been in the business for decades.
What is the best part of your job?
Without question, it’s the people. I love being the go-to resource for families who are new to Westport—helping them find their footing, build their lives and feel at home. Over time, those relationships deepen. I’ve become part of their extended community, and in many cases, a part of their daily lives. I’ve made incredible friendships through this work—and have become emergency contacts for at least 10 local families!
What advice would you give to other women considering a second act?
Start before you feel ready. Fear doesn’t go away, you just get stronger than it. The biggest mistake is waiting for the perfect moment, because it doesn’t exist. Growth begins the second you decide to move forward.
What’s next for you as you continue to grow in this role?
Right now, I’m focused on scaling my business while mentoring two women who are at the beginning of their own journeys. Helping others build confidence, develop skills and achieve financial independence is incredibly meaningful to me. It feels like a full-circle moment and a reminder that when women take that first step, it creates a ripple effect far beyond themselves.
Meredith Cohen isn’t just selling homes, she’s built a modern real estate brand rooted in connection, credibility and visibility. From her client-first approach to her growing presence on social media—including standout video collaborations with Ryan Serhant, she’s redefined what it means to show up in this industry. Her success is about more than market share; it’s about relationships and trust. Her journey proves that the best chapters don’t always come first.
