In the Spirit Of Kelly Killoren Bensimon: Her Real Estate Reign + Reinvention
Interview-Jennifer MacLellan | Creative Direction-Vanessa Coppes | Photography-Miguel Pichardo | Makeup-Chris Lanston | Hair-Katie Rote | Stylists-Mindy Gura + Paula Orlan | The Style Duo | LOCATION-Home of Scott Weissman | CEO, GREY/VEN | Shoot Assistance- Aseel Shilleh, Alexis Lombardo, Emily Zuckerberg, Alessandra Agostino, Ellie Battipaglia, Gianna Repole
Coverup and swimsuit: Grey/Ven
Necklace : Donna Moda, Westwood, NJ
From her early days gracing the runways and pages of glossy magazines to writing bestselling books and now brokering multimillion-dollar deals, Kelly Killoren Bensimon is living proof that evolution and elegance go hand in hand. With the Hamptons as both her muse and her home base, the model-turned-author-turned-real estate powerhouse has built a life—and a legacy—rooted in passion, purpose, and unmistakable style.
But it’s not just business acumen or television fame that defines her. Whether she’s closing deals from Manhattan to Montauk, raising two daughters, or sharing life lessons on her iHeartRadio podcast, Kelly exudes the kind of grounded energy that comes from living intentionally. In this exclusive BELLA cover story, she opens up about the chapters that shaped her, the lifestyle she’s built, and why she’s entering her “era of yes” with confidence, gratitude, and just the right amount of rosé.
From model and author to powerhouse in luxury real estate, your evolution has been anything but ordinary. What has grounded you most through all these transformations?
Gratitude. Every chapter—whether it was walking the runway, writing books, raising my girls, or selling eight-figure homes—has taught me something. What grounds me is knowing that I’ve been given this incredible platform to constantly evolve, learn, and be better. I see every new direction not as a reinvention, but a deeper reflection of who I’ve always been.
Your first book, IN The Spirit of the Hamptons, captured the magic and lifestyle of this iconic destination. Looking back, how does your relationship with the Hamptons feel different—or deeper—today?
That book was such a love letter to the Hamptons. Back then, I was capturing its energy through photography and intimate storytelling. Now, I’m helping people build lives here—finding homes where they’ll create memories of their own. It’s a deeper connection now, more personal. The Hamptons isn’t just a place I write about—it’s part of who I am. It’s where I raised my family; it’s the place where I feel safe and whole.
Sweater, swimsuit, and blanket : Grey/Ven
“I’m proud that I’ve been able to use that visibility to empower myself and others. I’m more than the girl with jellybeans in her bag.”
-Kelly
You’ve built an impressive real estate portfolio, especially in the Hamptons and New York City. What do you think sets you apart as a broker in such a competitive, high-stakes market?
I’m a licensed broker in New York and the Hamptons, a real estate agent in Florida and California, and I represent properties abroad—from Paris and London to Ibiza. I represent the best of the best: the best clients, the best properties, and the best lifestyle opportunities. What truly sets me apart is that I lead with lifestyle and long-term vision. I believe in real estate as a vehicle to maximize generational wealth, and I help my clients see beyond the sale—to what their investment can do for their future. Whether it’s oceanfront serenity or city sophistication, I understand what luxury feels like, and I deliver it with heart and a strategic mindset.
People first got to know you on The Real Housewives of New York, but you’ve carved a path that goes far beyond reality TV. What’s a side of yourself the public doesn’t always see, but you’re proud of?
RHONY was such a full-circle gratitude moment. It gave me a global platform—and I’ve used that to build upon my foundation and maximize it into what I have today. Beyond that, I had the privilege of making lifelong friends who continue to inspire me. What people don’t always see is the academic, the businesswoman, the mom who shows up for her daughters every single day. I’m proud that I’ve been able to use that visibility to empower myself and others. I’m more than the girl with jellybeans in her bag.
Your personal style has always been effortlessly chic. How has your approach to fashion and beauty evolved over the years, especially as you continue to redefine what it means to be stylish at every stage of life?
I’ve always believed in dressing for the feeling, not the trend. Style, for me, is about confidence and comfort—whether I’m in Chanel flats or barefoot in the sand. As I’ve grown, I’ve embraced a more natural, low-maintenance kind of beauty. And I love showing that elegance doesn’t have an expiration date. Smart and sexy are ageless.
Wellness and balance seem to be at the core of how you live. What are your daily non-negotiables for feeling strong physically, mentally, and emotionally?
Running—not walking—is my therapy. I have to move every single day; it keeps me grounded, focused, and energized. Mentally, I’m very intentional about my support system. On my podcast, I Do, Part 2 on iHeartRadio, I work with therapists, lawyers, and other professionals who support me on my journey to finding my forever person. That network has been incredibly grounding, helping me make the right choices for my future and my family when it comes to picking a partner. I also wrote a book called I Can Make You H.O.T., which includes my Supermodel Diet—H.O.T. stands for Healthy Options Today. It’s all about making smart, feel-good choices that are easy to incorporate into everyday life. I use red light therapy, which has been incredible for treating my psoriasis and keeping my skin glowing. And because I believe in joy as much as discipline, I always make time for Sunday Fundays: guacamole, chips, and a cold Corona or a crisp glass of rosé. Balance is beautiful.
What’s next for you, both personally and professionally? Any exciting projects, passions, or goals on the horizon that you can share with us?
So many exciting things! I’m expanding my real estate work globally, and I’m also working on something fun in the wellness space tied to my Supermodel Diet and H.O.T. philosophy. I'm focused on helping people feel good in their bodies and in their spaces. But most of all, I’m in my era of yes—I’m constantly saying yes to the projects, people, and passions that bring joy, creativity, and purpose.
Follow Kelly on Instagram @kellybensimon.
Sweater dress: Grey/ven
Shoes: Pelle Moda
Hat: Mix Brown