A woman sitting on a light gray sofa in a modern apartment room with large glass sliding doors, a round mirror on the wall, hanging white pendant lights, and a wooden dining table with small potted plants in white pots.

As of 2026 I’m proud of the empire I’m building. I’ve led global real estate expansions, built investor communities, and helped people at every level — from first-time investors to seasoned entrepreneurs — create wealth through smart real estate moves.

This year marks my 20th Anniversary in the Dominican Republic and with it also the launch of three new brands: The Cheryl Henderson Collective, Cheryl Henderson Real Estate Group and Reset Hospitality.

You’ll see below a timeline of my journey: the bold decisions, the wins, the pivots — and how each one shaped the mission I’m carrying forward today. This isn’t just a bio. It’s a snapshot of a career built on vision, leadership, and relentless action.

 2024-2025

  • In January 2024, I officially launched my Punta Cana Podcast, an exciting new venture that has allowed me to connect with a global audience and share insights on real estate, lifestyle, and living in the Dominican Republic. The podcast has quickly become a go-to resource for expats, investors, and those looking to explore the opportunities Punta Cana offers. I’ve had the pleasure of hosting a wide range of guests, from local entrepreneurs to experts in real estate and veterans' affairs. Through the podcast, I’ve been able to create a platform where stories of inspiration, business, and community come together.

  • One of the exciting developments this year was transforming Hotel Las Flores into a Veterans Wellness Center. The hotel has been reimagined as a space where veterans can stay when they come for tours or medical treatments, creating a welcoming and supportive environment. In addition to lodging, we’ve been hosting activities like community gatherings, game nights, and social events, fostering a sense of camaraderie among veterans.


  • Another major step in supporting veterans was a comprehensive support system for U.S. veterans living abroad, offering essential services including healthcare, physical and mental well-being, emotional support, and real estate guidance, all combined into one Veterans Tour to Punta Cana.

  • In 2024, I launched the International Property Investors Alliance (IPIA), a program designed to make real estate investment in Punta Cana accessible to more people. Members of the IPIA become part of a group of like-minded investors, pooling their resources together to enjoy the benefits of property ownership.

  • The year ends with the launch of Global Rich Strategies, a program where I will share my expertise in real estate, business, and wealth-building strategies. Through this program, I aim to empower individuals to take control of their financial future and build sustainable wealth.

  • Punta Cana Community Care was born from a simple but powerful belief: when we give back, we all move forward.

    This foundation is deeply personal to me. It’s dedicated to four causes that truly touch my heart — our veterans, our children, our animals, and our environment. Each represents a vital piece of the community we’re building and the future we’re protecting.

    Whether it's supporting veterans with the resources they need to thrive, helping children dream bigger and reach higher, rescuing and caring for animals, or preserving the natural beauty of Punta Cana — everything we do comes from a place of love, respect, and responsibility.

    Through hands-on initiatives, rescue efforts, and ongoing community support, we're committed to making a lasting impact here in Punta Cana and wherever else we’re needed.

    Our mission is simple: uplift, support, and nurture those who need it most. Together, we can create a ripple of good that reaches far beyond our shores.

A woman with braided hair, glasses, and a big smile, sitting at a table with a microphone in front of her. She is wearing a blue blazer. Behind her are American flags. She is holding a glass of white wine or champagne in her right hand, and another hand with a glass of white wine or champagne is reaching toward her from the right side of the image.
A woman with braided hair and hoop earrings wearing a pink top, smiling while sitting at a restaurant table with a yellow smoothie in front of her.
A woman with a smile, wearing a green patterned shirt and yellow earrings, is standing on a balcony with her hand resting on a metal railing, with modern apartment buildings in the background and a partly cloudy blue sky.
A woman with braided hair and earrings smiling while looking at her phone in the backseat of a car.

 2023

  • In 2023, I decided to launch my personal brand, Cheryl Henderson Punta Cana, as a way to further connect with my audience and showcase my expertise in real estate and life in the Dominican Republic. One of the major initiatives I worked on was the planning of my Punta Cana Podcast, which I officially launched in 2024.

  • I started planning a special initiative for veterans—Veterans Tours in Punta Cana. These tours began with a strong focus on real estate, giving veterans the opportunity to explore property investment opportunities in the Dominican Republic. In November of 2023, we held our first tour, which, while still focused on real estate, laid the groundwork for what would evolve into a comprehensive medical and wellness program. The tours have since become a cornerstone of the work I do to support veterans in their journey to a fulfilling post-service life.

A group of fifteen people, wearing matching white t-shirts with an American flag design and patriotic text, posing indoors with tropical decor.

 2022

In 2022, we reached a significant milestone with Boardwalk Developments when we completed the construction of Maple Beach and delivered the condos to our clients. It was an incredibly rewarding moment to see the project come to life and hand over the keys to the new homeowners. The entire journey, from breaking ground to completion, was a testament to the hard work and dedication of our team. This success also strengthened our confidence in continuing to pursue future development projects in Punta Cana.

An aerial view of a residential area with modern white and blue apartment buildings, surrounded by greenery and palm trees, with pools on some roofs and a parking lot filled with cars.

 2021

In 2021, I took a huge step forward in my career by launching my own development company, Boardwalk Developments, alongside my husband. It was an exciting and pivotal moment, as we broke ground on our first project, Maple Beach. This project marked the beginning of something truly special, as it was the first of five major developments we are currently working on. The experience of transitioning from real estate to development was both challenging and rewarding, but it allowed us to take a more hands-on approach in shaping the future of Punta Cana.

Three people smiling at a photo event with a backdrop that says 'Boardwalk Developments' and includes a logo of a stylized building and waves.
A woman and a man standing back to back outdoors with trees and blue sky in the background.

 2020

During the pandemic, I saw the world change in so many ways, and the real estate market was no exception. I decided it was time for a change and to take my career to the next level. That's when I made the decision to transition to Keller Williams. Their strong global network, innovative tools, and support for agents were exactly what I needed to continue serving my clients in a new and evolving market.

Group of diverse professionals standing on a staircase in a modern building with large windows, smiling at the camera.
Group of diverse people sitting around a conference table in a modern building courtyard, smiling and talking, with laptops and documents in front of them.

2010-2019

In the midst of the 2008 financial crisis, I saw an opportunity rather than a setback. While many were hesitant to invest, I knew that this could be a defining moment for me in the real estate industry. One of the most defining moments in my real estate career was securing the Master Franchise rights for Keller Williams in the Dominican Republic. I didn’t just join Keller Williams — I launched it in the country with 150 agents and six market centers, creating a strong foundation from day one. That expansion had a global impact, and it solidified my role as a leader in international real estate.

Before that, I was with RE/MAX, which gave me a deep understanding of how to operate within global systems and build high-performing teams. The transition from RE/MAX to launching Keller Williams wasn’t just a step up — it was a power move that changed the game for me and for the region. It proved that I could scale a global brand, lead at the highest level, and make a lasting mark.

Five people standing in front of a hot air balloon with RE/MAX logo, smiling at the camera.
A woman holding a plaque and two awards, smiling in a black lace dress, standing by a sunlit wall.

 2000-2009

I began my real estate career by flipping houses with my ex-husband, which gave me hands-on experience in renovations and identifying investment potential. After obtaining my real estate license, I expanded into residential sales and quickly developed a deeper interest in real estate investing and wealth-building strategies.

Eventually, I made the bold decision to move to Punta Cana, where I could combine my lifestyle goals with real estate and business growth. That move wasn’t just personal — it was strategic. I wanted to live the life I was promoting and help others invest in it too.

Most people remember me as “The Billboard Lady.” I built that brand intentionally — I knew visibility would open doors. But the real shift happened when I transitioned from personal branding and marketing into real estate. That visibility gave me instant credibility in a new space.

CNN news broadcast reporting on Hurricane Matthew in the Dominican Republic, showing a reporter with a microphone and a large billboard with a woman and the RE/MAX Tropical logo.

Early Life

Childhood and Upbringing: I grew up as an "army brat," living in various countries, including South Korea, Germany, and the United States. This global exposure gave me a deep appreciation for diverse cultures and the adaptability to thrive in new environments.

Education: I earned a Bachelor of Science in Electrical Engineering from Washington University in St. Louis, which laid the foundation for my analytical and problem-solving skills.

Corporate Career: After graduating, I joined Procter & Gamble in Cincinnati, Ohio, where I worked in the technology department and excelled in my corporate role.

Framed portrait of a young woman with short, styled hair, smiling, wearing earrings and a dark blazer, with American flags in the background, from Washington University School of Engineering, dated May 19, 1994.
A young man in a tan uniform with a name tag and black belt, standing next to a young girl in a white dress with blue accents, in a room with patterned floors and a framed mirror.