About Us

Realtor

Caleb has quickly become one of the most recognized Realtors in Charleston due to his competitive spirit and passion for his clients. Caleb had the number one RE/MAX Team in South Carolina from 2018 all the way through 2024, before moving over to eXp! He has sold over 1,200 homes in his career and has bought, renovated and flipped over 300 properties.

After graduating from Randolph College in VA, where Caleb was a three-year starter on the Randolph College basketball team, he immersed himself in the Charleston area and began pursuing a career in real estate. Over the past 10 years, Caleb’s drive, determination and leadership have allowed him to build a talented team of real estate experts. Caleb’s passion for his team, his clients and the community are evidenced by his work ethic and constant focus on personal and team growth!

Caleb is an active member of NAEA (National Association of Real Estate Advisors), Charleston Young Professionals, CEO Coaching International, The Collective Genius Mastermind, and Legacy Mastermind.

Realtor

Jason Wing is a listing and buying agent for The Caleb Pearson Team, as well as an accomplished sales and business development strategist. Jason’s career has spanned from real estate, to residential development, and even to wealth management. With his strong knowledge of the real estate landscape, he has proven to be an invaluable resource for his customers. Jason has been awarded the distinction of being one of the top producers in the area for three consecutive years!

Jason is a graduate of East Carolina University, with a Bachelor of Science degree in Business Management. He is married to Jamie and has two beautiful daughters. In his spare time, Jason enjoys playing golf, exercising, hitting the beach and spending time with his family.

Realtor

Brandon was born in New Haven, Connecticut, and later moved to Greenville, North Carolina when he was 5 - his sister had Down syndrome, and the family wanted to be in warmer weather for her condition at the time, which was leukemia. Brandon grew up loving sports - he played whatever sport was in season until high school, where he started to focus on baseball. 

Brandon attended community college to study criminal justice, but ended up graduating in the business field. He decided to move to Charleston after being given the opportunity to work for one of the best real estate teams in the Charleston area!

Brandon has a wonderful wife, Lindsey, and two amazing sons! He enjoys everything about Charleston, from the beaches to the incredible history. He's a very hard working, passionate, and shrewd young professional who enjoys helping others! His favorite hobbies are exercising; lifting weights; taking walks with his family, staying on top of the latest real estate developments, watching sports, and reading.

He considers it a true honor to be a part of the best real estate team in Mt. Pleasant and the number three team in Charleston!

Realtor

Anna Caroline was born in Spartanburg, SC and moved to Charleston in 2005. She grew up on the Isle of Palms and attended Porter-Gaud High School. She later went to The College of Charleston where she received a degree in Communications. Anna Caroline has been in sales since she graduated from college, and she's always had a passion and drive for helping others. Anna Caroline married Clay Pearson in 2023 and joined the Caleb Pearson Team shortly after. She is very excited about this next step in her career and can't wait to help people buy and sell in the Charleston area, as it's a place that she loves so much. 

During her free time, Anna Caroline can be found spending time with her family and friends, traveling and enjoying the waters of Charleston on the boat with her husband.

Realtor

Justin was born and raised in Greenville, NC, until he moved to Charleston in 2012 to start a new chapter in his life – he fell in love! He works with his two cousins, Clay and Caleb – the leader of The Caleb Pearson Team. Since these three cousins got into real estate in 2013, they have really taken the market by storm due to their hard work and consistency! 

One of Justin’s main focuses is to push other team members to their full potential. Justin has been a part of over $100 million in real estate volume in the past 12 years. He strives to be an expert in the Tri-County market. He is very passionate about his career and also likes to have a good time while working. Charleston is home for him and his family!

Justin loves Charleston for its beaches and historic character - Justin loves being by the water! He grew up on Lake Gaston in NC and loves water sports. Being from NC originally, he is a fan of the UNC Tarheels, Carolina Panthers, and especially the East Carolina Pirates!

Realtor 

Mark David was born in Belleville, Illinois, in 1994. The youngest of three boys, he’s often referred to by his mom as “the golden child.” Growing up, Mark loved spending time outdoors, staying active, gaming with friends, and attending sporting events. Some of his fondest memories include playing ping pong with his dad and having his mom cheer him on at every sporting event. 

After graduating from high school, Mark attended Missouri State University in Springfield, MO, where he earned a degree in Logistics & Supply Chain Management. This led to a successful seven-year career in Operations Management within the logistics field. 

In 2023, his cousin Eddie, who also works with Caleb, encouraged Mark to take a leap and move to Charleston to explore a career in real estate. Having visited Charleston many times and loving the Lowcountry, Mark embraced the risk and challenge of the move—and hasn’t looked back since. The team’s welcoming, driven, and goal-oriented nature made him feel at home from day one, and he remains deeply grateful for their support.

When working with Mark and his team, clients can expect timely communication, a professional who always prioritizes their best interests, and a positive, can-do attitude.

Education: Missouri State University, Logistics & Supply Chain Management Degree  

Hobbies: Watching sports, playing basketball and golf, weightlifting, taking his dog to Isle of Palms, and persuading his girlfriend to get Mexican food three nights a week  

Fun Fact: Claims the title of “Best Athlete” on the Caleb Pearson Team.

Realtor

Clay was born in Kill Devil Hills, NC in the great year of 1986 and lived there until 1993. In 1993, his parents moved the family to Franklin, Virginia where he spent most of his adolescence. Clay graduated from Southampton Academy in 2005. From 2005-2009 he attended the renowned James Madison University, where he received a Bachelors in Health Sciences. 

After graduating from JMU, Clay moved to Charleston, where he started his career as a real estate agent, first for RE/MAX and now for eXp!

Realtor

Jason Smith is a career real estate agent/broker with over 21 years of experience that has successfully handled a wide variety of real estate transactions at a high volume, with over $300 million sold all over the Northern Virginia and the Carolinas. he specializes in residential sales, residential development, commercial and residential investments, including rehab and multi-family.He lives in Mount Pleasant, SC with my wife and FOUR daughters (yes! four!) and splits his time between the Northern Virginia and Charleston real estate markets.In his free time, he enjoys fitness, golf and photography. 

Listing Coordinator

Alice Horton Sires, a proud native of Charleston, South Carolina, brings over a decade of real estate experience to her role with The Caleb Pearson Team at eXp. As a licensed realtor with an in-depth understanding of the local market, Alice has developed a keen awareness of the unique neighborhoods and communities across the Charleston Tri-County area.

Having grown up in the charming, laid-back town of Summerville, Alice is deeply familiar with the area's serene and welcoming atmosphere. In her younger years, she also enjoyed the vibrant energy of downtown Charleston, exploring its bustling streets and historic charm. Today, Alice and her family—her husband, son, and daughter—call Mount Pleasant home, appreciating its blend of coastal beauty, family-friendly neighborhoods, and close proximity to both the city and the beach.

With more than 10 years in the real estate industry, Alice has honed her expertise and built strong relationships across the region, consistently staying attuned to the trends and dynamics of the ever-changing Charleston market. She’s passionate about helping her clients find the perfect home or investment property, guided by her extensive knowledge of the area's diverse communities, from the historic peninsula to the newer developments in the surrounding suburbs.

Outside of her professional life, Alice cherishes spending quality time with her family. Whether it’s relaxing on the beach, boating through the scenic waters of the Lowcountry, or simply enjoying a quiet day together, Alice values the special moments that make life in Charleston so unique. Her personal connection to the area and her dedication to her clients make her an ideal guide for anyone looking to navigate the Charleston real estate market.

Closing Coordinator

Being raised in South Carolina formed Shay's strong southern values. She developed her hospitality through customer service-related food and beverage jobs, which funded her Bachelors in Psychology at the University of South Carolina. Shortly after graduation she was blessed with a son, which focused her interest more toward a career in real estate. 

After obtaining her SC real estate license in 2011, she practiced administratively, handling marketing, listing coordinating, recruiting, short sale negotiations, REO sales and closing coordinating. In 2013, she moved to Maryland, where she continued her real estate career while working on a team of agents. In 2014, Shay accepted the position as Closing Coordinator on the Caleb Pearson Team, and she has been with us ever since! She is able to apply all of her skills for the best interest of the team. 

In her free time, she focuses on family, fitness, and being outdoors. Her passions include tennis, hiking, traveling, working out, rock climbing, family time, cooking, and reaching goals.