Meet Our Team of Real Estate

Connor Callaway

Broker | Owner

"Would definitely hire him again for any real estate needs. Very responsive, good fee structure, knowledgeable, and easy to work with!" - Arlen S from North Myrtle Beach, 2019

Raised just outside of St. Paul, Minnesota, Connor moved to South Carolina when he was 22 years old.

He played collegiate baseball for a few years prior to obtaining his Real Estate License.

Always searching for innovation, Connor joined a flat-rate company 15 years ago. Connor has worked to grow the company and was co-owner for the last 11 years.  Bringing his wealth of local market knowledge, solid reputation of success in our real estate market, and expertise in negotiating the best deal for his clients, Connor has founded Callaway Estates – The Evolution in Real Estate Sales.  

As a client-focused real estate brokerage that brings real results, his business is consistently growing every day as a result of referrals from past clients and his unique and specialized approach to real estate sales and marketing – tailored exactly to his clients’ needs. 

He brings passion and excitement but most of all an honest assessment and opinion to each transaction.

Whether you are looking to buy, sell or flip Connor has the knowledge and experience to handle all your Real Estate needs.

Rebecca Callaway


A Low Country native, Rebecca has witnessed the tremendous growth that has transformed the beach and its surrounding areas into one of the most sought after destinations. Her exceptional knowledge of the market, coupled with her seasoned insider’s expertise, makes her an unequivocal “go-to” resource for all your real estate needs.

Rebecca graduated at the top of her nursing class at the University of South Carolina and practiced as a Critical Care nurse at our local hospitals for over thirteen years. In 2016, she obtained her license as a Realtor to work alongside her husband.

Rebecca’s contacts and life-long residency leverage her enthusiasm and expertise, enhancing her client dedication. She makes it a priority to listen intently to each client’s interests and goals in order to help identify their perfect home or investment.

In her spare time, Rebecca enjoys playing piano, enjoying the beautiful beaches and rivers, as well as traveling and exploring new places with her husband Connor and their two young children.

Donnie Cundiff


"Donnie was instrumental and assisted in all aspects of our sale and purchase from beginning to end in this process." - Robert M. from Conway, 2019

Donnie is a true South Carolinian with over 30 years of sales and customer service experience including New Construction real estate sales in the Pawleys Island area. 

Living on the South Carolina coast for the past 35 years gives him a wealth of knowledge and in-depth perspective of the local Grand Strand area.

He resides in Pawleys Island with his lovely wife Jennifer and beautiful daughter Sarah.

His passion and dedication to each and every home buying or selling process is second to none.

Chris Caraballo


"Very knowledgeable and takes good care of his clients. He helped us make a good investment, gave us great advice and we would recommend him to anyone! Thanks Chris!"

Chris Caraballo graduated from Coastal Carolina University and is a native of Pawleys Island.

He has been investing in real estate for over 17 years, with a primary focus on new construction and adding value to the many projects he is a part of.

He prioritizes high returns with exceptional customer satisfaction for all of the property investors and home buyers he works with. 

Doug Henderson


"Once we brought Doug on board, within a couple of days, he found the perfect home for us! My husband, who had bought a house before, was shocked at how easy the process for buying this house had been. That is all thanks to Doug's knowledge and skill as a realtor" - Katlyn C from Pawleys Island, 2020


Doug Henderson holds double Masters’ degrees from Coastal Carolina University as well as a Bachelor’s degree from the College of Charleston.

As a true native to the area, he has developed years of local knowledge and key relationships that are leveraged to get the best results for his clients. 

As an active real estate investor himself, he has his pulse on the market nuances that affect your bottom line, whether you are buying or selling.

In his spare time you can find him enjoying time with his wife and two kids, or else he is on the water: boating, surfing or fishing.

Jenna Henderson


Jenna was raised in Pennsylvania and moved to South Carolina in 2008.  She pursued a Masters of Arts in Teaching Science at Coastal Carolina University and has taught in Horry and Georgetown county schools for the last 12 years.   

Jenna became licensed to work alongside her husband Doug.  She pulls from her background in education to meet the needs of each individual client with honesty and integrity,  Her focus on marketing, client relationships, and organization keeps her up to date in today’s market.  

Residing in Pawleys Island she spends her free time with her husband and two kids.  You will find her at the beaches in the summer or volunteering at the Waccamaw schools and her church. 

Kaye Herring

Kaye Herring


Kaye Herring, Realtor

Cathy Reynolds


Cathy Reynolds was raised in Wadesboro, NC and grew up loving and vacationing in the Low Country. In 2008, she moved to the area where she met her husband Ryan and they enjoy raising their two children here. 

Cathy’s background includes being the team leader of the Ultrasonography department at Tidelands Hospital System where she worked for thirteen years.  Her professional skills coupled with excellence with customer service and relations has won her many accolades during her tenure there. 

Cathy lives by the “Golden Rule” and believes honesty and integrity go a long way in both her professional career and everyday life. Thereby, her goal is to exemplify these beliefs as a Realtor. 

In her spare time, Cathy enjoys spending time with family, traveling, singing in the church choir, home decorating, photography and boating on the beautiful Waterway.

Christine Rosow


Christine Rosow has been a licensed Realtor since 1982 starting her career in Connecticut before relocating to sunny coastal South Carolina town of Murrells Inlet. She graduated with honors Bachelor and MBA degrees from University of Connecticut. 

Formerly a licensed Real Estate Appraiser she has a unique understanding of how to negotiate home purchase price for her buyer clients and strategically price homes for her listing clients ensuring high quality results for the clients she works with.  

Christine also serves as a US Coast Guard Licensed Captain and she has most recently managed the Reserve Harbor Yacht Club in Pawleys Island.

In her free time she enjoys golfing and boating so you may see her at one of Pawleys Island’s award-winning golf courses or enjoying a day on one of our local waterways!

Terry Patrick, Realtor

Terry has called the Low Country her home for nearly thirty years now. She is well versed and knowledgable in the ever-changing growth of the area as well as the various medical resources available, having been a Critical Care nurse for over fifteen years within our local hospital system. Her expertise and passion for helping others make her an excellent advocate who listens to your individual needs and situations and works hard to accomplish your Real Estate needs.

She enjoys spending time with her family and enjoying our gorgeous beaches along the strand in her free time.