Serving Queen Anne’s, Caroline, Talbot, Kent & Dorchester Counties
A lifelong resident of Maryland’s Eastern Shore, Samantha Grimes brings unmatched local expertise and a deep commitment to her clients. As Associate Broker and Co-Owner of Chesapeake Real Estate Associates, she specializes in residential properties, farms, lot sales, and new construction across Queen Anne’s, Caroline, Talbot, Kent, and Dorchester counties.
Samantha earned her Bachelor of Science in Paralegal Studies from Wesley College in 1995 and spent seven years as a paralegal before transitioning into real estate. Her legal background gives her a sharp eye for detail and a strong foundation in contracts and negotiations. In 2007, she co-founded Chesapeake Real Estate Associates—one of the few locally owned and independent brokerages in the region.
Dedicated to professional growth, Samantha graduated from the Maryland Real Estate Leadership Academy in 2013 and earned her Associate Broker license in 2017. She and her husband are also active real estate investors, with a diverse portfolio that reflects their belief in the power of homeownership.
Samantha’s leadership and service have earned her recognition within the industry, including the prestigious real estate agent of the Year award in 2011 and the Community Service Award in 2013. She has also served on the boards of several local real estate associations.
She currently lives on a farm in Centreville with her husband Dale and their four boys. Outside of real estate, Samantha enjoys boating, hiking, horseback riding, and embracing all the natural beauty the Eastern Shore has to offer.
Whether you're buying, selling, or exploring your options, Samantha offers personalized guidance backed by experience, integrity, and a true passion for her community.
