James Riddle

James Riddle is a licensed REALTORA(R) and real estate broker in Delaware and Maryland and Broker of Record with The Parker Group, serving buyers and sellers across the Delmarva Peninsula - with 75+ closed transactions and $25 million in sales volume accomplished in under three years of selling.

His connection to real estate started early. At 15, he was making cold calls after school from a small office in Seaford for a pair of teachers-turned-agents named Dustin and Rachel Parker. He didn't know it then, but that after-school job was the beginning of a career. At 18, he joined a beach rental agency managing roughly 250 properties along the Delaware coast - learning the rhythms of the market, the details that matter to clients, and what it actually takes to run a real estate operation from the inside out. After nearly four years in that role, he reconnected with the Parkers at a local Sussex County REALTORA(R) association event and joined The Parker Group as a sales agent in October 2023. In 2025, he became a licensed broker in both states. That foundation is why he hit the ground running: 25 transactions per year since joining, across markets including Milford, Milton, Georgetown, Bridgeville, Seaford, Rehoboth Beach, Laurel, Millsboro, Easton, Salisbury, and Ocean Pines.

James works primarily with clients navigating complexity - inherited properties, divorce sales, out-of-state relocations, first-time buyers, retirees, and investors acquiring distressed or vacant homes and short-term rentals in the $300K-$750K range. He is particularly skilled at helping clients buy and sell simultaneously and guiding out-of-state buyers through the Delmarva market remotely. What he loves most about this business is the problem-solving. Every transaction is different, every deal has its own complications, and working through those challenges - for buyers, sellers, and the agents he supports - is what keeps him coming back. He holds 10+ five-star Google reviews from clients across those communities.

James was born and raised in Delaware - his family has called Sussex County home for over 300 years. Outside of real estate, he coaches golf at Holy Cross High School in Dover, performs in local theater productions, and plays sports. He lives in Milford with his wife and daughter. If you're buying, selling, or relocating to the Delmarva Peninsula, James is here to support you throughout the chaos.