We are excited to welcome Jeremy Cunningham to our Maryland sales team! Jeremy brings more than 25 years of executive real estate leadership and a long-standing connection to Deep Creek Lake. After years as a part-time resident and three-time property owner, he and his family made the move from Washington, D.C., to full-time life at the lake in early 2026. Whether he’s on the slopes, in the air, or out on the water, Jeremy embraces everything the lake has to offer. His firsthand experience, strategic expertise and proactive approach make him a trusted guide for clients navigating their next chapter at Deep Creek Lake.
Jeremy Cunningham offers something rare in a resort market: the strategic expertise of a big-city real estate leader paired with the lived experience of someone who has made Deep Creek Lake part of his life for decades. After years as a part-time resident and three-time property owner, Jeremy and his family transitioned from Washington, D.C., to full-time life at Deep Creek Lake in early 2026. That personal journey shapes the way he serves clients today. He understands that choosing Deep Creek Lake is more than a real estate decision — it’s a meaningful shift in how people live, relax, and create memories. His proactive approach makes him a trusted liaison for both lake buyers and sellers.
Jeremy brings more than 25 years of executive real estate leadership to Railey Realty. He previously served as Managing Broker and Regional Vice President for Berkshire Hathaway HomeServices, and before that as CEO and Team Leader for Keller Williams Metro Center. Earlier in his career, he played a key role in Redfin’s early expansion across D.C., Maryland and Virginia. He has also contributed to the industry through service on the Virginia Realtors Professional Standards Committee and through charitable work with Habitat for Humanity and the PenFed Foundation.
Whether clients are purchasing their first Deep Creek Lake property or are current homeowners planning their next move, Jeremy’s guidance is grounded in firsthand experience and a deep understanding of how people live, invest, and evolve at the lake. For him, life at the lake is all about chasing sun and snow, and he provides the expertise to help you catch both.
You can view Jeremy's contact info and current listings here.
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