Jeremy Cunningham

If you are looking for a seasoned sales professional to navigate the transition from city life to lake life, 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 the move himself. After decades as a part-time resident and three‑time property owner, he and his family transitioned from Washington, DC, to full‑time residency at Deep Creek Lake in early 2026. That [...]

If you are looking for a seasoned sales professional to navigate the transition from city life to lake life, 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 the move himself. After decades as a part-time resident and three‑time property owner, he and his family transitioned from Washington, DC, to full‑time residency at Deep Creek Lake in early 2026. That personal journey shapes the way Jeremy serves his clients today. He understands that choosing Deep Creek Lake is about more than real estate - it represents a meaningful change in how people live, relax, and create memories. His proactive approach makes him a trusted liaison for lake buyers and homeowners.

Jeremy brings more than 25 years of executive real estate leadership to the table. Before joining Railey Realty, he served as Managing Broker and Regional Vice President for Berkshire Hathaway HomeServices. Prior to that, he served as CEO and Team Leader for Keller Williams Metro Center and, earlier in his career, played a key leadership role in driving Redfin’s early expansion across DC, Maryland and Virginia. He has also contributed to the industry through service on the Virginia Realtors Professional Standards Committee and through charitable campaigns for 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 offers the expertise necessary to help you catch both.