Jay Reeves

Jay brings a thoughtful, well-informed approach to real estate, grounded in deep local knowledge and a strong commitment to client service. Having lived and worked in the Charlottesville area for over two decades, he offers buyers and sellers clear guidance, steady leadership, and skilled negotiation at every stage of the process.

Originally from California, Jay moved to Virginia to be closer to family and spent many years in education, working as an administrator and coach at Woodberry Forest School before settling in Charlottesville. While building his career in education—earning his M.Ed. from the University of Virginia—Jay developed a strong understanding of the local community and housing market after purchasing his first home in the area in 2000. He began his formal real estate career in 2014, initially focusing on commercial transactions, which sharpened his business acumen and market analysis skills.

Today, Jay’s clients benefit from his broad market perspective, attention to detail, and proven ability to negotiate effectively. His awareness of emerging trends and activity in the local business community often provides buyers and sellers with timely insights that help them make confident decisions. Known for his professionalism, responsiveness, and calm demeanor, Jay works closely with clients to achieve their real estate goals on their timeline—not someone else’s.

Outside of real estate, Jay remains deeply invested in youth development and the Charlottesville community, serving as a mentor. When he’s not working with clients, you’ll likely find him staying active on the tennis or padel court, swimming, golfing, or enjoying a walk with family.