About Jeremy Cunningham


Agent Details

Meet Jeremy

Realtor® | Broker | Founding Partner
As the founder of 5x5 Real Estate, Jeremy is realizing a long-standing dream. As a solo agent for many years, he successfully helped a lot of families find and sell their homes. He enjoyed all of it with one exception, he wanted to do “real estate” with others; he was lonely. After 13 years he made the decision to become a Broker and ultimately enter the management or leadership realm of real estate brokerage. Initially, he was a Team Leader and CEO at Keller Williams Realty which eventually led him to an exciting opportunity to be a Managing Broker with Berkshire Hathaway Home Services PenFed Realty.

Jeremy led several offices in Northern Virginia for 4 years and then was promoted to Regional Vice President which he held for an additional 3 years assuming responsibility to manage and lead more offices and agents. He led all brokerage activities including training, recruiting, dispute resolution, staff management, licensing, operations, and growth, amongst many other things. He grew his region into a large operation and oversaw the acquisition and renovation of all the region’s offices.

As a mentor, Jeremy took great pride in helping agents succeed. He spent as much of his time as he could, face-to-face with agents trying to find their magic. He gravitated toward all the positive aspects of the role but was also painfully aware that he couldn’t go as deeply or as thoroughly as he wanted with such a large agent group to serve. He wanted to have the time and ability to go deeper with a smaller group of very select agents.

He also grew frustrated witnessing the dysfunction of teams around the industry and sadly watched many teams collapse. This was frustrating for him as he knew that teams can be amazing with a blend of the right people, transparency, and a mission. He spent years designing 5x5 in his mind, like an architect building a masterpiece. Once the vision was crystal clear, 5x5 Real Estate was born!

Work With Us

Our experience, coupled with our drive to serve with unparalleled professionalism, allows us to represent clients in a very personalized way. Whether buying or selling, allow us to show you how we consistently exceed expectations, one client at a time.

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