Chesapeake Virginia Real Estate Chesapeake, Virginia is so many things to so many people, it isn't easy to sum it all up. But, Gateway to Fun certainly comes close. The variety of things to see and do here is amazing and seemingly endless. Whether you concentrate on the city of Chesapeake or include the entire Hampton Roads metro area, there truly is something for everyone. And that makes Chesapeake a perfect getaway destination for couples, families or groups, any time of year. Chesapeake is in the center of so much:  attractions, golf, history, waterways, parks, nightlife, dining, music, culture, sports, and nature of all kinds. Chesapeake is located just 20 minutes from the Virginia Beach Oceanfront, 15 minutes from downtown Norfolk, and 45 minutes from the history of Colonial Williamsburg or the spray and play of the Outer Banks of North Carolina.