One of the earliest residents of Virginia Beach was Captain Adam Thoroughgood, who persuaded 105 people to settle with him in the new Virginia colony and had a land grant for 5,350 acres. He gave the name of Lynnhaven to the Bay and River he settled on, after his home town in England. His four room brick house is still standing and has been restored as a museum, the oldest surviving brick house in America. Among the 105 settlers that accompanied him was Augustine Warner, a direct ancestor of both George Washington and Robert E. Lee. Thoroughgood became a prominent citizen of the Virginia Colony, and was an elected member of the House of Burgess, the Governors Council, and a Justice of the Court.

The slow growth of early Virginia Beach was unusual for an area with its advantages.  There were relatively few Indians in the area, large numbers of wildlife, fertile soil and many rivers suitable for transportation. Virginia beach was still a sparsely settled rural area when the Revolutionary War broke out. Most of the war passed the area by, with only one small skirmish taking place, with one man killed. Many historians feel that a naval battle off the shores of Virginia Beach may have been a turning point of the war, when a French fleet under the command of Admiral De Grasse defeated a British fleet that was to supply General Cornwallis at Yorktown. Without these supplies and with no chance of being evacuated by the British Fleet, General Cornwallis was forced to surrender at the Battle of Yorktown on October 19, 1781. The Battle of The Capes monument shares a place at Fort Story with the First Landing Site.

The small resort area was created in 1880 and Virginia Beach was incorporated as a town in 1906, but most of Princess Ann County was undeveloped at the time. With the coming of World War II, the Navy established the Oceana Naval Air Station and expanded the Norfolk Naval Base. This brought a sharp increase in the population of the county, as well as permanent jobs. Virginia Beach and nearby Norfolk both grew rapidly in the years following the War. In 1963 Virginia Beach annexed all of Princess Ann County into the city limits, becoming the largest city in the Commonwealth of Virginia with 310 square miles.