First, the Virginia Company encouraged wealthy individuals to establish settlements called "hundreds" along the James River. Each hundred was authorized to send representatives to the first General Assembly in 1619. Starting in 1618 and lasting through the 17th Century (and technically until cancelled by the General Assembly in 1779), the "headrights" system authorized the grant of 50 acres for every individual brought to Virginia.1 The colony had an excess of land and a shortage of people, so it was public policy to encourage population growth through immigration and to induce immogration through promises of cheap land.
The headrights system encouraged wealthy individuals to pay to transport indentured servants to Virginia. In theory, the servants would work 5-7 years clearing new land and moving the edge of English settlement further west into the North American continent. The indentured servants did not acquire title to land through their work during their term of service. At the end of their term of indenture, they were given some basic clothing and equipment, and expected to move to the unsettled frontier. They could purchase unimproved land there, "improve" it by cutting down the trees and preparing fields suitable for growing crops such as corn and tobacco. As the forested frontier was converted into farms, indentured servants were transformed into landowners who could provide their children a better opportunity at gaining wealth.
The former servants may have been cash poor, but they could usually buy land on credit from one of the many members of the gentry. The gentry were the wealthy top 5% at the top of Virginia's stratified society. Some were "Cavaliers" who had moved to Virginia during the English Civil War, arriving with sufficient wealth to join the gentry immediately. They acquired large tracts of land and speculated on it gaining in value over time. Speculation was successful when someone was able to acquire title to land at a low cost per acre and then to find settlers willing to pay a higher price per acre for it.
The "headright" system did not provide free land to the initial investor. Transportation costs were as high as six pounds per person in the 17th Century, but abuses of the system allowed some people to expand legitimate claims. Both ship captains and the person paying the transportation costs might try to obtain headrights for the people transported to Virginia, or a claim would be filed for more immigrants than actually arrived in Virginia.
Virginia planters who imported their labor were awarded 50 acres per slave, just as they were awarded 50 acres per indentured servant. Both large and small landowners imported slaves, or purchased them from ship captains who brought them to the colony for sale. George Menefie was the first to claim a large number of headrights for one shipment of slaves, obtaining 1,150 acres for the 23 slaves he imported along with 37 other (white) servants in 1638. The headright claims for the indentured servants listed the names of the individuals, but the claims for slaves rarely identified individual slaves.2
In 1699, after European immigrants became harder and harder to attract, the colony began to sell "headrights" allowing people to claim 50 acres for 5 shillings. Landowners who surveyed tracts and actually acquired patents (certifying their exclusive ownership of a particular parcel) might sell 100 acres for as much as three pounds. Since there were 10 shillings in a pound, that was a 600% markup. 3