Map of the Canary Islands (From: encyclopediavirginia.org)
Theodorick Bland was born in 1629. When he got older, he worked as a merchant for England with William and John Bland, his brothers, in Saint Lucar, Spain. Afterwards, Theodorick relocated to Virginia through the Canary Islands and heavily increased his family's wealth and status by becoming the Charles City County Justice, a member of the governor's council, and a member of the Speaker of the House of Burgesses. Once he gained a lot of land in the colony, Theodorick permitted parts of the land to house a courthouse, a prison, and a church. By 1660, he was wed to Anne Bennett, and the couple had three sons: Richard, John, and Theodorick. At one point, Theodorick purchased a section of land entitled Westover from a man named Thomas Paulette, who purchased the land from a man named Francis West after West decided to put the land up for sale due to Native American fighting in 1622.
When his relative Edward Bland passed away, Theodorick acquired the land that Edward left behind, and Edward's son helped work on the property. Edward's widow, Jane Bland, then remarried to a man named John Holmwood, and Holmwood also aided Theodorick with taking care of the land. However, when Theodorick passed away in 1671, a power vacuum appeared, and many people tried their best to stake a claim. To try and halt the power vacuum, John Bland sent Giles Bland to solve the issue. Unfortunately for John, Giles proved to be unsuccessful and got himself hung in Jamestown due to his involvement in Bacon's Rebellion.
Anne Bennett Bland was born in 1639 to Richard Bennett and Mary Ann Utie Bennett. Richard Bennett came to Virginia in 1629, was a part of the House of Burgesses and the Governor's Council, and was the Governor of Virginia from 1652 to 1655. After Anne was wed to Theodorick Bland, Richard gave a part of his acreage in James City County to his son-in-law. At the beginning of her life, Anne resided in Nansemond County, Virginia. She would then migrate with Theodorick Bland to Jordan's Point and Westover after he bought the areas in the 1650s and 1660s.
When Anne and Theodorick had children, Anne made sure they were properly hydrated and fed, as she made them take a cow with them when they headed off to a boarding school in Henrico County. Her caring for her children increased once Theodorick passed away in 1671. She also had to start caring more about her former husband's lands because a power vacuum appeared soon after his death. When Giles Bland arrived from England to try and kick Anne and her children out of their home, trials and debates transpired that would continuously bombard Anne for thirteen years. Relief from these trials and debates only came once she passed away. Fortunately, Anne had friends in higher places, such as Governor William Berkeley and Thomas Ludwell, who made sure that Giles was unsuccessful at taking her lands. She also wed Saint Leger Codd in 1675, and he relocated her to his estate in Wharton Creek in Maryland, where she would pass away in 1687. Codd was a part of the House of Burgesses, had power in Jamestown, and owned lands in Virginia and Maryland. Sarah Bland also harped on Anne about lands in 1682, but even though Sarah did acquire some lands eventually, she could not get Cawson, Westover, a part of Berkeley Hundred, and Jordan's Point from Anne.