Cary was born in Warwick County and was the son of(d. 1667) and Anne Taylor Cary. His father immigrated to Virginia from Bristol, England, probably early in the 1640s and became a member of the governor’s Council before mid-March 1664. After his father’s death, the orphaned Henry Cary and his underage brothers inherited Warwick County plantations, his being called the Forest, and that of (d. 1709), surveyor general of Virginia and member of the for more than twenty years, being called Richneck. By the spring of 1671 Cary had married Judith Lockey. They had three daughters and two sons, the elder of whom, Henry Cary (d. by March 2, 1750), became one of the principal building contractors in the region.
There is no evidence that Cary trained in the building trades in preparation for his career, but the loss of the Warwick County records leaves many aspects of his life poorly documented. His first recorded involvement in construction was a proposal to thein December 1695 to build a platform for the defensive cannon at the new port of Yorktown. In 1697 Cary contracted for 28,000 pounds of to erect a new courthouse for York County on the north side of Main Street in Yorktown. He completed the work by the end of the year. Given its relatively low cost and the speed with which it was constructed, the building probably resembled other courthouses of the period, a frame structure with exterior clapboard sheathing and a few windows lit by wooden casements. The building was replaced with an arcaded brick courthouse early in the 1730s.
With this public building experience and perhaps other private commissions that have left no documentary trace, Cary seized the opportunity to secure the contract to build the colony’s new Capitol after the previous statehouse inburned in October 1698. Cary’s petition to oversee construction of the new brick building in Williamsburg was granted in November 1699. During the next half-dozen years, Cary procured materials, supervised dozens of skilled and unskilled workmen, and coordinated the erection of the two-story, double-winged building at the east end of Duke of Gloucester Street. Although he was not the designer, he was able to shape many of its details. In the midst of this project, Cary also erected a prison for the colony, a one-story brick building located a few hundred yards north of the Capitol. He had completed both structures by 1705, to the satisfaction of government officials, not an insubstantial feat in a colony where public works on that scale had not before been attempted.
Cary’s achievement led to his appointment in 1706 to oversee construction of the new house for the governor. He may have been responsible in part for the building’s design as well. Under his direction between 1706 and 1708, the two-story, double-pile brick residence rose at the north end of what became Palace Street. Cary’s success with the Capitol did not guarantee success on his second ambitious undertaking. By 1708 he had exhausted all the money appropriated for the building, his craftsmen threatened to stop work unless they received back wages, and roofing slate arrived from England so severely damaged that it proved unusable. Although the General Assembly reluctantly advanced money to keep the project from foundering, Cary was forced to move into the unfinished house to protect it from damage, an action the Council perceived as an attempt “to maintain his whole family at the publick charge.” When Lieutenant Governor Alexander Spotswood arrived in Williamsburg in 1710 and discovered that his residence was an unfinished shell and that there was little money left to complete it, he turned his wrath on Cary for mismanaging the project and charged that he was incapable of the business of building. The Council complained of Cary’s extravagance in April 1711 and in December ordered him to present an account of his expenses. Soon afterward Cary was dismissed from the project.
The fiasco of the governor’s house ruined Cary’s chances for further government work. In 1711 he proposed to supply materials for the new Bruton Parish church, but Spotswood considered the price too high and ensured that the contract went to a competitor. Recognizing that his career in Williamsburg was at an end, Cary retired to his plantation in Warwick County. Possibly he continued to work outside the capital on occasion. In 1719, for example, Richard King’s agreement to erect the Swan Tavern in Yorktown allowed him to bring in Cary to appraise the building if the compensation agreed on did not cover the construction costs. Except for a fragment of the prison, all the public buildings that Cary erected in Williamsburg have been destroyed, making it difficult to judge the quality of the work that Spotswood condemned. Cary died, probably at his Warwick County plantation, on an unrecorded date before September 1, 1720, when his will was proved in the county court.