Henry Fleete was born about 1600 in Chatham Court, Kent, to William Fleete, a barrister and his wife Deborah Scott Fleete. Living both in Kent and London he grew up amidst the excitement of colonization for William Fleete had become an adventurer in the Virginia Company of London during its reorganization under the Third Charter in 1612. Thus when in 1619 it was agreed to establish in Virginia a particular plantation of settlers from the county of Kent, young Henry Fleete made plans to join. The ships carrying this Kentish contingent arrived in Virginia in 1621 carrying among them both Henry Fleete and his second cousin Sir Francis Wyatt, the new governor.

Shortly after arrival Fleete met Henry Spellman, trader and interpreter, who had lived with the Indians for two years in his earliest days in Virginia. In 1623 Fleete went traveling with Spellman on a trading cruise up the Potomac when Spellman and twenty of his men were killed and Fleete was taken captive. Spending the next five years as a prisoner of the Patawomekes gave Fleete a knowledge of Indian languages and customs far exceeding that of almost any other colonist.

After gaining his freedom in 1627 he traveled back to England where he told his tales of

Indian lands and possessions and attracted a merchant, William Cloberry, as a backer. For the next four years Fleete took Cloberry's ship, Paramour, on voyages as far north as New England exchanging corn for trade goods to use in trading with the Indians for furs. At the same time he patented his first land, 100 acres, on the Eastern Shore and established trading posts on land which later became Maryland. In 1631 after another trip to England and the acquisition of a new sponsoring merchant, he continued his trading voyages, now on the Warwick, while opening up the beaver trade on the upper Potomac.

   Fleete was very active over the rest of the decade in both public and private activities. He
captured one of William Claiborne's vessels in the conflict over Claiborne's trading activities on proprietary land. He served both colonies in negotiating Indian treaties and was active in the Maryland Assembly. In 1637 he went to England and returned with a shipload of trade goods, but now encountered a Maryland

demand for 10% of his trade proceeds on both the New England and Indian trade. By1639 he had moved to Virginia but maintained property and activities in both colonies. In 1644 he negotiated Indian treaties for Maryland, and in 1645 he was involved in planning and participating in an expedition against the Indians after the second massacre, while also negotiating for corn from neutral tribes.

His life became that of a more traditional colonist after a trip to England from 1646 to 1648 during which time he married a widow, Sarah Burden, with whom he had one son, Henry Fleete. Upon his return to Virginia he found that the lands north of the Rappahannock were opening up and he patented 1750 acres near Windmill Point.

To encourage Indian trade the Assembly authorized both Fleete and William Claiborne to retain for fourteen years the rights to the profits from any trade they might discover where no other Englishman had ever been. However over the ensuing years, Fleete gave up his trading and merchant careers, and became involved in local govenment.

 He helped establish Lancaster County and was one of its first burgesses and a justice of the county court. At the peak he owned 13,197 acres in the Northern Neck. His name appears in a number of court records, the last being in Sept 1660 to discuss protection of Indian settlements. Eight months later there was a reference to his widow, Sara Fleete. Location of his grave is unknown.