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John's father's will was written 1 Jan 1657 and references his son Francis and his wife's pregnancy with John but the The Generations of Virginia states this child was a daughter named Mary, however this was Bartholomew Ennels daughter.
After his father died, his mother married Bartholomew Ennalls.
Francis' will, written 01 Jan 1657 and Proved: 14 Aug 1659, mentions widow Mary, who subsequently married Bartholomew Ennals[1], founder of the Maryland family of that name, son Francis and "the child my wife now goes" who was John H., afterwards of Maryland.[2][3]
By 1669, Bartholomew Ennals had transported himself, his wife Mary, stepson Francis Howard (aka Heyward) and children Bartholomew Jr, Mary, Thomas, and William from Virginia to Maryland. [4]
"John Heyward (Howard) and his brother, Francis Heyward, were early residents of York county, Va. Mary, the widow of Francis Heyward, married Bartholomew Ennalls of Maryland, formerly of York county, Va. Francis and John Heyward, sons of Francis Heyward of Virginia, were living in Dorchester county, Md., in 1680. John Heyward, first named, was the ancestor of a prominent family in Virginia." [5][6],
"In reference to the Heywards, there is, in court, a letter of record from Francis and John Heyward, of 25 Oct 1680, to William Arnold, authorizing him to give possession of some land in Pocoson, York County, Virginia, to Francis Heyward's [step]father - Bartholomew Ennalls."[7]
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History of dorchester page 288 Might shed some light on this family