I run an email group called 'Pyemeet' which has about 40 members most of whom are researchers and many of them are related/fit in with several Pye streams. Following message is from Bette (Pye) Wing, one of these members:
I have some information on the Maryland Pyes. Col. Edward Pye lived in Charles Co. and I believe he had a son named Henry, who had several children. According to what I have found, all the white Pyes in MD were slave oweners and several of them also had land interests in Barbados.
Robert Pye, a cousin of Col. Edward, had sugar plantations there and I think other relatives ran the plantations for him. So far I have found no land in Barbados owned by Edward. Col. Edward had children, Charles who returned to
England to take up the Stuart cause, Walter, who seems to have spent much time in Barbados and Henry. There may be been more but this is what I have so far. They married with many of the prominent, favored families of the day but I don't have any married to Lord Baltimore's family. Edward was married to Anne Sewall whose mother married a Baltimore (as a 2nd marriage), but that's as close as I get.
The MD Pyes are very elusive and confusing. They all had the same names for several generations. Mary, Ann and Henrietta were common repeats among the females. I'm trying to connect a William Pye to these Pyes and so far have had absolutely no success.
I'm quite sure that the Henry you seek is not Henry James Pye. It's quite likely it is the Henry, son of Col. Edward, and his family that might be of more interest.
Bette Pye Wing