'Genealogical Register of First Settlers of New England', (reprint Baltimore, Genealogical Pub Co 1976) records that John Keep arrived in Springfield MA in 1644 (p.166.) As you say, we don't know the age of John Keep of Longmeadow, so this could be the same man or his father/uncle/cousin. What it suggests, however, is that the original emigration from England occurred in the early 1640's, rather than the 1660's. I think this has confused people, and a new search should begin twenty years earlier. There were quite a lot of John Keeps around in England at that date, so finding the right man is not going to be easy.
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