The LDS Ancestral File shows Roger PRESTON of Ipswich, MA, as the son of Roger PRESTON (who died in 1638) and Alice PARRY, of Up-Ottery, Devonshire, England.⁴   The ancestry of Roger PRESTON of Up-Ottery is given by William Bowker Preston in his book, The Preston Genealogy.⁵  He shows a Roger PRESTON, Jr., of Up-Ottery, son of Roger and Alice (PARRY) PRESTON, with a wife named Martha.   The wife of Roger PRESTON of Ispwich was named Martha; and, although William Bowker Preston does not come right out and say that his Roger PRESTON, Jr., is Roger PRESTON of Ipswich, he certainly leaves the door open to that interpretation — and many have entered.  I have, however, yet to find proof that they are the same individual.  In fact, there is proof that they are not.

According to Coldham⁶, there was a lawsuit recorded in 1649 in London involving Roger PRESTON:
 

This Roger Preston certainly sounds like the Roger Preston, Jr., who was son of Roger Preston, Sr., "of Up-Otterly, Devon," who died in 1638.  But if he is, how can the fact that he came back to England from Virginia — not Massachusetts — be explained?

Still referencing Coldham⁶, there is a Roger Preston in the early "censuses" of Virginia (ages are shown after the name, followed by ship and date of arrival, when known — apparently, "Jordan's Journey" is a placename):
 

If this Roger Preston was 21 years of age on 20 Jan 1625, then he was born in either 1604 or 1603, depending on whether he'd had his birthday yet that year.   Surely, it is this Roger Preston, the one born 1603/4 who went to Virginia in 1621 — not the one born 1613/4 who went to Massachusetts in 1635 — who is the one who returned to England in 1638 upon the death of his father and who filed a lawsuit in London in 1649. This man is Roger Preston, Jr., of Up-Otterly.

And now the interesting question is:   How did the son of a landed gentleman end up an indentured servant in Virginia? And what was the outcome of the lawsuit over his father's estate? Did he win, regain the family lands, and stay in England? Did he dispose of the estate and return to the New World with money in his pocket?  Or did he lose his case?

1.  The Preston/Lindsey Trail.  1995.  Self-published by Rosaline Preston (17369 Road 6 SE, Warden, WA 98857) and Carol Huber  (10508-A Witter Springs Rd., Witter Springs, CA 95493).

2.  John C. Hotton.  1931. The Original Lists of Persons of Quality.  G.A. Baker & Co., Inc., NY.  On p. 35:

3.  Peter Wilson Coldham.  1988.  The Complete Book of Emigrants, Volume 1, 1607-1660.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-350), citing E157/20, Public Record Office (Chancery Lane, London WC2A 1 LR, England):

4.  LDS.  Family Search: Internet Genealogy Service:  AF - Ancestral File (online at FamilySearch.org). 

5.  William Bowker Preston.  1900.  The Preston Genealogy: Tracing the History of the Family from about 1040, A.D., in Great Britain, in the New England States, and in Virginia, to the Present Time.  Self-published (online at GenealogyLibrary.com).  The Preston pedigree based on William Bowker Preston's book is posted on my web site under the title, Descendants of Leolphus de Preston of Scotland. 

6.  Peter Wilson Coldham.  1988.  The Complete Book of Emigrants, Volume 1, 1607-1660.  Genealogical Publ. Co., Baltimore, MD (Broderbund CD-350), citing C6/42/94 and C24/727/114, Public Record Office (Chancery Lane, London WC2A 1 LR, England).