Robert Whitcomb was born in England, the son of John Whitcomb and Frances Coggan. He was baptized at St. James, Taunton, Somerset, England, on 20 Dec 1629.
Robert Whitcomb married Mary Cudworth twice. First, they were married in a Quaker ceremony. Torrey shows that they were married at Quebec in 1659., and from later documents, it appears that they eloped. Charges were brought against Robert and Mary for an improper marriage:
"Att this Court, Robert Whetcomb and Mary Cudworth, for disorderly coming together without consent of parents and lawfull marriage, is sentenced to pay ten pounds fine and imprisoned during the pleasure of the Court; and being desirouse to bee orderly married, accordingly were this 9th of March, 1660."
The marriage of Robert Whitcomb and Mary Cudworth by a Puritan preacher was 9 March 1660 recorded at Littleton, Middlesex, Massachusetts.
In his Will, Gen. James Cudworth, the father of Robert's wife Mary, left legacies to "grandchildren Israel, Robert, Mary and James Whitcombe. There was another daughter, born probably after Gen Cudworth's decease, viz. Elizabeth, wife of Daniel Lincoln of Hingham 1710."
The estate of Robert Whitcomb was entered into probate in Plymouth Colony. The Inventory of his estate was taken on 18 Jan 1696/7 and recorded in Court on 12 Feb 1696/7. Widow Mary and Israel Whitcomb were appointed administrators.
 The Inventory mentions what appear to be loans to or from James, Israel and Robert Whitcomb.
Included in the estate papers for the Robert Whitcomb who died in 1704, Robert Sr.'s son, is an undated accounting,  which shows that his estate was disposed of to the widow and children, specifically mentioning:
Joseph Parker and Mary his wife
Others mentioned as receiving small payments were:
As another accounting in that estate file shows that Robert Jr.'s widow was Elizabeth and that his estate was divided between his widow and their three daughters.
Robert was born in 1635.
↑Great Migration 1634-1635, T-Y. (Online database. AmericanAncestors.org. New England Historic Genealogical Society, 2012.) Originally published as: The Great Migration, Immigrants to New England, 1634-1635, Volume VII, T-Y, by Robert Charles Anderson. Boston: New England Historic Genealogical Society, 2011. Page 330
↑ Whitcomb: "Genealogical Research in England," The New England Historical and Genealogical Register. Boston, MA: New England Historic Genealogical Society. NEHGR 68 (Jan, 1914):47 at 63
↑ Torry, Clarence A. New England Marriages Prior to 1700. Baltimore, MD, USA: Genealogical Publishing Co., 2004. Page 804
↑ New Plymouth Colony, edited by Nathaniel B. Shurtlef, "Records of Plymouth Colony, Court Orders, Vol. III, 1651-1661" Records of the colony of New Plymouth in New England William White (Boston, 1855) (reprinted AMS Press, New York, 1968) Accessed at Open Library on 1 July 2016. Vol. 3, Page 206
↑ Whitcomb, Charlotte, b. 1841. (1904). The Whitcomb family in America : a biographical genealogy : with a chapter on our English forbears "by the name of Whetcombe". p.50
↑ Deane, Samuel. "John Whitcomb" History of Scituate, Massachusetts, from its first settlement to 1831 J. Loring (Boston, 1831)Accessed at Internet Archive on 1 June 2016 Page 388
↑Plymouth County, MA: Probate File Papers, 1686-1881. Online database. AmericanAncestors.org (subscription) New England Historic Genealogical Society, 2015. (From records supplied by the Massachusetts Supreme Judicial Court Archives.) Case 22495
↑ which I will refer to as the Questioned Accounting Watt-266 13:57, 2 July 2016
↑Plymouth County, MA: Probate File Papers, 1686-1881. Online database. AmericanAncestors.org. (subscription) New England Historic Genealogical Society, 2015. (From records supplied by the Massachusetts Supreme Judicial Court Archives.) Case 22496
↑ I believe that the Questioned Accounting actually belongs to the estate of Robert Sr.Watt-266 13:57, 2 July 2016