Robert Winchell is a bit of a mystery since as far as I can tell, his home in England, or possibly Wales, has not been located. He is believed to be the son of Thomas Winchell or Wyncoll and Beatrice. One birth location for Robert has been suggested as Dorchester, Dorset, England, but I am not able to find any documentation for that.
Robert and his wife Mary (generally said to be Mary Phelps) arrived in Dorchester, Massachusetts Bay Colony most likely in 1634. He was accepted as a freeman on May 6, 1635 in Dorchester. He acquired several pieces of property there but shortly after, probably in 1637, moved on to Windsor, Connecticut, where he also acquired land, including that given to the original proprietors in 1640. Two children were born to Robert and Mary before they arrived in Windsor, and six more after they made their home there. Mary must have been a busy lady!
Robert served several times on juries for Connecticut and at least once as an arbitrator, but as far as we know was never really involved in the government of the town or the colony. We do believe that he had some education, as he had an old Bible and about 10 books in his possession when he died.
We learn a little more from the inventory. It included two swords and some ammunition, but apparently not a firearm. This indicates that he had been excused from military duty, as all of the militia or training band was required to have firearms at all times.
Robert died March 5, 1667/1668, apparently owing a little more than the value of his estate. However, the oldest son, Nathaniel, did end up with the homestead, and the other sons were left something, even if it was just the forgiveness of a debt. His will was oral, which sometimes means the last illness was sudden and there was no time to call someone who could write it out .
The other thing we can tell about Robert is that he seems to have stayed out of trouble, at least anything major, for there is no reference to him in the court records that I have consulted. He was one of those who came to America and quietly helped build it, supporting his family and giving them a chance to make a better life for themselves.
The line of descent is
David Winchell-Elizabeth Filley
Elizabeth Winchell-John Trumbull
Hannah Trumbull-Medad Pomeroy
Medad Pomeroy-Eunice Southwell
Eunice Pomeroy-Libbeus Stanard
Libbeus Stanard-Luceba Fay
Hiram Stanard-Susan Eddy
Louis Stanard-Mary Alice Hetrick
Etta Stanard-Loren Holbrook
Gladys Holbrook-Richard Allen