Simon Whitcomb of Bolton Yeoman acknowledges a deed selling land in Bolton to Joahua Sawyer.
There is a probate file for a Simon Whitcomb of Winchendon Cooper in 1803 [Case 64150]. There is not enough detail in the probate file to identify it as this man or another, as the estate was insolvent, so no heirs were named. It was administered by a Samuel Whitcomb of Templeton, who appears to be Simon's grandson, son of his son Ezra. The occupation of cooper suggests it is not this Simon, perhaps his son Simon who is said to have had no children?