According to his profile, and Anderson, Dolor Davis parents are unknown, so we don't know when they died or what they died of.
He had the inheritance from James Clarke in 1614, ten years before he married Margery Willard, and when her brother Simon was only about 9 years old. Simon married in 1628 to his first wife Mary Sharpe. The inheritance therefore had nothing to do with a relationship between Dolor Davis or James Clarke and the Willard family.
I see no comments on whether he sold his property before departing for New England, but it seems not to have been mentioned in his will, which probably means he had sold it at some point.