The second John married Alice Flint, a most estimable lady, in 1657. He served as a lieutenant in the Indian War, in 1675, and particularly distinguished himself in the memorable fight of Bloody Brook at Deerfield, Massachusetts. He died in 1694 and was succeeded by another John, third in line, who was a farmer, frugal and industrious, and who held many positions of trust in the community. He married Sarah Burrill, of an influential Lynn family. There were two sons, Timothy and Theophilus. The latter was graduated from Harvard and was called to Chebacco parish, first as assistant to Reverend John Wise, and afterwards as minister. There is in the Pickering house a manuscript book on physics bound in leather and illustrated by him. There is also a set of ten chairs made by his hand in 1724. His brother Timothy, who inherited the estate, was deacon of the Tabernacle Church in Salem at his father's death. He was the father of nine children. During his lifetime he added three more rooms on the northern side, raising the roof, which sloped almost to the ground after the fashion of buildings of that period. At the time of these improvements, the eastern part of the house was one hundred years old and the western part eighty. When the weather boards were ripped off, the sills of white oak were so sound that it was decided they would last longer than new ones. One of the peaks was removed at this time because of leaks but was replaced in 1840 by John, the son of Colonel Pickering. When Timothy inherited the estate, he was the first to break the line of Johns. He is described as a gentleman of great piety, firmness of character, and decided convictions. He died at the age of seventy-five and left the estate to his son John, the fifth of the line, who was a bachelor and lived in the old home with his sister, Mrs. Gool, as housekeeper. His occupation was agricultural, but he held several public positions. He represented the town in the General Court for many years, and was town treasurer in 1782. His brother Timothy, who was Clerk of Register of Deeds, entered the Continental Army, and at that time John took his place with the intention of returning the office to him on his return from the war, but he became so accustomed to the work that he kept the position until 1806, when he was compelled to resign through the infirmities of age. It is related of him that at one time he was supposedly fatally ill, and the question of his successor in office coming up, it was proposed to canvass for a candidate. This so enraged John that he recovered from his illness. He was one of the original members of the Academy of Arts and Sciences and was noted for his honesty, industry, and the careful management of his affairs. At his death, the ancestral estate passed to his nephew John (the fifth), the only break in the transmission of the property from father to son.