Winslow re-enlisted on March 6, 1781, as 2nd Lieutenant and served under Captain Brightman in Colonel Isaac Dean’s Massachusetts Regiment.

He wed Mary Atwood with whom he had children: Job, Polly, Elizabeth, Sally, Jeremiah and Nathaniel. His second marriage to Tamzon Westover produced children, Eliza Jane and George Washington. Winslow died in 1839, in Java, New York. His daughter, Eliza Jane Winslow Lind, was a Charter Member of Job Winslow Chapter, NSDAR in Traverse City, Michigan.