On 30 Oct 1797 when Jeremiah was 21, he married Betsey Richardson (57206) , daughter of Zebulon Richardson (44477) (6 Jun 1745-28 Dec 1794) & Abigail Tidd (56908) (10 Jun 1751-). Born on 18 Jul 1776.

Betsey, also known as Elizabeth, Richardson.

On 2 Sep 1804 when James was 26, he married Sarah Frost, daughter of Seth Frost (20 Mar 1760-23 Jan 1814) & Sarah Hill (14 Feb 1761-27 Jan 1848), in Cambridge, MA. Born on 11 Sep 1782 in Cambridge, MA. Sarah died on 17 Sep 1855; she was 73.

Children of James and Sarah (Frost) Winn, born at Burlington, MA:
    i. Charles G. Winn, b. 12 Feb 1805;
    ii. James Winn, b. 1 Jan 1808;
    iii. Albert Winn, b. 14 Jun 1810;
    iv. Samuel Frost Winn, b. 28 Aug 1814;
    v. Newcomb Winn, b. 1816; and
    vi. Sarah Ann Winn, b. 6 Jul 1819.

Moses first married Sally Johnson (56361) , daughter of Capt. John Johnson (56904) (14 Feb 1757-Nov 1792) & Achsah Simonds (42392) (12 Mar 1755-15 Feb 1831). Born on 25 Sep 1784.

On 14 Dec 1807 when Moses was 27, he second married Fanny Damon, daughter of Daniel Damon (18 Sep 1746-) & Lydia Flint (12 Feb 1753-15 Nov 1805), in Woburn, MA. Born on 11 Jan 1779 in Reading, MA. Fanny died in Woburn, MA, on 27 Jan 1864; she was 85.

Francis married Eliza Jackson.