Edmund was one of the original settlers of Quasca Cunquen, afterward Newbury, where each of the first settlers was granted a house lot of at least four acres, with a suitable quantity of salt and fresh meadow. In addition to this, he had a grant of twelve acres, which shows him to have been one of the eighteen principal pioneer settlers. Edmund lived near the old town bridge in Newbury, where he kept a tavern. By trade, he was a silk dyer. He was Ensign in 1639, Lieutenant in 1645, and Captain of the Militia under William Gerrish. He and Sarah moved to Boston about 1650.

Edmund and his wife Sarah (Dole) Greenleaf had ten children, all baptized at St. Marys la Tour in Ipswich, County Suffolk, England:

• Enoch, bpt. 1 Dec. 1613; d. 1617.
• Samuel, b. date unknown; d. 1627.
• Enoch, b. about 1617/8; m. Mary -----.
• Sarah, bpt. 26 March 1620; m. William Hilton, son of William Hilton.
• Elizabeth, bpt. 16 Jan. 1622; m. (1) in 1642 or earlier, Giles Badger; m. (2) 16 Feb. 1648/9 Richard Browne.
• Nathaniel, bpt. 27 June 1624; d. 1634.
• Judith, bpt. 2 Sept. 1625; m. (1) Henry Somerby; m. (2) Tristram Coffin, Jr.
• Stephen, bpt. 10 Aug. 1628; m. (1) Elizabeth Coffin, daughter of Tristram Coffin; m. (2) Mrs. Esther Swett.
• Daniel, bpt. 14 Aug. 1631; d. 5 Dec. 1654.
• John, b. about 1632; m. Hannah Veazie, daughter of William Veazie.

Stephen was a representative to the General Court from Newbury, 1676-1686. He was appointed Ensign in 1670, Lieutenant in 1685, and Captain of the Militia in 1686. "As a Captain of the Militia, he went with the disastrous Phips expedition against Port Royal, 1690, to Cape Breton, and was there wrecked in a vessel and drowned in company with nine others."

Captain Stephen and his first wife Elizabeth (Coffin) Greenleaf had ten children, all born in Newbury, MA:

• Stephen, Jr., b. 15 Aug. 1652; m. (1) Elizabeth Gerrish, daughter of Captain William and Joanna (Lowle) Oliver Gerrish; m. (2) Mrs. Hannah Jordan.
• Sarah, b. 29 Oct. 1655; m. Richard Dole, son of Richard Dole.
• Daniel, b. 17 Feb. 1657/8; d. 1659.
• Elizabeth, b. 9 April 1660; m. Col. Thomas Noyes, son of James Noyes.
• John, b. 21 June 1662; m. (1) Elizabeth Hills, daughter of Joseph Hills; m. (2) Lydia (Frost) Pierce, daughter of Charles Frost.
• Samuel, b. 30 Oct. 1665; m. Sarah Kent, daughter of John Kent.
• Tristram, b. 11 Feb. 1667/8; m. Margaret Piper, daughter of Nathaniel Piper.
• Edmund, b. 10 May 1670/1; m. Abigail Somerby, daughter of Abiel Somerby.
• Judith, b. 23 Oct. 1673; d. 1678.
• Mary, b. 6 or 8 Dec. 1676; m. Joshua Moody, son of Caleb Moody.

Stephen, Jr. was a prominent man in public affairs. He was a selectman in Newbury in 1675-76. Like his father, he was Ensign, appointed Lieutenant in 1685, and Captain of Militia in 1689. He served in King Philips War on the Connecticut River and was wounded in the Battle of Hatfield, MA. He was famed for his services in the Indian wars and was known as "the great Indian fighter." The following notes give an account of some of his experiences with the Indians:

"In 1689, he was appointed agent of the state to treat with the Indians at Pennacock. May 18, 1695, he files a petition for relief, and presents the bill for professional services of Dr. Humphrey Bradstreet, which reads: 'Bill for curing Capt. Stephen Greenleaf, who was wounded while moving a family who had been taken from Newbury by the Indians.' On the fifth of March, 1696, Captain Greenleaf addressed the following petition to the general court: 'The petition of Captain Greenleaf, of Newbury, Humbly Showeth: That upon the Seventh of October last, about three o'clock in the afternoon, a party of Indians surprised a family at Turkey Hill in said town, captured nine persons, women and children, rifled the house, carrying away bedding and dry goods. Only one person escaped, and gave notice to the next family, and they to the town; upon the alarm your petitioner with a party of men pursued after the enemy, endeavoring to line the river Merrimack to prevent their passage, by which means the captives were recovered and brought back. The enemy lay in a gully hard by the roadway and about nine at night made a shot at Your Petitioner, and shot him through the wrist, between the bones, and also made a large wound on his side, which would have been very painful and costly to your petitioner in the cure of them, and have in a great measure utterly taken away the use of his left hand, and wholly taken off from his employment this winter. Your petitioner therefore honorably prays this honorable court that they would make him such compensation as shall seem fit; which he shall thankfully acknowledge, and doubts not but will be an encouragement to others, and possibly to relieve their neighbors when assaulted by so barbarous an enemy, And your petitioner shall every pray.'

"(Signed) Stephen Greenleaf"

"March 6 ---- Read and voted that there be paid out of the province treasury to the Petitioner the sum of forty pounds."

This is said to be the only instance in which the Indians attacked, "captivated," or killed any of the inhabitants of Newbury.

Captain Stephen Jr. and his first wife Elizabeth (Gerrish) Greenleaf had ten children, all born in Newbury, MA:

• Elizabeth, b. 12 Jan. 1677/8; m. Henry Clarke, son of Nathaniel Clarke.
• Daniel, b. 10 Feb. 1679/80; m. Elizabeth Gookin, daughter of Samuel Gookin.
• Stephen, b. Aug. 1682; d. 15 Oct. 1688.
• William, b. 1 April 1684; d. 15 April 1684.
• Joseph, b. 12 April 1686; m. Thomasine Mayo.
• Sarah, b. 19 July 1688; m. Richard Kent.
• Stephen, b. 21 Oct. 1690; m. Mary Macrest, daughter of Benoni Macrest.
• John, b. 29 Aug. 1693; m. Sarah Smith, daughter of James Smith.
• Benjamin, b. 14 Dec. 1695; probably died young.
• Moses, b. 24 Feb. 1697/8.