Edward Lillie by the recorded births of his children appears to have been in Boston as early as 1663. As he was devoted to the Church of England, it may be presumed that he came from that country, and the date of his eldest child's birth makes it likely that he was born before 1640. This branch of the Lillie family probably lived for a while in Newfoundland, and if so, they are likely to have been of the Devonshire or West-of-England stock, which supplied the first settlers for that Province. They became possessed of real estate at St. John's during the latter half of the seventeenth century, described as "a plantation"—a term signifying full proprietorship.

Edward Lillie married about 1661, Elizabeth, whose maiden name is unknown. He was one of the well known citizens of the town of Boston when its estimated population was from five to seven thousand inhabitants. In 1687 he was one of the sixty citizens whose property was rated at £50 or more,—taking rank with such contemporaries as Elisha and Eliakim Hutchinson, Adam Winthrop, Samuel and Anthony Checkley, and Simon Lynde.[202] Edward Lillie carried on a large business as "cooper," at that period one of the most important industries of New England in its connection with commerce.

Prior to 1670 Edward Lillie had land "in his tenure and occupation" at the North End. He purchased July 8, 1670, an estate at what was then the South End of the town,—a dwelling-house and land. This estate was situated on the south-east corner of Washington and Bedford Streets, and it is in part now (1907) the site of R. H. White's dry-goods establishment. In January 1674 he purchased of Captain Thomas Savage land on Conduit (now North) Street and erected thereon in 1684 a brick dwelling-house. The estate was valued in inventory at £1300.

Edward Lillie's will was dated December 24, 1688, and proved January 7, 1688-9. His wife was probably the "Mrs. Lily" whose death, according to town records, took place January 4, 1705. They had six children.

Samuel Lilly, born March 20, 1663, was the eldest child. June 4, 1683, he married at the age of twenty Mehitable Frary, daughter of Captain and Deacon Theophilus Frary, one of the founders of the Old South Church. Her mother was the daughter of Jacob Eliot, and the niece of John Eliot, the "Apostle to the Indians." Mehitable, was born February 4, 1665-6, and as her father had no sons, his estate was divided between the daughters.

Samuel Lillie, like his father, was a "cooper," but early in life became interested in commerce, sending as early as May 23, 1684, merchandise to the island of Nevis. For the next twenty-three years he was widely engaged in commercial transactions, and was uniformly styled "merchant" in formal documents. After his father's death he bought and occupied the latter's premises at the North End, enlarging them by other purchases.

Mrs. Royall, wife of Isaac Royall and mother of the Loyalist was a cousin of Mrs. Samuel Lillie. During his latter years Samuel Lillie was absent from America quite frequently. It is not likely that he was in Boston from 1708 till shortly before his death.[203] Mrs. Lillie died March 4, 1723. They had eleven children, born in Boston and baptised (except one or two) in the Second church, each a few days after birth.

Theophilus Lillie, the fourth child of Samuel and Mehitable Lillie, was baptized August 24, 1690. He married July 8, 1725, Hannah Ruck (Rev. Cotton Mather officiating). Seems to have done much in settling his father's affairs, but was not engaged in active business.

On the 28th of July, 1732, in Town Meeting, he with others, was appointed a committee to receive proposals, touching the demolishing, repairing, or leasing out the old buildings belonging to the town in Dock Square. The committee to give their attendance at Mr. William Coffin's the Bunch of Grapes tavern, on Thursdays weekly, from six to eight o'clock in the evening. In 1736 he appears as one of the subscribers to Prince's Chronological History of Boston, the list containing, according to Drake, the names of persons most interested at that period in literary concerns.

Hannah Ruck, his wife, was born December 4, 1703 and was the daughter of John Ruck, a successful merchant, a citizen active in municipal affairs and holding municipal offices. Her mother was Hannah Hutchinson, daughter of Colonel Elisha Hutchinson, and aunt of Thomas Hutchinson, the last Royal Governor. A close friendship existed between the two families, and their homes were near together at the North End. This friendship was continued in Halifax, after the Loyalist exodus in 1776.