Thomas Sheppey arrived in Virginia at age 22 on board the ship Supply, in 1620, and appears in both the 1624 census and the 1625 muster as living at Neck‑of‑land in Charles City. The land patent books show that on 14 November 1635 he patented 250 acres and that when that patent was renewed in 1637 it was increased to 300 acres so that all of the six headrights to which he was entitled had been recognized. In August 1639 he added to his holdings an additional 250 acres elsewhere in Henrico County, and a further patent of 80 acres on Godspeed Fort Creek.

Because by 1640 there was a glut of tobacco on the market, the Assembly felt a need to limit the crop for the year to one and one half million pounds selecting only the best proportionately from all planters and destroying the rest. The Act of Assembly on 6 June 1640 that emphasized the need to address the size and quality of the tobacco crop named Thomas Sheppey, to be a tobacco viewer for the north side of the Appomattox River. In the words of the Act, there was a need for "men of experience and integrity for the careful viewing of each man's

crop of tobacco" to maintain the reputation of Virginia's staple product. This was certainly a mark of the respect in which Sheppey was held.
        Thomas was married to Elizabeth, about whom there is no further information. There is no record of the date of death of either of them. They had one child, a son, Thomas Sheppey, who in later life in 1679 identified himself as being of Bermuda Hundred. Two years later a land patent mentioned his land as being of Varina Parish in Bermuda Hundred.