Cound was acquired in the sixteenth century by Sir Rowland Hayward (c. 1520–93), first son of George Hayward of Bridgnorth – MP for that town in 1529 – by his wife Margaret, the daughter of John Whitbrooke. Sir Rowland dynamically transformed the fortunes of his family who appear, prior to his father, to have been shoemakers. A merchant adventurer, who had previously been trading at Antwerp by 1552, Hayward was importing fustian, camlets and buckram as well as dealing in silks and exporting cloth. He was a truly international London merchant, active in the development of St Bartholomew’s Hospital – where he held a long period as President – and he was Lord Mayor of London in 1570–1, and MP for London in 1572.

With his wealth, he spent heavily in land and, in addition to thirteen manors in Shropshire, he also held one in Wiltshire, one on the Buckinghamshire/ Bedfordshire borders and one in Montgomeryshire. His property at Cound ultimately passed to his daughter, Susan (d. 1592). She had married, as his first wife, Sir Henry Townshend (circa 1537–1621), the son of Sir Robert Townshend (circa 1500–1557), Chief Justice of the Council of the Welsh Marches at Ludlow, and who himself became a member of the Council of the Welsh Marches in 1576.

Sir Henry and Lady Townshend had a son, Hayward Townshend (c. 1577-c. 1603) who was MP for Bishops Castle in 1597 and again in 1601 but, as he predeceased his father, Cound was left to his stepsister, Elizabeth, the daughter of Sir Henry and his second wife, Dorothy Heveningham. Elizabeth had married Edward Cressett (d. 1646) of Upton Cressett and so Cound passed into the hands of the Cressetts in 1623. Although the family continued to own Upton Cressett, Edward’s younger son, James was appointed Rector of Cound (1648–84)8 and was the father of James Cressett, Envoy Extraordinary to Hanover 1693–1703. This outward-looking, well-connected member of the family may have inspired his cousin Edward Cressett (d. 1727) to leave the ancient family seat and to move to Cound, closer to the county town. Certainly Edward, who married Elizabeth Doughty, served Shrewsbury as its MP in 1710–15 and was also High Sheriff of Shropshire in 1702.