Through his commercial activities he acquired considerable wealth, and was able to loan money to Queen Elizabeth I and purchase properties in several counties as well as houses in and near London.

[6][7] As a member of the Company of Merchant Adventurers he exported English cloth, and imported from abroad coarse materials such as fustian and buckram and luxury fabrics such as camlet and silk.

[10] In 1572 he was elected to Parliament for the City, where he played an active role on several committees, and in the same year became President of St Bartholomew's Hospital, a post he continued to hold until his death.

[13] According to Jay, 'No mention of Sir Rowland's specific services to London can give any idea of his unwearying devotion to the city of his adoption'.

[13] Hayward's increasing wealth from his commercial ventures allowed him to loan money to the Queen,[14] and to acquire considerable property over the years.

[22] Hayward died 5 December 1593 at King's Place in Hackney,[23] and was buried at the church of St Alphage London Wall.

[26] In his will, dated 17 November 1592 and proved 4 March 1594, he left a third of his property to his wife and another third to his children, according to the custom of the City of London, with the remaining third devoted to his own personal bequests, including gifts for charitable purposes.

In 1596, Elizabeth Trentham, Countess of Oxford, purchased it from his executors; she lived in it for more than a decade, and sold it in 1609 to Fulke Greville, 1st Baron Brooke.

[26] Hayward married secondly, when she was only sixteen years of age, Katherine Smythe, the daughter of Thomas Smythe, Customer of London,[6][36] by whom he had a son and a daughter who died as infants, and two surviving sons and four surviving daughters, all young and unmarried at the time of his death:[26] Here lyeth the body of Edward Crayford esq eldest sonne of Sr Will Crayford of Great Mongeham who by Anne his wife one of the daughters of Sr Rowland Hayward thrice [sic] Lord Maior of London who had yssue will [sic: Willm] George Richard Iohn + Anne, he dyed ye 28th of Sept 1615 of his age ye xxxixth vnto whose memorie Anne his wife hath dedicated this.After Sir Rowland Hayward's death, his widow, Katherine, married Sir John Scott, son of Sir Thomas Scott.