Rochester's family were 'minor Essex gentry' associated with the Earls of Oxford. According to Ross, Robert Rochester, esquire, was Comptroller of the Household to John de Vere, 13th Earl of Oxford, at a fee of £10 per year, from about 1495 until his death in 1508.
Robert Rochester was born at Terling, Essex, the third son of John Rochester and Grisold Writtle, daughter of Walter Writtle of Bobbingworth. Grisold Writtle's sister, Eleanor, married James Walsingham, and was the mother of Edmund Walsingham, Lieutenant of the Tower of London.
According to Hughes, by 1542 Rochester had been appointed receiver to John de Vere, 16th Earl of Oxford, and was also appointed bailiff of the Earl's manor of Lavenham in Suffolk. By 1551 Rochester had been appointed Comptroller of the Household to Mary Tudor, Henry VIII's elder daughter by Catherine of Aragon. In that year, the Privy Council ordered Rochester to stop any priest from saying mass in the Princess's household; Rochester refused, and was imprisoned in the Tower, and replaced as Comptroller by Sir Anthony Wingfield. The next year, he was released to retire to the county because of his health. He was soon allowed to resume his post as Comptroller.
When the Princess assumed the throne as Mary I, she rewarded Rochester for his faithful service, making him Chancellor of the Duchy of Lancaster and appointing him to the inner circle of the Privy Council. He served as a Member of Parliament for Essex from 1553 to 1555.
Rochester never married. He died 28 November 1557. William Rochester, Sir Robert's older brother received a third of Robert's lands.Robert was buried 4 December at the Charterhouse at Sheen, the house reconstituted by the remnant of the English Carthusians under Dom Maurice Chauncy. He was succeeded in his post as Chancellor of the Duchy of Lancaster by his nephew, Sir Edward Waldegrave (died 1 September 1561), son of John Waldegrave (died 1543) and Rochester's sister Lora (died c. 1545).
- Hughes, Jonathan (2004). "Rochester, Sir Robert (c.1500–1557)". Oxford Dictionary of National Biography (online ed.). Oxford University Press. doi:10.1093/ref:odnb/23918. (Subscription or UK public library membership required.)
- Metcalfe, Walter C., ed. (1879). The Visitations of Essex, Part II. XIV. London: Harleian Society. p. 622. Retrieved 3 July 2013.
- Pollard, Albert Frederick (1897). "Rochester, Robert". In Lee, Sidney. Dictionary of National Biography. 49. London: Smith, Elder & Co. pp. 72–3.
- Robison, William B. (2004). "Walsingham, Sir Edmund (c. 1480–1550)". Oxford Dictionary of National Biography (online ed.). Oxford University Press. doi:10.1093/ref:odnb/28622. (Subscription or UK public library membership required.)
- Ross, James (2011). John de Vere, Thirteenth Earl of Oxford (1442–1513); 'The Foremost Man of the Kingdom'. Woodbridge, Suffolk: The Boydell Press.
- Weikel, Anne (2004). "Waldegrave, Sir Edward (1516/17–1561)". Oxford Dictionary of National Biography (online ed.). Oxford University Press. doi:10.1093/ref:odnb/28433. (Subscription or UK public library membership required.)
- Herbermann, Charles, ed. (1913). "Bl. John Rochester". Catholic Encyclopedia. New York: Robert Appleton Company.