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Stephen O'Mara was born on 26 December 1844 as the eldest son of James O'Mara, founder of O'Mara's Bacon Company in 1839. Stephen became managing director of the company in 1919, following the death of his brother John O'Mara who had taken over the reigns when their father retired from business. Under Stephen's charge, the family business became one of the most prominent commercial enterprises in Limerick city. Stephen O’Mara was also a prominent figure in local politics. He became a Town Councillor on Limerick Corporation in the 1880s and was elected Mayor of Limerick in 1885. He was the first Mayor of Limerick to be elected on a Nationalist ticket. He also served as High Sheriff of Limerick city in 1888, 1913 and 1914. In national politics, he was a strong supporter of Isaac Butt's Home Rule movement. He later developed a close association with Charles Stewart Parnell and was elected Member of Parliament for Upper Ossory in Kilkenny South for the Irish Parliamentary Party in February 1886. When the Irish National League split from Irish Parliamentary Party in December 1890, O’Mara took the Parnellite side. Towards the end of his life, his moderate political views became more radicalised. He supported the Sinn Fein party in the 1918 General Election and took the pro-Treaty side in 1921, but remained on friendly terms with Eamon de Valera.
Stephen O’Mara married Ellen Pigott in 1867, and the couple had 12 children. From c. 1909 onwards, the family lived at Strand House, where Stephen O'Mara died on 26 July 1926.