Thomas Webster was born on 20th March 1800 at Ranelagh Street in Pimlico the son of John Webster a member of George III's household. He trained as a chorister at St George's Chapel, Windsor, and at the Chapel Royal, St James's, London, but, preferring art, entered the Royal Academy Schools in 1821, winning the Schools silver medal in 1825. He was elected a member of the Royal Academy on 10th February 1846. Thomas Webster married twice - firstly to Betsy Millner of Sittingbourne and, after her death in 1859, secondly to Ellen Summerfield of Aylesford at All Souls, Marylebone on 26th July 1860. There were no children of either marriage.

In 1857 Webster moved to the village of Cranbrook, Kent, and became the informal leader of the Cranbrook colony - Frederick Daniel Hardy, George Hardy, Thomas Webster, George Bernard O'Neill, John Callcott Horsley and Augustus Edwin Mulready - that thrived in Cranbrook in the latter half of the nineteenth century. They were a close association of colleagues and friends, and, in the case of the Hardy brothers and G.B. O'Neill, distant relatives. All six were "Genre" painters depicting scenes from daily life, either real or imaginary and, through their work, we have an accurate depiction of the people and homes in the Cranbrook area during the Victorian age. Often the Colony used their children, families and friends as models with the Hardys and Webster focused on rustic interiors and O'Neill and Horsley on picturesque historic architecture. The six painters, who occupied The Old Studio in the High Street, were prolific in their work and exhibited extensively at the Royal Academy and the British Institution.

Throughout his time at Cranbrook Thomas Webster lived at Webster House in the High Street where on 23rd September 1886, he died. A memorial to him by Hamo Thorneycroft was erected, subsequently, at St. Dunstan's Church, Cranbrook