Maurice Chesterton was born in Kensington, London, England on 4 August 1882. He had no formal training as an architect and had begun his career working in the building trade in Chippenham, Wiltshire, and learned the basics of stonemasonry and carpentry. He subsequently moved to Hampstead, London where he designed a number of houses. He is remembered primarily for one building, The Node, a circular thatched dairy building [now offices] in Codicote, Hertfordshire (1928). Whilst working in Chesterton's office in 1927, the architect Elisabeth Whitworth Scott (1898-1972) won the competition to design the new Shakespeare Memorial Theatre in Stratford-upon-Avon and, in 1929, with Chesterton, Alison Shepherd (1898-1972) [formerly Alison Sleigh], and John Chiene Shepherd (1896-1978), she formed the architectural partnership Scott, Chesterton & Shepherd to assist her in building the theatre. By 1934 Chesterton had withdrawn from the partnership to be replaced by John Breakwell (c.1905-1959) as a partner in the practice which was renamed Scott, Shepherd & Breakwell.
Chesterton was a Member of the Society of Architects (MSA) and by 1927 had been made a Fellow of the Royal Institute of British Architects (FRIBA).
In addition to his work as an architect, Chesterton was a painter and between 1921 and 1925 exhibited at the Royal Academy and the Alpine Club in London. His address was given as The Caravan, Bosham, Chichester, Sussex in 1939. He died in Hampstead, London on 7 June 1962.