Raymond Preston was born on 9 February 1919 in London and attended Cheltenham College from 1932 to 1935, before leaving to begin an engineering apprenticeship with the Gloucester Aircraft Company, where his father was Chief Engineer and Designer. He gave this up the following year and completed his studies to matriculate at Downing College in 1938, studying English under F. R. Leavis. He was President of the College's literary society, the Doughty Society, from 1940-1. He was a conscientious objector during the Second World War and was Senior English Master at Bootham School in York from 1943-8. During this time, he published Four Quartets Rehearsed, a commentary on T. S. Eliot's cycle of poems, broadcast on poetry and wrote criticism for a number of journals including 'The Listener'. He left Bootham in 1951 to continue his broadcasting and writing career, publishing his work on Chaucer in 1952.

He undertook a noviciate in the Community of the Resurrection, Mirfield, from 1952-6, continuing his writing. He was invited as Visiting Professor at Earlham College in Indiana, 1956-7, and was afterwards Assistant Professor at the University of California in Santa Barbara until 1959. He adopted three sons under an American Foster Parents Plan and spent time visiting them in Europe, along with long stays at a number of monasteries, before he returned to America in 1960 as Associate Professor of Trinity College, Washington until 1968. He returned to the family home in Cheltenham around 1970, where he remained until shortly before his death in 1999.