He was born on 18 September 1819 on the Dalmeny House estate, a few miles west of Edinburgh, his elderly father, William Chesser (1757-1849), being Clerk of Works there.
After spending some years working on the Revesby House estate in Lincolnshire he returned to Dalmeny to fill his father’s shoes on his death.
Through his experience, in 1858, he then gained a post as Superintendent of Works at George Heriot’s School following the death of Alexander Black.
This role included developing the huge swathes of land around the city owned by the Heriot Trust, particularly in the West End of Edinburgh, and also building ten Heriot Trust Schools around the city for the less privileged children to attend.
His father William, mother Margaret Bell (d.1829), wife Ann Stennett (1827-1900) and numerous children (most of whom died young) lie with him.