Harry Maidment was born in 1868 into a family of cabinet makers in Hoxton. His elder sister Ellen married landscape painter Octavius Thomas Clark. Harry's work is very similar in style and content to paintings by Octavius and his sons Stanley and Louis. Octavius is known to have taught his sons to paint and may have taught his brother-in-law too - Harry was only seven years older than Louis. Sometimes Harry painted under the name of R Fenson.
Harry is first noted as "artist" on the 1891 census, when he was aged 22 and living with his parents in Prebend Street, Islington. He married Alice Fisher Piggott in 1894 and they lived with their three children in Oxford Road (later renamed as Elizabeth Avenue), Cannonbury, Islington.
During World War II, Harry moved to Nottinghamshire, where he died in 1942 at the age of 74.