In 1919, he interrupted his studies in the Fine Arts School of Porto (Escola Superior de Belas Artes do Porto), and resumed his education in Paris, where Cormon and Bérard were among his teachers.
Medina was an academic painter during Modernism, and his subsequent career as a portraitist had an international reach.
In his youth, Medina had spent vacations in his family's house in the suburbs of Marinhas, located in the municipality of Esposende. In 1974, at the age of 73 he returned to Esposende to live, and to paint portraits of rural life. Today, the secondary school of Esposende is named "Escola Secundária Henrique Medina" (Secondary School Henrique Medina) in his honour.