A separar a Praia Grande da antiga Baía da Angrinha, o Castelo de São João de Arade é uma edificação erguida em cima de um rochedo, no reinado de D .João II ( séc. XV), provavelmente de vigia e defesa da barra de Silves, posteriormente fortificado no séc. XVII.  O terramoto em 1755 provocou inúmeros danos tendo sido restaurado no reinado de D. Maria I. Chegou a servir para controlo de tráfego das embarcações, mas em 1896 foi preterido nas suas funções sendo desartilhado, desguarnecido e posteriormente desclassificado militarmente. Foi vendido em hasta pública por 600$000 réis.

Nos finais do séc. XIX, sob evocação de S. João Baptista, foi salão literário. Nos inícios do séc. XX o Poeta Joaquim Coelho de Carvalho adaptou-o a residência, mas apesar das obras manteve o baluarte artilhado em distintos planos para canhoeiras de fogo alto e rasante.  É imóvel classificado desde 1974 e, depois de pertencer ao ex-ministro Francisco Vieira Machado, foi adquirido pelo atual proprietário.

Separating Praia Grande and the old Baía da Angrinha, the Castle of São João de Arade was built atop a rock during the reign of D. João II (fifteenth century). It probably served as a lookout point and defensive structure for Silves harbour and was later fortified in the seventeenth century. Having been severely damaged by the 1755 earthquake, it was restored during the reign of D. Maria I. The building was also used to monitor the traffic of ships. However, in 1896 the artillery was removed, and it was demilitarized and subsequently decommissioned. It was sold at public auction for the sum of 600,000 réis (a former Portuguese currency).

In the late nineteenth century, under evocation of Saint John the Baptist, it was used as a literary salon. In the early twentieth century, poet Joaquim Coelho de Carvalho converted it for use as a dwelling. However, he kept the battlements, crenellated at different levels for high and low cannon fire. The building has been classified since 1974 and was purchased by its current owner after having belonged to former Minister for the Portuguese Colonies, Francisco Vieira Machado.