The origin of the areas name, are both related to the toponymy of Calheta (which means “small bay” in Portuguese): first, that there existed a small bay or cove, which already had this name, but secondly, that the area of the settlement was the off-port for sugar and collection of wood. Calheta was founded in 1430; the parish, of the same name (which is the central part of the municipality) is one of the oldest parishes on the island of Madeira, and one of the first to be explored by the early settlers. It was the area selected by João Gonçalves Zarco (the island’s discoverer) as a grant to his son and his wife, João Gonçalves da Câmara and Beatriz Gonçalves.
The village became a town 72 years after its foundation, on 1 July 1502, after a royal foral (charter) was granted by King Manuel I. The region was primarily settled by noblemen and knights, influencing the toponomic names that appeared in many of its localities: such as Lombo do Doutor and Lombo do Atouguia. In 1502, João de França constructed the Chapel of Nossa Senhora da Graça (English: Our Lady of Grace), which was to be the basis for the new parish of Calheta, founding the first and oldest institutions of the parish. Similarly, the Santa Casa da Misericórdia was established in 1535, to serve the elderly and provide healthcare for the local residents.
The parish of Prazeres, which was an ecclesiastical component of Estreito da Calheta was dismembered in 1733, becoming an autonomous clergy on 12 November (which was later followed by the first cornerstone of the Church of Prazeres, in 1751). The Liberal revolution resulted in the incorporation of Calheta as municipality in 1835. Similarly, the parish of Ponta do Pargo, after several years being part of the municipality of Porto Moniz (between 1835 and 1849), began to function as an administrative unit of the municipality of Calheta after the latter municipal seat was disincorporated. The restoration of Porto Moniz in 1855, resulted in the parishes reincorporation within the borders of Porto Moniz. By law, on 26 June 1871, was reintegrated into Ponta do Pargo.
Tristão Vaz Teixeira Bettencourt da Câmara, was granted the title of Baron of Jardim do Mar: his was a proprietor and later the director of the Diário de Notícias in Funchal. In one of the last events of the monarchy of Portugal affecting Calheta, King Carlos I of Portugal and Queen Amélie of Orléans visited the village of Calheta, travelling to Rabaçal, during their trip to Madeira. On 5 June 1922, the lighthouse in Ponta da Vigia, Ponta do Pargo was inaugurated to protect the western coast of the island.