Despite the limited reliability of the documents that would confirm it, this monastery has been considered one of the oldest in the Principality. Its foundation is dated to the year 780, and it is attributed to Adelgaster, son of the Asturian king Silo. Leaving aside this tradition, it is known that during the 11th century, the site was occupied by a mixed community under the direction of abbots and abbesses.
Initially, it was a family-type monastery, influenced by patrons, one of which was the monastery of San Juan de Corias. The first reliable document of this monastic establishment dates from the year 1022, when its large patrimonial domain began to form, largely made up of donations from royalty. The last known abbess is documented in the year 1113, and from that point on, the community was restructured, freeing it from its family monastery status, leaving only monks and placing it under the rule of Saint Benedict. During this period, the Romanesque church that still stands was built. This period of prosperity lasted for the following centuries.
In the 15th century, the monastery suffered from the instability of the region, a situation that worsened with the arrival of commendatory abbots and the conflicts that culminated in the burning of the monastery. In 1536, the pope abolished the commendatory system, and in 1538 the monastery became part of the Congregation of San Benito de Valladolid. This new situation brought a period of stability, allowing for improvements in both the furnishings and the monastic dependencies. These renovations began in 1658 but were left unfinished.
In 1661, a college was established there, which in 1693 was moved to Santa María de Obarenes (Burgos), but was later restored. By the 19th century, the monastery had suffered the effects of the Peninsular War, the Liberal Triennium, and finally the disentailment of 1835. Currently, the parish church retains its function, now dedicated to San Antolín. It is a medieval building, dating to the 13th century, with later modifications, and it houses a 12th-century crucified Christ. The rest of the monastic buildings are in a state of abandonment, with the cloister dating from the 17th century, time of the reconstruction of much of the monastery.
- CABAL, Constantino (1950). El Monasterio de Obona. Boletín del Instituto de Estudios Asturianos, núm. 11
- GARCÍA ÁLVAREZ-BUSTO, Alejandro; ed. (2020). Asturias monástica. Catálogo de monasterios y revisión histórica arqueológica (siglos XI-XIX). Vol. 1. Anejos de Nailos n.º 7. Ovedo: KRK Ed.
- GARCÍA GUINEA, Miguel Ángel; dir. (2006). Enciclopedia del Románico en Asturias. Aguilar de Campoo. Fundación Santa María la Real
- MARTÍNEZ VEGA, Andrés (2011). Monasterios medievales de Asturias. Oviedo: Cajastur, 2011
- MENÉNDEZ GRANDA, Alfonso; i altres (2007). Intervención arqueológica en el Monasterio de Santa María la Real de Obona (Tineo). Excavaciones arqueológicas en Asturias 1999-02. Consejería de Cultura, Comunicación Social y Turismo
- SANZ FUENTES, María Josefa (1996). Documentación medieval del Monasterio de Santa María de Obona en el Archivo Histórico Diocesano de Oviedo. Asturiensia medievalia, núm. 8
- SANZ FUENTES, María Josefa (2002). Documentos medievales del Monasterio de Santa María de Obona en la Chancillería de Valladolid. Revista de filoloxía asturiana, núm. 2
- SANZ FUENTES, María Josefa; i altres (2002). El arquitecto Melchor de Velasco y el claustro del monasterio de Obona. De arte: revista de historia del arte, núm. 1
- YEPES, Antonio de (reed. 1959). Crónica General de la Orden de San Benito. Madrid: B. Autores Cristianos
- ZARAGOZA PASCUAL, Ernesto (1993). Abadologio del monasterio de santa María la Real de Obona (1511-1835). Boletín del Real Instituto de Estudios Asturianos, núm. 141