Benedictine Nuns first inhabited the building complex, relocating from their original home in Cozzano to the relative safety found within the ancient walls along Via Piana, originally a crossroad of major urbanistic importance in the development of Castiglion Fiorentino in the 13th century. Remnants of this first monastic centre are still visible which include a balcony characterised by pointed arches and oval window overlooking a vegetable garden.

The 15th century (1470) witnessed the expansion of the Convent and the construction of a new church positioned along the road which was documented as measuring ‘thirty arms in length’.

In 1551 the Nuns obtained permission to open an entrance in the walls in order to extract earth from the gardens and build cellars. Sixteen buildings situated at Monte di Via Piana were bought to fulfil the requirement for extra space. These were later demolished in order to position the first stone of the new Convent completed in 1697 connecting the Via Piana by a bridge.

Unfortunately, a fire in 1707 seriously damaged the structures, resulting in the death of a nun and a partial collapse of the Church and of the adjacent part of the Convent. The scripture archive was also sadly lost. Restoration work completed the reconstruction of the last three levels and the adjacent Church which was re-modernised with stucco decoration.

The Order of the Santucce was ordered to close in 1810 and the complex became privately owned, used as residences divided into apartments.

The bombardment of Castiglion Fiorentino during the Second World War (1943) was extensive and many buildings suffered damage, including the convent which was partially destroyed. The gradual but intensive labour of love embarked upon to realise its reconstruction began in 1997 and was completed a decade later in 2007. Alfeo, who is an engineer by profession, has personally overseen every aspect of the work which includes an ample art studio space presided over by his talented wife Miranda.