Anne Redpath O.B.E. A.R.A. (British, 1895–1965)
Monastery of Santo Domingo el Real, Toledo

signed 'Anne Redpath' (lower left)
oil on board

Dimensions: 63.7 x 76.5 cm. (25 1/8 x 30 1/4 in.)

Elizabeth Ashley (1920-2001), 31 January 2001, whom bequeathed to the present owner

The Monastery of Santo Domingo el Real stands on the northern heights of Toledo’s old city, a short distance from the Puerta del Sol and the Monastery of Santo Domingo el Antiguo. Founded in 1364, it became the first Dominican convent for women in the city and enjoyed strong royal patronage; its title “el Real” (“the Royal”) reflects its association with the Castilian court. The architecture bears the marks of centuries of development: Gothic foundations interwoven with Mudéjar, Renaissance, and later Baroque interventions. Its robust stone and brick walls, modest openings, and square bell tower reflect the defensive yet spiritual character typical of Toledo’s monastic buildings. Set within the labyrinthine medieval streets and steep topography of Toledo, the monastery’s austere façade and enclosed courtyards evoke both seclusion and the layered religious history that defines the city.

“I am someone who is very interested in colour – and by that, I mean bright colour, gay colour; but at the same time, if you are a colourist, you like quiet colour as well and I think this love of gay colour is contrasted in my mind with this love of whites and greys.” - Anne Redpath

The Monastery of Santo Domingo el Real has long attracted artists drawn to Toledo’s textural architecture, shifting light, and spiritual atmosphere. From El Greco, whose nearby studio immortalised the city’s skyline, to later modern painters who responded to its tactile materiality. In this painting, Anne Redpath captures the monastery’s quiet dignity and tonal harmony, using thick impasto and subdued ochres to translate the weathered stone and reflected light of the square into a richly tactile surface. Redpath’s interpretation transforms architectural solidity into painterly rhythm: the rough plaster, muted walls, and sparse trees become vehicles for exploring the balance between structure and feeling. Like many 20th-century artists who found inspiration in Toledo’s timeless austerity, Redpath used the city not merely as a subject but as a means to explore texture, atmosphere, and spiritual presence through paint.