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The church currently presents itself with the Neoclassical forms given to the building in the late eighteenth and early nineteenth centuries. It is an oriented building, that is, with the apse facing east, in the usual manner of medieval churches, so that the morning light, like the light of salvation could flood the church at every sunrise. The church turns its façade toward Tolomei Square with the wolfish column in the center, looking to the 13th-century palace bythe same name, to the right are Via di Calzoleria and Via CeccoAngiolieri, to the left Via Del Moro. Still as concerns the facade, we see it raised five steps above the current walking surface of the square; four circular brick pillars leaning against the wall support the entablature that echoes the motif of the ancient classical temple, the two elements are connected by the four white capitals, of a very sober workmanship. Above the entablature with alternating triglyphs opens the tympanum, also in bricks, with wide dentils, holding at its inside the marble effigy of the Tolomei family, namely the three crescent moons pointing upward, such as those standing out on the facade of the palace in front. Between the first two pillars in the niche is found the statue of St. Bernard Tolomei on the left that of Blessed Nera Tolomei. Before the statues were placed In these niches, they were occupied by two monumental vases, w replaced with sculptures in 1802. In the center of the facade, above the sober quadrangular portal with a ribbed tympanum, is the stained-glass window representing the Virgin, who is patron saint of the city of Siena, with the balzana at her feet and the words "SenaVetus, civitas Virginis"; this work was created in 1997 by Alberto Positano. Closing the tympanum is the cross above the three mounds, symbol of the Olivetan order to which the church is inextricably linked. The side walls on Via Angiolieri and Via del Moro present a juxtaposition of different materials in horizontal layers, bricks used for the reconstructions and stone probably coming from the original structure:these materialsare clearly visible in the entrance structure of the cloister on Via del Moro and outside the apse, again seen from the cloister. On the opposite side, a now closed door is still visible, framed in two piers of alternating colors. Internally, the church appears as a single-aisle building, not divided into naves, with a not too prominent transept and a small semicircular apse; it has three bays today, but was shortened during reconstruction to give more space to the square in front. The interior today appears soberly Neoclassical with plastered walls and vaults; prostyle pillars of circular cross-section with decorations of flowers and fruit on the capitals are connected by segmental arches of the same material. The only exception to this style is the part of the chancel with transept and apse, below the small tambour; these parts have exposed brick walls with the underlying band of stone, narrow single-lancet windows to illuminate the spaces, and wide round arches on antique-style capitals.
St. Bernard Tolomei: born with the name Giovanni to one of Siena's most powerful families in 1272, he undertook the study of jurisprudence, becoming a brilliant teacher and joining the confraternity of the Disciplinati di Santa Maria. Having gone through a deep religious crisis, in 1313 he withdrew with three other men to the desert of Accona in the hills to lead a hermit life, living in natural caves under the banner of poverty; here he changed his name to Bernardo, in honor of the Cistercian Bernard of Clairvaux. In 1319 at the behest of Guido Tarlati bishop of Arezzo, urged on by the Pope, he gave birth to the Benedictine congregation of St. Mary of Mount Olivet, of strong Marian devotion and with a reference to the Mount of Olives in Jerusalem. She died of the plague in 1348 in Siena and her body, thrown into a mass grave, was never found; according to other sources she was buried in the city monastery, which was destroyed centuries later.
Blessed Nera Tolomei: Born according to later sources in 1230 after an initial experience in the monastery of San Prospero she returned home to her Parents Iacopo Tolomei and Alessandra Malavolti. After attending one of the sermons of Blessed Ambrogio Sansedoni, a Dominican, she took a vow of chastity against the wishes of her mother, who wanted her married. Angered by her disobedience, Monna Alessandra locks her up in her room. There Nera has her first mystical and ecstatic experiences, which convince her mother to comply with her wishes; she will receive the habit as a Dominican tertiary precisely from Ambrose, whom she will follow in her preaching while taking care of the sick and pilgrims, especially women, welcomed into her home. Upon Ambrose's untimely death (1286), she is said to have witnessed his passing in ecstasy. She died in 1287 on Christmas Day and was buried in St. Dominic's next to Ambrose after two days of a huge influx of devotees that prevented an immediate funeral. Many miracles are testified even after her death, mostly miraculous healings.
To the left of the door: Epigraph of Count Claudio Tolomei: captain and deputy colonel of cavalry in the service of the emperor, he fought for twelve years in Hungary against the Turks. Recalled to Tuscany by Grand Duke Cosimo III he governed Grosseto and was in charge of the Poggibonsi arms depot. He died in 1720 at the age of 49. The epigraph is framed in a square marble slab with scrolling and plant-like decorations. The Tolomei family crestsurmounts a two-headedeagle.
To thr right of the door: Tomb of Nicola Incontri, Patrician from Volterra, upright auditor of the Sienese rota and Signora Flavia Bavestrellidei Conti Gallodori, his wife. Epigraph placed in 1748 by the then Bishop of Arezzo Carlo Filippo Incontri. Above the family coat of arms, two lions with a cross band
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