Palazzo Innamorati-Ciucci, now known as Simonetti, is a 15th-century residence that retains traces of even older structures, including 14th-century monoforas that were later bricked up. The facade, crafted from finely worked travertine blocks, reflects the building's prestige and the significance of the family who lived there for centuries, the Innamorati, one of the oldest and noblest families in Ascoli.

The connection to the Innamorati family is directly evidenced by the coat of arms painted in fresco on the vaulted ceiling of the ground floor room, depicting a rampant lion holding a flower, possibly a rose, in its jaws, which is now in need of restoration. This evidence is complemented by the wealth of surviving architectural elements: spacious vaulted rooms, travertine enclosures and corbels, and lintels inscribed with Latin phrases, creating a rich tapestry of historical allure.

The inscriptions above the doorways reveal a robust classical education and a profound ethical awareness. Particularly noteworthy is the maxim inspired by the verses from the first book of Horace's Satires, "nemo sua sorte contentus," suggesting that the inhabitants of this austere palace were educated and aware individuals, immersed in the humanistic thought of their time.

The palace was originally built as a prominent patrician residence, intended to accommodate a family of high rank and its descendants. The Innamorati family is documented as far back as the 14th century, with members taking on significant public roles beyond Ascoli, such as Filippo Innamorati, who served as captain of the people in Orvieto for several years, and Muzio Innamorati, who was the governor of the same city. During the 15th century, the family became involved in the complex political and social affairs of Ascoli; a Giovanni Innamorati is noted for writing a letter to the Florentine humanist Coluccio Salutati.

Particularly significant are the documents from the late 15th century, which mention Giovanni Innamorati and his son Pietro, who were granted the right to reside securely in the castle of Appignano. In 1483, Giovanni Innamorati also commissioned master Giacomo di Giorgio to create the parapet of a well, further testament to the family's economic stability and prestige.

In the 16th century, a Giovanni Battista Innamorati served as an ambassador in Naples to secure confirmation of tax immunity on wool fabrics, which were in high demand at fairs in Trani, Ortona, and Nocera. However, starting in the 17th century, the family, like many other noble families in Ascoli, faced gradual decline, leading to their downfall and eventual extinction at the beginning of the century.

From that point on, the palace began to undergo transformations and layers imposed by time, with numerous alterations that are now difficult to chronicle accurately. In the 19th century, thanks to meticulous land registry research, the figure of Carlo di Pietro Ciucci emerges, a documented owner in 1830, belonging to another noble family from Ascoli, originally from Quintodecimo, which had moved to the city in the 15th century.

The transition of the palace to the Ciucci family is confirmed by the presence of a more recent and less impressive coat of arms in scagliola on the eastern wall of the raised ground floor, compared to the ancient emblem of the Innamorati. A few years later, in 1832, the building was transferred to the bishopric: it was either purchased or, more likely, inherited by Bishop Gregorio Zelli Iacobuzzi of Ascoli, marking the final significant chapter in the long history of this centuries-old and majestic palace.