An exciting rediscovery awaits visitors to this year’s edition of the Winter Show, held at the Park Avenue Armory on Manhattan’s Upper East Side. Tucked in among the plethora of jewels, famous design objects, and antiques, is a rare 16th-century portrait by Sofonisba Anguissola, recognized as one of the greatest female Renaissance painters.

Portrait of a Canon Regular (1552), depicting a preacher with his raised hand resting on an open bible, is on view at the booth of veteran Old Master dealer Robert Simon who said it was unexpectedly discovered in a private collection in Durham, North Carolina, after experts believed it might be lost.

“Our canvas is one of fewer than 20 signed paintings by the artist,” Simon wrote in an essay accompanying the work. Over email, he told me that the painting had been known only through an old black-and-white photo at the Frick Art Reference Library.

Then in 2024, Michael Cole of Columbia University, who had written a “superb” monograph on the artist, delivered a lecture on Italian art at the National Gallery of Art in Washington, D.C. Titled “Sofonisba Anguissola: Recent Discoveries and Debates,” the lecture was broadcast on YouTube. The owners of the painting watched the talk and, knowing that the portrait they had inherited years ago was signed by Sofonisba, reached out to the professor.

“I was initially approached to value the painting and to consult on its conservation, provenance, and proper framing. In the end, the owners decided to sell the painting, and I am acting as their agent in bringing it to a wider audience,” Simon said.

Sofonisba Anguissola, Self-portrait (ca. 1535–1625). Collection of Łańcut Castle Museum, Poland.

Unlike other renowned woman artists of her day, Anguissola was not a child of a painter who was trained by her father. She came from a noble family in Cremona, Italy, and she and her sister, Elena, were trained by local painters Bernardino Campi and Bernardino Gatti. Sofonisba was regarded as the most talented of the seven children in her family. At a young age, she was known to both Michelangelo and Giorgio Vasari, who played a role in developing and promoting her skills as an artist.

According to Simon’s essay, in 1559, Sofonisba was summoned to Madrid, Spain, where she served as attendant to the Infanta Isabella as well as lady-in-waiting to Elisabeth of Valois, the Queen of Philip II.

Despite providing security and conferring social status on her, the royal appointment hampered her creativity due to the strict stylistic rules of the Spanish court. Thus, it is her early work in Italy—“her brilliant portraits of the 1550s,” as Simon noted—that are especially prized.

While the exact identity of the sitter in Portrait of a Canon Regular is not known, he can be “confidently” identified as a Canon Regular of the Lateran. This was an order of preachers related to the Dominicans, who followed the rule of Saint Augustine and had a significant presence in Cremona based in the monastery of San Pietro al Po.

Significant elements of the portrait include a Turkish carpet covering the sitter’s desk, “a preferred device of the artist that is found in several variations in her works,” as well as the legible text in the upper left corner with biblical passages in Latin from the Book of John, and an eagle, the symbol of Saint John, that grips the book with his talons.

According to the provenance listed for the work, it was last offered publicly at the Flying Eagle Auction Galleries in Durham, North Carolina on January 9, 1977, when it was acquired by the family who passed it down to the current heirs and owners.

The asking price is $450,000.

Sofonisba Anguissola, Portrait Of Joanna Of Austria (1547–78). Photo: Fine Art Images / Heritage Images / Getty Images.

The Artnet Price Database lists 120 results for Sofonisba Anguissola, though many of them are clearly labelled “Circle of,” “Follower of,” or “Attributed to.” The top auction price of £478,400 ($940,000) was paid at Christie’s London in December 2006, for Portrait of Margherita of Savoy in a white dress with gold and pink brocade, with flowers in her hair, standing next to a table with a King Charles Cavalier spaniel, which is labeled as “Circle of Sofonisba Anguissola.”

The second highest price, of €283,300 ($391,000), was paid at Dorotheum in Vienna in October 2011, for her portrait of Archduchess Johanna of Austria and is directly attributed to the artist.

The Winter Show is on view at Park Avenue Armory, 643 Park Ave, New York, through February 1.