The history of Santarella dates back to 1739, when the town of Tyringham, Massachusetts was settled. Shortly after, the colonial home was built on the site. Its most famous resident was Sir Henry Hudson Kitson, the English sculptor who is known for the Lexington Minuteman and Plymouth Rock Maiden statues in Massachusetts, as well as a number of Civil War bas-reliefs and sculptures in Vicksburg, Mississippi.

Henry Hudson Kitson Kitson met and eventually married Marie Hobron, daughter of Benjamin Hobron and a well-liked woman in Tyringham. Around 1920, Kitson began his work transforming the barn on the property into a sculpting studio where he could work. It was this project which eventually became Kitson's primary focus for the last 25 years of his life, and which consumed the remains of his earnings until he died a penniless man in 1947. He was knighted for his work in Rumania, and remains an important figure in American Scultping.