Highland Cottage

Highland Cottage was erected in 1872 by Henry J. Banker, a wealthy and prominent social figure in the town of Ossining. “Baker had a strong interest in building as evidenced by his novel choice to build the house entirely of concrete. He also initiated the campaign to erect a Methodist church in the town and was a generous benefactor”.[1] In 1881 when Henry J. Banker died, the house was sold to Andrew and Jane Dickey who gave the house the name of “Highland Cottage”[2]. Th house was not in their possession for very long, and in 1887 it was sold to Emma Richards. Shortly thereafter in 1888, it was sold to John Cockcroft who would own the residence until 1905. In 1905, he sold the house to Dr. Amos Squire whose name is now associated with the house. 

Dr. Squire was born in Cold Spring, New York. His family immigrated to America in 1632. He received his higher education at the College of Physicians and Surgeons of Columbia University, Class of 1899. Later that year, he opened a private practice in Ossining. Dr. Squire utilized the house to run a private hospital called Grandview Sanitarium, while he and his family lived upstairs. In addition, Dr. Squire was appointed chief physician at Sing Sing Prison. Highland Cottage was transformed into a naval hospital during the first World War between 1917 and 1919. In 1920, it serves as a restaurant called the “Castle Inn” until 1923. The Squire family continued to occupy the top floor.[3]When the restaurant moved out, the Squire family reclaimed the house.

In 1925, Dr. Squire became the coroner of Westchester County, a post he held for six years.[4] He continued to pursue his interest in criminology and criminal minds. He gave lectures and presentations on the topic and authored a book called Sing Sing Doctor which was sold globally. Dr. Squire died in 1948, and the house was left to his daughter Evelyn Squire Culp.

Evelyn Squire Culp graduated from Columbia University School of Business and then received her L.L.B from St. Lawrence University in Canton New York. She practiced law in New York City and from 1941-52; she also taught finance and law at Briarcliff Junior College.[5] in 1952. She later used the Highland Cottage to privately teach business from her home until 1972.

The Highland cottage was a building that architecturally was ahead of its time as one of four concrete nineteenth century structures in Westchester. It is the only one of the nineteenth century structures to retain its original use as a residence. 

[1] Karen Kennedy, “Highland Cottage”, National Register of Historic Places Inventory—Nomination Form, July 22, 1982. 

[2] Ibid.

[3] Kennedy, 2. 

[4] Thomas Scharf, History of Westchester County (Philidelphia: L.E. Preston & Co., 1886), 332. 

[5] Kennedy, 3. 

Fitch, James Marston. American Building. Chicago: University of Chicago Press, 1969.