The property is on the southwest corner of the intersection of South Highland and Maple Place, across the former from Ossining High School and the latter from the brick 1870 First Presbyterian Church designed by Isaac G. Perry.

The house itself is a two-story, three-bay structure of 18-inch–thick (46 cm) load-bearing precast concrete blocks faced in stucco.

They have narrow round-arched one-over-one double-hung sash windows with stippled corners scored[5] to give the appearance of quoins serving as surrounds, becoming segmental arches with projecting keystones; a fleur-de-lys carved from Sing Sing marble is on the front stone.

The north wing has a wooden balustraded porch and arches as well; behind it are round-arched two-over-two double-hung sash in quoined surrounds.

On the entrance tower, the roofline is continued with a section of concrete laid to appear as a slightly projecting flat course.

The tower's roofline is broken by another double-hung two-over-two round-arched window flanked by mirroring brackets.

A successful New York City businessman who moved to Ossining,[5] he had an interest in construction, having initiated the effort to build a new Methodist church in town.

The local newspaper reported in March 1872 that he was going to build houses of "Swiss architecture" on his lots on Highland and Mott Street (as Maple Place was then known).

Their buyer, an elderly woman, lived there for a short time before selling in turn to a man named John Cockcroft.

In the years after World War I, Squire, a member of the state Naval Militia, used it as a hospital for injured sailors.

[2] During the 1920s Squire's public service continued, as the village's health officer and a county medical examiner.

When Dr. Squire assumed the medical examiner's position in 1925, his secretary needed to be able to accompany him on any emergency calls, so a basement apartment was constructed for the man and his wife to live there from 1936 to 1944.

She continued to teach office and secretarial skills there for 20 years, and tutored private pupils[2] until 1984.