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The lot occupied by Rosemount was originally the property of Dr. N. D. G. Parker, the son of the Hon. Neville Parker, Master of the Rolls, who lived in the old Frye house at the corner of King and Montague, a house which devolved to his son and seems later to have been named "Cassa Rossa" and occasionally rented out to summer people by Dr. Parker. Dr. Parker, who was the possessor of many properties in St. Andrews, many of which sold to the newly formed St. Andrews Land Company in 1888, had built a beautiful home on this lot in 1879. The Pilot supplied a very detailed account of its structure and declared it one of the most beautiful homes in St. Andrews. The house however did not last long. Just when it burned is not known but when Charles Smith purchased the land in 1907 with the intention of erecting his own dwelling, it was noted that the Parker house had disappeared "many years ago."
1907 saw the construction of Rosemount, on Prince of Wales Streets, next to Hillcrest and Fort Tipperary. The owner was Mr. Charles F. Smith, of Montreal. The St. Andrews Beacon reported thus: "Charles F. Smith, who has recently become a permanent summer resident, is president of the James McCready Shoe Company, Ltd., of Montreal, a director of the Merchants' Bank, of the Laurentide Paper Co., and of other mammoth corporations. He is a man of charming personality and a welcome addition to the cottage population of St. Andrews." The architects were Edward and W. S. Maxwell, also of Montreal, and already the architects of various elegant summer homes for Montreal vacationers.
Mr. Smith remembered St. Andrews from his brief visit to the Town in January, 1862, when he along with a contingent of troops were being rushed to Canada in the diplomatic crisis since called the Trent Affair. During the Civil War a Union gunship seized two Confederate diplomatics from a British vessell on their way to Great Britain to press the case for British recognition of the Confederate Cause.
In 1912 the St. Andrews Beacon printed an interesting recollection of the role St. Andrews played in the event drawing from the diary of a local resident.