Mr. Justice Robert Maxwell Dennistoun

Dennistoun House in winter ca. 1908. Image courtesy of the Provinical Archives of Manitoba and the City of Winnipeg Historical Report.

Colonel R.M. Dennistoun at Tidsworth Barracks, Salisbury Plain, England ca. 1915. Image courtesy of the City of Winnipeg Historical Report and the Provincial Archives of Manitoba.

The back of 166 Roslyn Road, ca. 1908. Image courtesy of the Provincial Archives of Manitoba and the City of Winnipeg Historical Report.

The House

The Dingwall Residence at 52 Roslyn Road ca. 1976. Image courtesy of the University of Manitoba's Winnipeg Building Index.

The front entrance to the Dingwall Residence at 52 Roslyn Road ca. 1976. Image courtesy of the University of Manitoba's Winnipeg Building Index.

166 Roslyn Road. Image courtesy of the City of Winnipeg Historical Report.

Dennistoun House, not long after its completion ca. 1908. Image courtesy of the Provincial Archives of Manitoba and the City of Winnipeg Historical Report.

"I'd be sad to see the old house go because it has some sentimental value,

but also because I like how the landscape of Osborne Village reflects

its history and its diversity" ~ Molly Johnson







"I think it is time Winnipeg got its act together and did not set up these "one or the other" scenarios. There are plenty of spaces to add density and housing downtown without sacrificing our culture and history. Great cities make room for both." ~ Suzanne Gessler



Article by Laura McKay, on behalf Heritage Winnipeg Corp.

To follow up on this or any other articles on the blog, contact Heritage Winnipeg's Executive Director.



News Articles

June 2, 2009 - Century-old home on Roslyn stripped of heritage status

June 2, 2009 - Winnipeg heritage building stripped of status, slated for destruction

June 5, 2009 - Why tear down a building dream?

June 10, 2009 - An Osborne heritage building by any other name...

June 10, 2009 - Century-old Winnipeg home a step closer to demolition

June 24, 2009 - City council strips 101-year-old Osborne Village home of its heritage status

Sept. 30, 2009 - Heritage battle goes to court

June 18, 2010 - Green light or no, condo sales begin

July 26, 2010 - Area residents lose appeal to save historic home

Sept. 8, 2015 - Osborne Village character homes could meet wrecking ball

Sept. 15, 2015 - Dennistoun House in Osborne Village at risk for demolition

Sources & Links

"166 Roslyn Road : Dennistown House " . Report prepared by the Historical Buildings Committee . 9 October 1984. Print.

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By 1880, Winnipeg's business leaders began to build new homes on land across the Red river in the southern portion of the city. The district came to be called Fort Rouge, after the fur trading post built in 1738 by LaVerendrye at the juncture of the Red and Assiniboine Rivers.By the early 1900s, the Winnipeg Electric Company had accelerated the growth of outlying suburban districts, providing wider streets and larger lots that only the affluent could afford. Roslyn Road, the first street south of the Osborne Bridge, became the district of stately bankers' homes.The house at 166 Roslyn Road was built in 1909 by Mr. Justice Robert Maxwell Dennistoun (sometimes spelt Dennistown), who at the time was a partner in Machray, Sharpe, and Dennistoun. Barristers and solicitors, these men kept offices in the Bank of Ottawa building at 363 Main Street.Dennistoun was born in 1864 in Petersborough, Ontario, the son of a lawyer and the daughter of a judge. Following in the family business, he graduated with a BA from Queen's University in 1885 and was called to the Ontario Bar in 1888. A specialist in corporate law, he would come to represent many influential companies throughout his career.In 1892, he married Mildred Louise Beck of Peterborough. They would go on to have five children together. Three sons - James, John, and Robert - were born in Ontario, followed by two daughters - Mildred and Mary - who were born in Manitoba.Dennistoun moved to Winnipeg in 1907 as the western counsel for the Canadian Bank of Commerce, later becoming the Bank's solicitor for Manitoba. That same year, he was called to the Manitoba Bar, followed by the Saskatchewan Bar in 1909. He was also honoured as King's Counsel in both Ontario and Manitoba, in 1908 and 1909, respectively.Among his many achievements, Dennistoun is known for drawing up Manitoba's first Workman's Compensation Act. He was also responsible for writing two monographs on military law, serving as the Governor of Trinity College in Port Hope, and lecturing in the University of Manitoba Law School of the day.In 1918, Dennistoun was appointed Puisne Judge of the Manitoba Court of Appeal, a position he held until he retired in 1946, at the age of 82. During this time, he was also made Deputy Judge of the Advocate General.Alongside his career as a lawyer and a judge, Dennistoun maintained a career in the military. He was a Major in the 57th Regiment of the Peterborough Rangers and went overseas in 1914-1919 (WWI) as a Colonel to the Canadian Expeditionary Force, for which he was later decorated. Having lost his son John in the Great War, he gave the dedication address when the bronze statue honouring the war dead was unveiled at the Legislature in 1923.Highly active in his community, Dennistoun was a member of the Masons (Corinthian Lodge No. 101), the Manitoba Club, the St. Charles Country Club, and All Saints Anglican Church. He also served as President of the Canadian Club of Winnipeg (1924-1925) and Commodore of the Royal Lake of the Woods Yacht Club. Lastly, he was a member of the first Advisory Board of the Winnipeg Foundation when it was founded in 1921.In 1923, the home at 166 Roslyn Road was sold and the family moved to 216 Cockburn House in Fort Rouge. Robert Maxwell Dennistoun passed away on October 10, 1952.After the Dennistoun family left, a widow named Mrs. Gertrude Stephen purchased the house and lived there until 1946, when it was purchased by restaurant proprietor Mrs. Myrtle Hall. Mrs. Hall stayed in the house until 1972, when it was purchased by the Richardson Company and likely used as temporary quarters for visiting and relocated company executives.Designed by architect John D. Atchison, 166 Roslyn Road cost approximately $15,000 to construct. The project's contractors were the Davidson Brothers. Atchison was the most important Chicago-style architect to work in Winnipeg, designing nearly 100 buildings between 1905 and 1922. Find a complete list of the buildings he designed here, on the MHS website 166 Roslyn Road is approximately 40 x 45 feet and has a dramatic, heavily detailed entrance. The exterior is made up of a combination of brick veneer, rough-cast plaster, and half-timbering, with limestone in the trim. The brick and rough-cast finishes contrast with the cross gables, making for a visually rich exterior.The building's entrance repeats the gable lines in light limestone that forms an archway. This, combines with the small panes of leaded glass in the door and side transoms to complete the old-world English look of the house. A two-storey brick balcony across the back of the house would have originally been screened in on the second floor, providing a sleeping porch - a popular feature in larger homes built prior to WWI.Dennistoun House is one of the strongest examples of Atchison's style from the period, with his mixing of finishes, emphasis on the front entrance, and the variation in the roof-line, which was usually accomplishes through gables and dormers. Dingwall House, built at 52 Roslyn Road, had a similar style but furthered the Scottish baronial look. This house has since been demolished and apartments built at that address.The writer of the original HBC report on this building asserts its importance to the Roslyn (and Osborne Village) district, as well as its importance as a historical connection to a notable figure in Manitoba's judicial and military history. Dennistoun House is also one the few private dwellings remaining from one of Winnipeg's early affluent suburbs, many of which have been lost to new development. It was these attributes, along with the historic exterior, that lead to Dennistoun House's municipal designation in 1984.In 2009, an application was made to have that designation removed. The Historical Buildings Committee advised against de-listing the building in a report issued on March 20, 2009. On June 2, 2009, the Standing Committee on Property and Development recommended the house be removed from the List. On June 24, 2009, Winnipeg's City Council accepted the Standing Committee's recommendation and 166 Roslyn Road was removed from Winnipeg's list of designated buildings.This de-listing was in direct contravention of the Osborne Village Neighbourhood Plan , which seeks to discourage the demolition of historic or architecturally significant buildings or structures. Demolition is only to be an option as a last resort, when buildings are found to be structurally unsound beyond repair by an independent structural engineering report (7.1.6.A on page 27).Heritage Winnipeg, concerned by the precedent being set for heritage buildings and older neighbourhoods in Winnipeg, advocated that the decision be reversed, along with the Osborne Village Neighbourhood Association and numerous members of the community. This eventually lead to OVNA, with support from Heritage Winniepg, taking the City to court on the matter, but unfortunately, they were unsuccessful in getting the decision reversed. The details of the Judge's Decision can be found here People both in the neighbourhood and the city at large had much to say about the de-listing and continue to object to the project. Below are some of the comments posted on the Planners Network Manitoba Website, shortly after the de-listing:At the moment, Dennistoun House is being used as apartments. The project continues to move forward and the building is set to be demolished to make way for a 12-storey condominium project, pictured above. For more details about the proposed condos, check out the development company's website . For more information about the delisting of this historic building and the ensuing controversy, check out the news articles and links below.