Bounded by Wellesley, Howard, Sherbourne and Parliament Streets, the houses in St. James Town were some of the oldest middle-class homes in Toronto. Over the first half of the 20th century, however, wealthier residents began to move further north and were replaced by working-class and new immigrants who moved into converted rooming houses. In spite of this shift in the character of the neighbourhood many of the housing units were still of good quality.

In the mid-1950s St. James Town became attractive to private developers after the city amended its density bylaws for the area, authorizing a density far above anywhere else in the city. In 1956 a group known as the Parliament Syndicate assembled enough finances to build a series of 19 high-rise towers in St. James Town with 4,100 units and began to buy up houses to demolish them. After acquiring 70% of the property the Syndicate turned to the city government planning board, asking if they could use urban renewal law to expropriate (force people out of their homes) the rest. The planning board, however, refused the Syndicate's request and a strong and organized opposition emerged from local residents and their local MP Bill Dennison.

Opposition to the project complicated the Syndicate's grand plans for St. James Town but private companies, nevertheless, began to build high-rises in the high density area. By the mid-sixties this intensive building and the block-busting techniques of private developers caused the neighbourhood to deteriorate further. By 1965 a second group, Meridien, launched a renewed attempt to turn the area into private high-rises. This time the planning board were more enthusiastic and they met with diminished local resistance. Meridien was able to buy up the remaining properties by actively making the neighbourhood unliveable for local residents. In the late 1960s Meridian began to build their high-rise towers and over the 1970s continued to expand, building apartments for predominantly single people who worked in the downtown core.

Today, St. James Town is an extremely dense and diverse community. It is also home to many community oriented businesses and organizations but has, ironically, once again become the target of criticism by urban planners and critics. Part of this criticism has to do with deteriorating housing conditions, but high-rise housing has also become unpopular with Toronto planners who often associate it with a lack of community.

Kevin Brushett, "Blots on the Face of the City: The Politics of Slum Housing and Urban Renewal in Toronto 1940-1970" (PhD diss., Queen's University, 2001)

Steve Barnes, "Canada's Densest Neighbourhood, St. Jamestown, to possibly get new Condos," Wellesley Institute (2011), http://www.wellesleyinstitute.com/housing/st-james-town-residents-feel-powerless-in-light-of-new-development-in-one-of-north-americas-densest-neighbourhoods/