Communities evolve and adapt to change to address the growing urban challenges such as urbanization, environmental sustainability, and social equity. These changes occur in response to the global diversity of needs, especially in urban areas that have rapidly become a melting pot. Cities like Calgary and Kumasi have grown and diversified from primitive beginnings to modernity over the past century. Calgary’s growth was driven by its fundamental role in the oil and gas industry. Kumasi’s growth was due to the cocoa boom and the influence of colonial planning policies. They were shaped by the dynamics in urban planning policies, land use regulations, and variations in socioeconomic arrangements manifested in the available housing forms/types and sizes. Early Calgary’s houses were modest single-detached, while Kumasi’s structures were characterized by traditional compound houses of more than fifteen rooms. Homes in both cities have modernized with modern building materials that respond to the population's needs. However, studies on why and how houses change over time are limited. Adopting the historical and archival research approach and relying on secondary data, the study explores how land use regulations and socioeconomic arrangements have influenced the transformation of these housing structures in both cities over the past century. The study found that while household size shrinks and income increases, people demand larger homes with attached car garages, large backyards, two-storey single-family detached homes, and other ancillary buildings in Calgary. However, in Kumasi, while household size shrinks, people shift their tastes and preferences to single-family homes built on smaller lots, consequently reducing the number of people they can accommodate, gradually creating a housing shortage and affordability issues. The study also found that residential zoning bylaws have significantly contributed to the transformation of houses in Calgary but are less effective in Kumasi. Due to how housing is supplied in Kumasi, housing transformation is driven substantially by the influence of foreign cultures, increased household income, and the shrinking household size. The findings would inform future housing interventions to address the growing population's needs.