Keesmaat promised to tear down the eastern section of the aging and decaying Gardiner Expressway and replace it with a ground level boulevard, pointing out that cities all over North America are choosing to tear down urban expressways rather than spending hundreds of millions of dollars on maintaining outdated infrastructure. Keesmaat said the move would save the city roughly $500 million as opposed to re-building the decaying urban expressway, and that the decision would unlock "New communities with new jobs in retail and employment and affordable housing — places for people to live — by unlocking this land...This is really about creating a livable city. It's about creating a sustainable city. It's about creating a green city, and it is about moving Toronto into the 21st century", said Keesmaat. Keesmaat proposed a property tax increase on the sale of luxury homes to help pay for building 100,000 units of affordable housing. She also supports a municipal handgun ban. Keesmaat had pledged funding to double the number of emergency response mental health workers and to enhance community policing efforts by ensuring community police officers are assigned to every one of Toronto's 140 neighbourhoods. Keesmaat also unveiled detailed plans to enhance gender fairness in the Toronto municipal bureaucracy, support and promote the arts, improve transparency at municipal agencies, and build clean, green, and sustainable infrastructure. Keesmaat lives with her family near Yonge and Eglinton. She is married to Tom Freeman, who runs FH Hospitality, a Toronto-based sales firm that supplies fixtures and furniture to hotels. Together, Keesmaat and Freeman have two children, Alexandra and Luis.