Many municipalities are working to protect and grow their urban forest, including adopting private tree regulations. Such regulations typically require property-owners to apply for a permit to remove trees and, if the permit is granted, plant replacement trees. Even with such regulations, many private trees are removed each year, particularly on residential property. Property-level construction activity, including expanding building footprints, replacing an older home with a new one, and increasing hardscaping, is emerging as a key driver of residential tree loss. This study addresses whether homeowners who receive a permit to remove one or more trees comply with the requirement to plant replacement trees to better understand the effect of private tree regulation. We explore this question through a written survey of homeowners who received a tree removal permit and site visits in Toronto (Ontario, Canada). While 70% of all survey participants planted the required replacement trees 2 to 3 years after receiving the permit, only 54% of homeowners whose permit was associated with construction planted. Additionally, most replacement trees were in good health but were dominated by a few genera. We also found significant differences in replacement planting and tree survival across the city’s 4 management districts. This study highlights that if resources supporting private tree regulations are limited, tree permits associated with construction should be prioritized for follow-up. Additionally, guidance about diverse species to plant should be communicated to ensure that private tree regulations are supporting the long-term protection of the urban forest.