The health benefits of green space have led to calls for equitable access to parks. When new green spaces are built in low-income communities, however, gentrification often ensues. The “green gentrification” literature has paid little attention to gentrification that might occur before greening. In this paper, we explore whether and under which circumstances gentrification might precede and follow greening, a process known as the “green gentrification cycle.” Focusing on Los Angeles and Chicago, we build hedonic models focused on single-family homes sold in 2010–2021 and run post-hoc pairwise comparison tests to assess price changes over time for homes within a half-mile of new parks (treatment) and farther (control). When considering all new parks, we find that gentrification is associated with subsequent greening and, to some extent, that greening is associated with ensuing gentrification in Los Angeles. In Chicago, gentrification is associated with subsequent greening, but new parks are not associated with ensuing gentrification. Models distinguishing larger regional from smaller non-regional parks show evidence of gentrification before and after non-regional parks were built in Los Angeles, but not for regional parks. In Los Angeles, we identify stronger evidence of gentrification preceding greening farther from downtown than closer to downtown, and signals of gentrification after greening near downtown but not farther away. Models focusing on new parks built near transit stations show inconclusive results. Despite methodological limitations (e.g., examining a single measure of gentrification and different park types together), our findings shed light on the complex spatiotemporal relationships between greening and gentrification.