Urban green space (UGS) is increasingly recognized as a nature-based solution to achieving urban sustainable development. Under rapid urbanization, greening policies are often the main driving factor behind the restoration or even growth of UGS. In this study, Chengdu, the pioneering “park city” in China, is chosen as a representative region. Based on land use/land cover (LULC) and normalized difference vegetation index (NDVI) data, indicators that can reflect both UGS quantity and quality are constructed and the spatio-temporal characteristics of UGS in original and expanding urban areas are also explored at different greening policy stages. The findings show that, from 2000 to 2022, the basic trend of UGS reduction during urbanization remained unchanged, despite the greening policies implemented in Chengdu. However, the original urban area has evolved into a new urban area. This has been achieved by integrating the expanded urban area with higher greening rates, resulting in the greening rate in 2022 (44.61%) being restored to the 2000 level (44.21%). The implementation of green policies in Chengdu is primarily reflected in improved UGS quality, especially in the stage of the ecological garden city construction (2008–2018). Specifically, the UGS quality in the original urban area has been improved by 25.25%. Overall, the UGS quality in Chengdu Urban Center has improved, changing from a medium level in 2000 to a medium-high level in 2022. The construction of a national demonstration zone of the park city provides an opportunity for the UGS quantity to increase and quality to improve in Chengdu in the future. However, effectively considering the development positioning of the Tianfu Granary to coordinate the relationship between UGS and high-quality farmland is a huge challenge for urban sustainable development in Chengdu.