The development of high-performance recyclable polymers represents a circular plastics economy to address the urgent issues of plastic sustainability. Herein, we design a series of biobased seven-membered-ring esters containing aromatic and aliphatic moieties. Ring-opening polymerization studies showed that they readily polymerize with excellent activity (TOF up to 2.1 × 10⁵ h^–1) at room temperature and produce polymers with high molecular weight (M_n up to 438 kg/mol). The variety of functionalities allows us to investigate the substitution effect on polymerizability/recyclability of monomers and properties of polymers (such as T_gs from −1 to 79 °C). Remarkably, a stereocomplexed P(M2) exhibited significantly increased T_m and crystallization rate. More importantly, product P(M)s were capable of depolymerizing into their monomers in solution or bulk with high efficiency, thus establishing their circular life cycle.