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High-density polyethylene (HDPE) is a widely used commercial plastic due to its excellent mechanical properties, chemical resistance, and water vapor barrier properties. However, less than 10% of HDPE is mechanically recycled, and the chemical recycling of HDPE is challenging due to the inherent strength of the carbon–carbon backbone bonds. Here, we report chemically recyclable linear and branched HDPE with sparse backbone ester groups synthesized from the transesterification of telechelic polyethylene macromonomers. Stoichiometrically self-balanced telechelic polyethylenes underwent transesterification polymerization to produce the PE-ester samples with high number-average molar masses of up to 111 kg/mol. Moreover, the transesterification polymerization of the telechelic polyethylenes and the multifunctional diethyl 5-(hydroxymethyl)isophthalate generated branched PE-esters. Thermal and mechanical properties of the PE-esters were comparable to those of commercial HDPE and tunable through control of the ester content in the backbone. In addition, branched PE-esters showed higher levels of melt strain hardening compared with linear versions. The PE-ester was depolymerized into telechelic macromonomers through straightforward methanolysis, and the resulting macromonomers could be effectively repolymerized to generate a high molar mass recycled PE-ester sample. This is a new and promising method for synthesizing and recycling high-molar-mass linear and branched PE-esters, which are competitive with HDPE and have easily tailorable properties.