This chapter describes recent synthetic advances and cutting-edge applications of dendritic polyesters. We present the synthetic evolution from traditional approaches to new chemistries, which translate to a large library of structurally diverse dendritic materials including monodisperse dendrimers and dendrons, linear-dendritic and surface-dendritic hybrids, and larger dendritic assemblies. Within each sub-family, various elegant approaches have been detailed in which click chemistry plays a fundamental role in overcoming existing challenges in the synthesis of advanced and monodisperse dendritic polymers. This includes orthogonal and accelerated growth to dendrimers with sequence-controlled linkages, heterofunctional dendrimers with precise representation of the functional groups displayed at the exterior and interior of the skeleton and dendritic hybrids that take advantage of the intrinsic properties of both blocks. Dendritic polyesters based on 2,2-bis(hydroxymethyl)propanoic acid (bis-MPA), as the main AB2 monomer building block, are one of the most dominant families today, being biocompatible, biodegradable and commercially available, thereof represented extensively in this chapter. Additionally, a detailed overview of reported building blocks is included, aiming to address current challenges through chemical modification of the monomer or the hybridization with other synthons. Structural perfection, characterization techniques and innovative applications are thoroughly discussed to give the readers an overall picture of the landscape presented in the literature.