Novel terpolymers with furan and maleimide units as functional moieties for the reversible crosslinking by the Diels–Alder (DA) reaction with different polar and nonpolar co-monomers and linkers have been prepared for potential applications as self-healing coatings. The synthesized linear one-component systems are able to crosslink via the functional units in the side chain (i.e. furan and maleimide) resulting in a highly crosslinked network. The terpolymers contain different maleimide methacrylates with three different linkers (MIMA 1, MIMA 2, MIMA 3), which vary in the length and the composition of the spacer unit as well as furfuryl methacrylate (FMA) as active units. Moreover, as polar co-monomers hydroxyethyl methacrylate (HEMA), dimethylaminoethyl methacrylate (DMAEMA) as well as 2-(hydroxyethoxy)ethyl methacrylate (DEGMA) and as nonpolar co-monomer butyl methacrylate (BMA) were used. The terpolymers were characterized using 1H NMR spectroscopy and SEC measurements; the thermal properties were studied by TGA and DSC investigations as well as the self-healing properties by real-time analyses using a microscope equipped with a camera.