We establish a general theoretical framework for realizing topological edge states in dimerized arrays of chiral dipolar molecules. The topological mechanism is that of the standard Su–Schrieffer–Heeger (SSH) model: the bond dimerization $\delta r$ controls the winding number and the bulk–boundary correspondence. Molecular chirality contributes in two ways absent in conventional achiral implementations. First, the Dzyaloshinskii–Moriya interaction generated by molecular handedness amplifies the effective hopping scale from $|J_{xy}|$ to ${\tilde{J}}_{xy}=\sqrt{J_{xy}^2+D^2}$, enlarging the bulk topological gap. Second, because the two sublattices of the dimerized array carry opposite molecular handedness, the two boundary modes inherit a stereochemical identity: the left edge state localizes on a left-handed molecule and the right edge state on a right-handed molecule. This chiroptical addressability of the boundary modes has no analogue in conventional achiral SSH chains. Starting from an effective spin-$\frac{1}{2}$ model for Stark-dressed chiral molecules, we introduce bond dimerization and map the system via a gauge rotation and Jordan–Wigner transformation to an interacting SSH-type fermionic chain treated in self-consistent Hartree–Fock. We benchmark the mean-field treatment against density-matrix renormalization group (DMRG) calculations for systems up to $N=200$ sites, finding that the self-consistent bond orders agree with their DMRG values to within 1.5%. We map out the trivial, critical, and topological regimes through bulk spectra, complex-plane winding, and boundary-localized probability densities. The two-leg ladder extension supports a richer four-band bulk structure and a rung-split edge sector. All results are expressed in dimensionless units of the reference hopping scale $t_0$, making the framework applicable to any dipolar molecular platform.