An unprecedented [5 + 2] spirocyclization route to obtain a vital class of functionalized spirobenzo[b]oxepine-cyclopropanes in good to high yields with excellent diastereoselectivities is reported. This domino reaction proceeds through a regioselective oxa-Michael addition of ortho-hydroxyacetophenones as 1,5-binucleophiles to in situ produced highly reactive cyclopropenes from 2-aroyl-1-chlorocyclopropanecarboxylates triggered by Cs₂CO₃ and the subsequent intramolecular aldol reaction under heating conditions, enabling the formation of new C–O and C–C bonds for benzo[b]oxepine ring synthesis. Moreover, at ambient temperature, the above C–O/C–C bond-forming event takes place preferentially via a [4 + 2] annulation path over a spirocyclization route, leading to substituted fused-cyclopropanes with good diastereoselectivities. Gratifyingly, further alterations of the obtained spirobenzo[b]oxepines and tetrahydrocyclopropa[b]chromenes afford fascinating classes of 4H-chromen-4-ones and cyclopenta[c]chromenes, respectively, under metal-free conditions.