A three‐component, solvent‐dependent, Brønsted‐acid‐catalyzed reaction of benzaldehydes, silyl enolates and arene nucleophiles has been developed for the synthesis of potential drug candidate 3‐aryl‐1‐indanones. This reaction features the formation of three C−C bonds, high regioselectivity in a one‐pot strategy, broad substrate generality, facile scalability (1.04g), high functional group tolerance and viable substrates. The β‐O‐silyl ethers generated in‐situ from the Mukaiyama aldol reaction were subjected to acid‐catalyzed benzylic arylation with strong as well as weak nucleophiles, and the resultant β,β‐diaryl esters can undergo a third C−C bond formation with excellent regioselectivity through intramolecular cyclization to afford the indanone products in the same pot. Detailed mechanistic insight leads to a feasible reaction pathway. This transformation opens up a practical and adaptable approach to producing a variety of synthetically valuable transformations and enable the synthesis of medicinally valuable (R)‐tolterodine and (+)‐indatraline.