Background The feasibility of valve‐in‐valve transcatheter aortic valve replacement (ViV‐TAVR) after surgical aortic valve replacement (SAVR) and the impact of aortic root enlargement (ARE) remain unclear. This study assesses the anatomical feasibility of Viv TAVR post‐SAVR, with and without ARE through detailed pre‐ and postoperative gated CT scans. Methods We analyzed 62 patients undergoing SAVR ( n = 31) or SAVR + ARE ( n = 31) between September 2022 and May 2024. Pre‐ and postoperative gated CT scans were used to measure annular area, sinus of Valsalva (SOV) dimensions, coronary heights, and virtual valve‐to‐coronary (VTC) and valve‐to‐sinotubular junction (VTSTJ) distances. High‐risk ViV‐TAVR anatomy was defined as VTC < 4 mm or VTSTJ < 2 mm. Four enlargement techniques were used (Y‐Incision, Manouguian, Nicks and replacement of the coronary sinus). Results Female patients were more prevalent in the SAVR + ARE group (61% vs. 19.4%, p < 0.001). Preoperatively and compared to the SAVR cohort, SAVR + ARE had a smaller annular area‐derived diameter (23 ± 2 mm vs. 26.8 ± 2.2 mm, p < 0.001) and SOV dimensions (28.8 ± 2 vs. 32.8 ± 3.6, p ≤ 0.001) and, both cohorts had coronary heights of ≥ 14 mm. Postoperatively, both groups had a significant reduction in coronary heights by at least 7–9 mm ( p < 0.001). On the contrary, the SOV dimension increased significantly by +3 mm in the SAVR + ARE group (< 0.001), while it decreased numerically in the SAVR‐only cohort (0.07). Similarly, the majority of both groups were considered low risk for future ViV TAVR (SAVR: 24/31, 74%) and (SAVR + ARE: 22/31, 71%), while 22.6% (7/31) of SAVR and 29% (9/31) of SAVR + ARE were considered anatomically high risk. Conclusion While most patients who had SAVR, with or without ARE, were anatomically feasible for ViV TAVR, postoperative CT scans identified high‐risk anatomy in approximately 25% of cases. Pre‐ and post‐SAVR CT imaging offers insights into surgical planning and lifetime management of aortic valve disease.