Background: The present study investigates comparative antioxidant, anticancer activity and qualitative, quantitative and spectral characterization of phytochemicals present among aqueous and ethanolic/hydro-ethanolic leave extracts of four medicinal plants viz. Anthocephalus cadamba, Aegle marmelos, Emblica officinalis and Moringa oleifera. Methods and Findings: In vitro antioxidant capacities were evaluated via free radical scavenging assays: DPPH, FRAP, ABTS, phosphomolybdate assay and total reducing capability. In vitro anticancer activity was evaluated against three human cancer cell lines SK-OV-3, A498 and T-24 by SRB assay. Quantitative estimation of phenolic, flavonoids, flavonols and Vitamin C content was done calorimetrically. Spectral characterization of phytochemicals was done via UV-Vis, FTIR and GC-HRMS analysis. Among all the leave extracts, aqueous and hydro-ethanolic leave extracts of E. officinalis has highest reducing power and lowest IC50 value for DPPH free radical with higher phenolic content. Evaluation of anticancer activity of leave extracts showed no significant activity against above cell lines. Spectral characterization of phytochemicals showed the presence of carbohydrates, carboxylic acid, phenols, flavonoid and Vitamins.