Background and objective The prostate gland, which plays a crucial role in the male reproductive system, has a complex structure and function. Prostate enlargement, often benign but occasionally malignant, poses significant health concerns, particularly in aging populations. Prostate-specific antigen (PSA) serves as a vital biomarker, reflecting changes in prostate architecture and aiding diagnostic stratification. Elevated PSA levels correlate with prostate pathology and standard grading systems such asGleasongrading help guide treatment decisions. This study aimed to investigate the correlation between prostate enlargement, PSA levels, and Gleasongrades, particularly within the Indian context. Materials and methods This study was conducted over one and a half years at the Department of Pathology, Rajendra Institute of Medical Sciences, Ranchi, and involved 100 cases of clinically enlarged prostates. Clinical data, including age, symptoms, and relevant features, were collected, and histopathological analysis was performed on biopsy specimens. Statistical analysis was conducted using Microsoft Excel and SPSS Statisticsversion 20.0 (IBM Corp., Armonk, NY). Results Our study identified possible links between several factors and prostate conditions. Non-vegetarian diets showed a potential association with increased adenocarcinoma prevalence (p = 0.179). Urinary symptoms like hesitancy, incomplete voiding, retention, frequency, and urgency were significantly more common in men with adenocarcinoma (p<0.05). Additionally, bone pain and abnormal digital rectal examination (DRE) findings strongly correlated with adenocarcinoma (p<0.001). As expected, age showed a positive correlation with prostate weight and PSA levels (p<0.01). Interestingly, bone pain was associated with a lower likelihood of other prostate symptoms (p = 0.023). Conclusions Our findings provide key insights into the clinical factors associated with prostate pathology and highlight the need fora comprehensive approach to diagnosis in these patients, integrating clinical evaluation and histopathological assessment.