Background/Objectives: The Mediterranean diet has been widely suggested to exert significant beneficial effects on endothelial oxidative status and cardiometabolic health. Greek Orthodox monasteries, due to their specific nutritional and sartorial habits, comprise a population thatstrictly adheres to nutritional patterns with restricted eating and a plant-based subset of the Mediterranean diet, often accompanied by profound hypovitaminosis D. Time-restricted eating (TRE) is also adopted bya large part of the general lay Greek population for health-promoting reasons, without restrictions on animal product consumption, as imposed by Orthodox religious fasting. However, the comparative effects of these nutritional patterns on oxidative stress markers remain scarce. Methods: The present study attempted to evaluate the effects of Christian Orthodox fasting (COF) in a group of vitamin D-deficient and overweight Orthodox nuns from Central and Northern Greece compared to the implementation of TRE, a 16:8 dietary regimen (16 h of food abstinence and 8 h of feeding) in a cohort of adult women from the general population from the same region with regard to markers of endothelial oxidative status. A group of 50 women from two Orthodox monasteries in Northern Greece and one group of 50 healthy lay women were included. During the enrollment, a detailed recording of their dietary habits was performed, along with a scientific registry of their demographic and anthropometric characteristics (via bioimpedance). The Orthodox nuns followed a typical Orthodox fasting regimen [daily feeding window (8 a.m.–4 p.m.)], whereas the lay women followed a TRE 16:8 regimen with the same feeding time-window with a recommendation to follow a low-fat diet, without characteristics of the Mediterranean diet. We included a complete biochemical analysis, as well as calciotropic profiles [calcium—Ca, albumin, parathyroid hormone—PTH, and 25-hydroxyvitamin D—25(OH)D] and markers of TAC (total antioxidant capacity), GSH (glutathione),and thiobarbituric acid reactive substances (TBARSs) concentrations as markers of oxidative status. Results: All the groups were compared at the baseline regarding their calcium, PTH, and 25(OH)D concentrations, with no statistically significant differences between the groups apart from higher PTH levels in the nuns due to lower 25(OH)D levels. The Orthodox nuns manifested a lower median GSH compared to the controls (6.0 vs. 7.2, p 0.04) and a higher median TAC (0.92 vs. 0.77, p < 0.001). The TBARS comparisons showed no significant difference between the two groups. No significant associations of oxidative status with 25(OH)D, PTH, and the markers of glucose homeostasis were evident. Conclusions: The results of this small pilot study indicate that both dietary regimens have advantages over the oxidative markers compared to each other, with increased TAC in the group of Orthodox nuns after a 16-week period of COF compared to a 16:8 TRE and increased GSH concentrations in the lay women group. Future randomized trials are required to investigate the superiority or non-inferiority between these dietary patterns in the daily clinical setting.