Introduction/Objective: Venous Leg Ulcers (VLU) present a challenging healing process. Attaining healing is a primary treatment objective, commonly pursued in Primary Health Care (PHC) or Specialist Wound Management Clinics. Our objective was to examine the association and interplay between sociodemographic, health, clinical, and care factors with the outcomes of VLU treatment in patients undergoing care at a Specialist Wound Management Clinic. Methods: Longitudinal, observational study took place in a center for the treatment of chronic injuries linked to PHC. The sociodemographic aspects, health status and habits, clinical and care aspects of patients with VLU were scrutinized over a 1-year period. Results: The sample comprised 103 participants, with some still under treatment (Treatment Group—TG/ n = 60) and others having achieved VLU healing (Healing Group—HG/ n = 43). An association between sociodemographic, health, clinical, and care factors and the healing outcome (HG) was identified. A moderate correlation was observed between factors predisposing to healing in the sociodemographic group and health habits. Notably, among sociodemographic factors, the older age group and improvements in health, particularly the reduced use of alcohol/smoking, appeared to exert the most significant influence on healing. Additionally, specialized service monitoring and the application of compression therapy were contributory factors. Conclusions: These findings substantiate the hypothesis that sociodemographic, health, clinical, and care-related aspects are intertwined with VLU healing. Protective factors associated with healing interacted synergistically, fostering a positive outcome over one year of treatment.