The knowledge of polycystic ovary syndrome (PCOS) natural history is limited. Our objective was to assess the effect of aging on clinical, hormonal and sonographic ovarian PCOS features and additionally to identify parameters that impact the course of PCOS. A secondary aim was to supply additional information on the reproductive outcome in women with previously diagnosed PCOS. A longitudinal cohort study with a median follow-up of 120.9 months was conducted, and 31 Caucasian women previously diagnosed with PCOS according to the Rotterdam criteria were re-examined at a median age of 35. Clinical examinations; transvaginal ultrasound scans; and lipid, E-selectin and sex hormone assessments were performed at the beginning and at the end of the follow-up. It was observed that menstrual cycles became regular and sonographic morphology of ovaries was normalized in 55% and 49% of the participants, respectively (all p < 0.05). At the final assessment, 55% of the women no longer met the criteria for PCOS (p < 0.05). The age, follicle-stimulating hormone (FSH) and E-selectin assessed at the baseline were the most important predictors of the PCOS persistence into later years (respectively, OR = 0.84, OR = 0.39, OR = 1.08, all p < 0.05). Ninety-five percent of the patients who had ever been trying to conceive became pregnant a minimum of once. The women with persistent PCOS had worse metabolic and reproductive parameters compared to the women with resolved PCOS. Positive correlations were found between the number of miscarriages and ovarian volume, LH, androstenedione, 17-hydroxyprogesterone and an increase in E-selectin during the follow-up (R = 0.46, R = 0.59, R = 0.54, R = 0.49, R = 0.47, all p < 0.05). In conclusion, progressing from the third to the fourth decade is connected with a reduction in PCOS features, which seems to have a great impact on fertility of women with a previous diagnosis of PCOS. FSH and E-selectin, as determined at the initial PCOS diagnosis, had an impact on the disappearance of the syndrome years after.