Background: We assessed the real-life clinical impact of bone health management in patients with breast cancer (BC) receiving adjuvant endocrine therapy at an Italian Osteoncology Center. Methods: Pre- and post-menopausal women undergoing adjuvant endocrine therapy for early-stage BC who came to our institute for their first bone health evaluation from January 2011 to June 2016 were considered in this retrospective observational study. Results: 1125 pre- and post-menopausal early-stage BC patients (209 and 916, respectively) were evaluated. Median age was 61 years (range 26–88). In the pre-menopausal group, spinal x-ray revealed that 10 patients (4.7%) had a morphometric vertebral fracture. Higher age (OR: 1.14; 95% CI: 1.01–1.29) and bone mineral density (BMD) ≤ −2.5 (OR: 14.45; 95% CI: 1.70–122.67) were associated with a higher risk of bone fracture. The overall frequency of bone fracture was 17.6% (n = 161) in post-menopausal patients and a lower risk for bone fractures was associated with tamoxifen or other treatments (OR: 0.25; 95% CI: 0.12–0.53), presence of back pain (OR: 1.65; 95% CI: 1.16–2.36), lower BMD (OR: 2.09 in patients with T-score ≤ 2.5; 95% CI: 1.21–3.59) and lower vitamin D levels (OR: 1.57 in patients with ≤ 10 ng/mL; 95% CI: 1.05–2.34) in univariate analysis. Conclusion: Our findings confirm that bone health management should be an integral part of long-term cancer care.