Background: This study aimed to investigate the fracture patterns and complexity of distal humerus fractures with high-resolution computed tomography (CT) as a function of Dual-Energy X-ray absorptiometry (DXA)-derived bone marrow density (BMD) measurements in an elderly patient cohort. Methods: A retrospective chart review was conducted on patient data collected at a Level I trauma center between January 2007 and January 2022. Inclusion criteria comprised patients aged ≥40 years with a confirmed distal humerus fracture as demonstrated by CT. Additionally, patients were included if they underwent DXA. Patient demographics and detailed information regarding the surgical treatment and trauma mechanism were retrieved from the institutional databank. Fractures were classified as either ‘low-plane’ distal humeral fractures or ‘non-low-plane’ distal humerus fractures. Furthermore, the fracture patterns were classified according to established classification systems. Intra- and postoperative complication and revision rates were analyzed. Results: A total of 41 patients (30 women; mean age 74 ± 13 years) were enrolled. Low-energy trauma was sustained by 68% of the patients. The remaining 32% of the fractures involved medium-energy trauma. A total of 62% of the patients underwent primary osteosynthesis, while 30% of patients were initially treated with an external fixator. ORIF was performed in 89% of cases and, in the majority, double-plate osteosynthesis was used (76%). An olecranon osteotomy was performed in 30% of cases. A total of 5% of cases received total elbow arthroplasty, and 10% of cases were treated conservatively. A total of 61% of patients had osteoporosis, 24% of patients had osteopenia, and 15% of patients had a normal BMD with an overall mean T-score of −2.4. Most of the fractures were complex (including 61% Type C fractures). A total of 66% of cases were considered as ‘low-plane’ fractures. Postoperative complications occurred in 11% of patients (64% of cases among ‘low-plane’ fractures). Revision surgery was required in 20% of cases. Conclusions: The consecutive series of patients showed a high incidence of ‘low-plane’ fractures. However, no statistical significance was found between the BMD and fracture complexity. The very distal ‘low-plane’ fractures showed a high complication rate, which was aggravated by osteoporotic bone conditions. These findings highlight the need for future research with larger patient samples to better understand the relationship between the BMD, fracture complexity, and outcomes in patients with ‘low-plane’ fractures in order to reduce complications and improve clinical outcomes.