Paget’s disease of bone (PD) and Charcot neuroarthropathy (CN) are rare conditions involving osteoclast activation and increased bone turnover. PD commonly affects the tibia, while CN affects foot bones. Though PD and skeletal metastases from breast carcinoma have co-occurred, the simultaneous presence of PD, CN, and skeletal metastases from breast carcinoma is unprecedented. A middle-aged female with type 2 diabetes presented with symptoms of pain, swelling, and inflammation in the right leg and foot. Diagnostic imaging suggested PD and acute CN. Despite treatment with zoledronic acid, there was no improvement. Later, she developed firm skin lesions and a breast lump, diagnosed as breast carcinoma with cutaneous metastasis. Chemotherapy, radiotherapy, and monthly zoledronic acid were administered. Follow-up imaging showed reduced tibial lesions but persistent skeletal metastases. This case underscores the complexities in diagnosis and management of patients with these concurrent conditions and highlights the need for thorough examination when standard therapies fail.