Enchondromas are frequently occurring cartilaginous tumors, accounting for 10-25% of all benign bone neoplasms. We present a distinctive case involving distal clubbing of the right third toenail with a painless, 5mm-wide red longitudinal streak. Clinical examination, nail matrix biopsy, and imaging confirmed the presence of an enchondroma in the distal phalanx. Although solitary enchondromas often present with pain or pathological fractures, asymptomatic cases like this one are quite rare. Given the low risk of malignant transformation, the patient chose regular magnetic resonance imaging (MRI) monitoring. This case highlights the need to consider enchondromas in the differential diagnosis of painless longitudinal erythronychia, an infrequent manifestation. Proper diagnosis is essential to differentiate these lesions from malignant chondrosarcomas, which have a different management approach.