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Eccrine syringofibroadenoma (ESFA) is a rare benign adnexal neoplasm characterized by eccrine ductal differentiation within a fibrovascular stroma and poses significant diagnostic challenges due to its variable clinical presentation. It may occur as a solitary lesion, a reactive proliferation in chronically inflamed or traumatized skin, or in association with hereditary syndromes. We report a case of a 47-year-old male presenting with a two-year history of asymptomatic, slowly enlarging nodules forming an annular plaque over the posterolateral aspect of the right foot. Dermoscopy revealed light-brown pigment globules in a cobblestone pattern with yellowish scales and central crusting. Histopathology demonstrated anastomosing epithelial cords with eccrine ductal differentiation embedded in a mucin-rich fibrovascular stroma, confirming ESFA. The lesion was treated with complete surgical excision, resulting in an excellent outcome. This case highlights the importance of clinicopathological correlation, the supportive role of dermoscopy, and the need for awareness of ESFA in chronic acral lesions.