Syphilis is a multi systemic infection caused by Treponema pallidum. Ocular manifestations of Syphilis have a myriad of presentations and severity. A 31year old male patient was referred from ophthalmology department as a case of chorioretinitis for screening for syphilis. Patient had diminished vision and redness of right eye for 2 months duration. History of premarital exposure and extramarital contact was present. Ocular examination revealed - Rt eye: conjunctival congestion and Argyll Robertson pupil; Lt eye: normal. Fundoscopy of right eye showed yellowish white retinal lesions, macular edema and hyperaemia and left eye was normal. No genital lesion, scars or cutaneous lesion was present. VDRL was reactive in 1 dilution, TPHA was positive; HIV test was negative; CSF revealed VDRL - Negative and TPHA - Negative. Patient was treated with Injection procaine penicillin 1.2 Million units intramuscularly daily for 21 days. The patient responded well to treatment and there was improvement in his vision. Ocular Syphilis can occur at any stage of Syphilis and may be the only presenting sign. Syphilis serology was positive confirming the disease. This case highlights the importance of syphilis with ocular manifestation - there by proving that diagnosis of syphilis based on ocular finding is clinically challenging.