This paper looks at architectural reconstruction of Virupaksha Bazaar Street, of Hampi, a UNESCO World Heritage site of Vijayanagara period (1327-1674 AD), located in South India. The paper discusses the methods and rules applied to arrive at conjectural reconstruction of the structures. The Virupaksha street is 800 m long and 13.8 m wide with more than 50 structures placed close to one another with gap as less as 0.5 m. The architectural/site context changed constantly due to occupation, alteration and later evacuation. It has obstructions within and outside the structures, on the street and vegetation overgrowth. The digital reconstruction includes 2D drawings and 3D models for each structure, panoramic views from different station points of the street and walkthrough of the street in form of narrative video.