The Winchester Hotel building was constructed in 1888 as an addition to the existing hotel at 531-535 Parliament Street. In 1941, significant interior and exterior alterations were undertaken by architect Benjamin Swartz to reflect the contemporary Art Moderne style. In 1955, the lower portion of the property was clad in Granox by DeSpirit Mosaic and Marble Company Limited. The building was designated under Part IV of the Ontario Heritage Act in 1995.

In 2006, Stanford Downey Architects did restoration work focussed on the recovery of the original brick wall at grade. In 2009, a fire blazed through the top floor, but swift action by city firefighters prevented total destruction of the building. A large restoration project of the hotel using period methods and matching reconstructions to historical documentation of the building was completed by Hunt Heritage between 2019 and 2021.

Hunt Heritage's restoration of the Winchester Hotel included removing, re-laying, and repointing over 6,000 individual bricks using the time-consuming and meticulous traditional English tuckpointing method. Hunt's crew identified, restored, and preserved long-obscured original features such as a tiled floor mosaic bearing the hotel’s previous name, the “Lakeview” Hotel. They also famously reconstructed the hotel’s lost cupola lantern using blueprints drawn solely from archival photographs. Building the lantern required substantially reinforcing the existing cupola so that it could support an additional 7,000 pounds of historically accurate material. 

• Architect - Edward Cecil Strong Cox  <-- More buildings by this architect.
• Architect - Thomas Kennedy  <-- More buildings by this architect.
• Architect - Benjamin Swartz  <-- More buildings by this architect.
• Architect - Stanford Downey Architects Inc.  <-- More buildings by this architect.
• Decoration - DeSpirt Mosaic & Marble Co., Ltd.
• Developer - John Bernardo
• Restoration - Hunt Heritage