At the Windsor Arms, historic and new-millennium amenities are fused together to create a delicate balance of old-world charm and modern decadence. In fact, the building dates back to 1927 when the University of Toronto, with its neo-Gothic buildings and distinctive piers, porches, and crests were architectural marvels of the burgeoning metropolis. And that's exactly how hotelier, William Arthur Price, envisioned the four-storey building way back in the 30s. The original idea was to create a hotel residence to blend in with the university's signature, Victorian buildings. When completed, guests and passersby wondered whether Price had stamped the outside crest with his initials or that of the hotel. The question still remains to this day.

Years later, in 1966, the hotel entered Toronto's culinary scene, opening its restaurant, Three Small Rooms. The Courtyard Cafe was launched in 1976 and that same year, Club 22 opened as part of the city's growing nightlife.

By the late 80's, years of neglect took hold and in 1991 the Windsor Arms was shutdown with no prospects of reopening, that is, until developer George Friedmann sparked a vision of resurrection.

After purchasing the property in 1995, Friedmann commissioned architect, Sol Wassermuhl of Page + Steele to maintain the original characteristics from the stained glass window facing St. Thomas Street to the stone portico and vestibule in the entrance, but otherwise to completely rebuild the hotel and add condominium homes atop. Consultants from around the world descended on the plans and the results were custom mahogany furnishings based on 1920s French styles, rooms with cozy fireplaces, and bathrooms with limestone floors and walls, all in a modern, contemporary setting.