18 Gloucester Lane presents a rare opportunity to acquire a five-storey commercial building discreetly tucked behind Yonge Street. Constructed in 1912 and thoughtfully modernized, the property spans approximately 9,792 square feet and showcases enduring architectural character, including buff brick construction, arched windows, exposed brick and beam, and expansive floor plates with industrial proportions. For more than four decades, this building served as the creative headquarters of internationally acclaimed Canadian filmmaker Norman Jewison. Within its walls, major productions were developed, produced, and edited, cementing its reputation as a cultural landmark within Toronto’s urban core. The property is currently configured as a boutique investment with four lower floors of offices leased to professional tenants. The top level is a dedicated private penthouse residence, offering a rare live/work dimension within the city. The penthouse features exposed walls and beams, custom millwork, and a dramatic herringbone brick fireplace anchoring the central living space. Large windows overlook Norman Jewison Park, and a concealed staircase leads to an upper suite. Positioned within the Historic Yonge Street Heritage Conservation District, 18 Gloucester Lane benefits from both centrality and discretion, with immediate access to the city’s transit, retail, cultural, and business corridors. Its laneway address enhances privacy while keeping it closely connected to Yonge Street and Bloor Street amenities. This property provides flexibility for investors, end-users, and institutions alike. It can continue as a boutique investment property, adapt to a private family office or foundation headquarters, transform into a design studio or gallery, or evolve into a fully integrated live/work residence. 18 Gloucester Lane is a unique convergence of architectural integrity, cultural provenance, and investment potential, offering the rare chance to steward one of Toronto’s most evocative laneway properties.