Rare, move-in ready, and full of potential, this exceptional residence offers remarkable flexibility--perfect as a single-family home, intergenerational retreat, or rental duplex. Boasting 5 generously sized bedrooms and 2 full kitchens, it easily accommodates growing families, extended living arrangements, or income opportunities. Nestled on a coveted street in the highly desirable Roncesvalles/High Park neighbourhood, the home blends timeless character with modern confidence, supported by solid mechanical systems and a strong inspection report. This remarkable early-1900s brick home is one of the original 12 duplexes built in High Park, set on an expansive lot measuring 191' x 29' x 162' x 41'. Rich in character, it retains many original features while offering approximately 4,000 square feet of living space, including an unfinished basement ready for customization. The home has uniquely large principal rooms and bedrooms, creating a grand, mansion-like feel across its 13 rooms. Currently configured to function as either a single-family residence or two separate units, the property presents numerous possibilities for future enhancements, subject to municipal approvals, such as transforming the second-floor kitchen into a spa-inspired bathroom, adding a third-storey extension for additional living space, or creating extra parking, a garage, or even a garden suite in the backyard. Ideally located, the home is just an easy stroll to the shops and restaurants along Roncesvalles, as well as the vibrant Queen Street corridor, with convenient access to the UP Express station, streetcars, and subway. Enjoy glimpses of Lake Ontario from the house, all within a top-rated school catchment area, making this an exceptional opportunity for families and investors alike. This is a rare chance to secure a property with both immediate comfort, long-term potential and stunning curb appeal in one of Toronto's most sought-after communities.