Originally designed in 1908 by celebrated architect Eden Smith, this Rosedale landmark has been brilliantly reimagined and meticulously renovated to the highest standards. With over 8,900 sq.ft. of living space, the home blends classic architectural charm with sophisticated modern design, creating a rare opportunity in one of Toronto's most coveted neighbourhoods. Set on a deep ravine lot, the property has been reinforced to protect against erosion and offers stone stair access directly to the extensive ravine trail system a private escape into nature, all while being just steps to Yonge Street, the TTC, shops, and fine dining. Inside, the home is both grand and welcoming, featuring 6+1 bedrooms, 6 bathrooms, and a private office plus a second floor family room, perfectly suited for large scale family living and entertaining. The Chefs kitchen is a showpiece, designed with two oversized islands, heated floors, a breakfast area, dual ovens (including steam), and dual dishwashers one full-size and one drawer making it both highly functional and beautifully designed. A centrally located glass-doored elevator with custom metal paneling connects all levels, complementing the homes graceful flow. The lower level is exceptionally finished, with soaring 9'6" ceilings, radiant heated tile floors in the newer section, a dedicated gym area, naturally climate controlled wine storage, a walk-in cedar closet plus a second oversized closet, and even a full second kitchen for extended family, staff, or entertaining on a grand scale. Throughout, every element has been carefully considered bespoke millwork, curated materials, and architectural details that preserve the homes character while adding contemporary luxury. This is more than a residence: it is a true Rosedale dame offered for the first time in over 20 years, updated for modern living, ready to be enjoyed for generations to come.