For locals, Indian Road is synonymous with dreamy, turn-of-the-century homes that sit like grand estates along a family-friendly, tree-lined street-just moments from the gates of the city’s greatest playground, High Park, and the vibrant Roncesvalles Village. Homes in this coveted pocket rarely become available, with everything needed to create a lifetime of memories right at your doorstep. Discover a rare investment opportunity with this beautifully configured legal triplex, offering three thoughtfully designed units within a charming three- storey home, complete with a separate walk-up basement. Blending timeless character with practical layouts, this property is ideal for investors, multi-generational living, or those seeking strong rental income potential. The upper two-storey unit spans the second and third levels, offering a spacious and inviting layout. The second floor features a bright family room anchored by a stunning vintage wood-burning fireplace with a gas insert, creating a warm and elegant focal point. A dedicated dining room, well-appointed kitchen, and convenient powder room complete this level. The third floor offers two generously sized bedrooms and a full bathroom, while an additional bedroom on the second floor provides flexibility for families or a home office. The main floor unit offers comfortable single-level living with two bedrooms, a functional kitchen, ample storage, and a full three-piece bathroom-an attractive and practical option for tenants or extended family. The finished walk-up basement unit offers excellent independence, featuring a kitchen, dining area, bedroom, full bathroom, and abundant storage. Offered for the first time in over 40 years, this property showcases timeless Edwardian architectural charm and presents a rare opportunity to unlock exceptional value in one of the city’s most desirable neighbourhoods.