Tucked on a quiet street in the shadow of Upper Canada College and steps to BSS, this exceptional duplex offers unmatched scale, character, and location. With over 6,000 sq ft above grade, each residence spans approx. 2,880 sq ft, plus a third-floor office/bedroom with terrace in the upper suite. Both units feature grand 25 x 15 living rooms with wood-burning fireplaces, formal dining rooms with tall wainscoting and crown moulding, sun-filled dens, and spacious kitchens with pantry or eat-in areas. The ground-floor unit offers four bedrooms, including a 17 x 14 primary with semi-ensuite, a large secondary bedroom, and two additional bedrooms - one with built-in laundry - sharing a stylish 3-piece bath. The second-floor unit mirrors the layout, with one of the bedrooms transformed into a library, a dedicated 4-piece ensuite in the primary, and an airy, skylit kitchen with cathedral ceilings. A private office nook sits above the main floor foyer, while the third-floor office offers a walk-out terrace and walk-in closet. Additional highlights include renovated bathrooms, abundant storage, an unfinished 2,800+ sq ft basement with high ceilings and separate entrance, a finished dark room, and three parking spaces (two under a carport) waiting for your personal touches. A short walk to Eglinton and St. Clair shops, Davisville subway, and Avenue Road's direct downtown access, this property is ideal for end users, investors, or multi-generational living. This is a rare offering in a coveted midtown Toronto location.