Rare 40' x 153' East-Facing Lot in Chaplin Estates! This impressive 5 bedrooms + Office residence perfectly balances 1920s architectural soul with an extensive, modern structural evolution. Behind the classic façade lies a home engineered for the future: fully upgraded 200A electrical (no knob & tube), a new high-efficiency boiler/on-demand HW system, and a comprehensive water management system with battery backup and totally upgraded plumbing. The sprawling floor plan features a sun-filled main floor family room addition with a wood-burning fireplace and walk-out to a massive 990 sq. ft. stone terrace - an entertainer's dream. The 1926 heritage shines through original beveled French doors, wainscoting, and crown molding, while the newly completed 3rd-floor sanctuary offers high ceilings, Pella windows, and a designer 4-pc bath with skylight. Key Highlights: Primary Suite: East-facing garden views, large dressing area, and 5-pc ensuite. Modern Comfort: Dual-zone climate control (Rads + Forced Air AC/Heat) and a gutted main-floor powder room with in-floor heating. Lower Level: High-ceilinged "Great Room" addition with fireplace - Ideal for a gym, cinema, or privately located office. Parking: Highly coveted Private Driveway leading to a Newly Built Garage (2024). A short walk to the Beltline Trail, Eglinton LRT/Subway, world-class shopping / dining and the city's top-tier schools (Oriole Park JPS, UCC, BSS, Havergal, North Toronto). A solid, mechanically superior foundation in one of Toronto's most prestigious pockets. Move in and enjoy or further customize to create your forever home!