Tucked away on a quiet cul-de-sac in the Annex - right next to Yorkville - this 5+1 bedroom, 2-bath Victorian semi blends timeless character with modern flexibility in one of Toronto's most desirable neighbourhoods. Step through a rounded arch entrance and into a New York-style foyer with double transom windows. The spacious living room features soaring ceilings, original hardwood floors, a classic fireplace flanked by alcoves, and two tall front windows that flood the space with natural light. A large adjoining dining room (currently used as a family room) showcases high baseboard moulding and a generous window, enhancing the home's historic charm. The renovated eat-in kitchen offers butcher block counters, a rich brick backsplash, and ample storage. Walk out to a beautifully landscaped, ultra-private backyard with slate stonework and towering greenery - an ideal retreat for entertaining. Upstairs, the second level hosts a king-sized primary bedroom with two large windows and a built-in closet. Two additional bedrooms (one currently a gym, one ideal as a nursery or office) share a sleek modern bath with a glass walk-in shower. A deep hallway closet adds extra convenience. The third floor features two more bedrooms under gabled ceilings, one with a charming alcove perfect for a reading nook. The lower level includes a bedroom, workshop space with custom counters, a mini-fridge, laundry, bathroom, and ample storage which could be easily converted to a rec room, studio, or guest suite. All just steps from Yorkville's upscale shops, fine dining, cafes, U of T, Jesse Ketchum Jr and Sr PS, and Bloor Streets cultural corridor, this is sophisticated urban living in the heart of the city.