Prime semi where Summerhill meets the Annex at centre ice! Look no further than this incredible entry-level home offering exceptional flexibility in one of Toronto's most coveted neighbourhoods. Currently configured as 2 self-contained suites, this gorgeous red-brick house blends warmth, function and income potential with exposed brick walls, wood-burning fireplaces, generous ceiling heights, wide-plank oak flooring, updated kitchens and inviting principal rooms. The second floor is an open-concept, NY loft-like living space w/ a wall of exposed red brick, offering a bright, renovated kitchen with quartz counters, stainless steel appliances, subway tile backsplash and custom cabinetry. The space is completed with a spacious dining area and a generously sized living room with a bay window and fireplace. The third floor features a private primary retreat, den area, stylish 4-piece bath and walkout to a rooftop deck surrounded by mature trees. The main floor suite has its own charm, with exposed brick, a cozy fireplace, updated kitchen, 4-piece bath, bedroom with walkout to a rear deck and access to a partially finished basement with in-suite laundry, storage and recreation space. Enjoy 2-car rear laneway parking, multiple outdoor spaces, and the perfect covered front porch for summer nights in midtown Toronto. Steps to Yorkville, The Annex, Summerhill, Ramsden Park, Dupont Station, George Brown, shops, cafes and restaurants. 75 Dupont Street offers rare flexibility without compromise, surrounded by everyday conveniences, excellent walkability and seamless transit access in every direction.