Tucked along one of the Annex's most coveted streets, 144 Howland Avenue is a rare offering. Set on an exceptional 25.58 x 150 ft lot, this semi-detached home provides a sense of space and scale rarely found in the neighbourhood. Fully renovated in 2010, the home blends timeless character with thoughtful modern updates, showcasing crown moulding, wainscoting, bay windows, and wood-burning fireplaces throughout. The main floor features a bright living room with a wood-burning fireplace and bay window, a spacious dining area overlooking the deep backyard, and a chef's kitchen with large marble island, ample storage, and convenient powder room. The second level offers exceptional flexibility with 3 bedrooms, including an expansive, light-filled space currently used as a family room and bedroom combination, but can easily be converted to create a five-bedroom layout. Complete with a fireplace, custom built-ins, and upper-level laundry. The third floor is a dedicated primary retreat, featuring a separate office or nursery space, a spacious bedroom with sitting area, a custom walk-in closet, and a beautifully renovated six-piece ensuite (2025) with marble floors, freestanding tub, glass shower, and double vanities. The lower level includes a self-contained 1-bedroom suite with full-sized appliances and separate laundry, ideal for additional rental income or extended family visits. All of this in a prime Annex location, just steps to Bloor or Dupont, TTC, and some of the best cafés, restaurants, and shops that the city has to offer.