Welcome to 93 Medland Crescent - a charming, character-filled legal duplex with a beautifully finished basement suite in the heart of High Park North. Thoughtfully updated and lovingly maintained, this multi-unit home offers incredible flexibility for live/rent buyers seeking lifestyle, location, and long-term value. Boasting nearly 2,000 square feet above grade plus a 685 sq ft lower level, this home features three distinct suites - ideal for multigenerational living or generating reliable income. The upper bi-level 2-bedroom skylit suite impresses with a cozy gas fireplace, private deck walk-out, and classic hardwood charm. A stylish 1-bedroom bi-level suite walks out to the serene backyard garden, while the lower-level apartment is bright and inviting with high ceilings and a smart layout thanks to a professionally underpinned basement. This home is turnkey! The bonus? Two parking spaces via rear lane, a rarity in this walkable west-end neighborhood. Steps to Keele Station, High Park, The Junction, and Bloor West Village, you're surrounded by top schools, indie cafés, grocers, trails, transit, and community spirit. Whether you're a savvy buyer looking to live in one unit and rent the rest, or seeking space for extended family with built-in privacy - this is the one!