Historic Elegance Meets Modern Luxury at 9 Wellington St. Experience the perfect blend of century-old charm and high-end functionality in this grand 1926 home located on one of Orangeville's most prestigious streets. Spanning an impressive 4201 sq ft, this residence features 2 kitchens with a self-contained apartment, and a total of 6 spacious bedrooms and 5 bathrooms, providing ample space for both grand living and cozy retreats. The main home welcomes you with a charming sunroom of wood and exposed brick, leading into a formal dining room & library space centered around one of the home's three gas fireplaces. Culinary enthusiasts will appreciate the open-concept kitchen's central island and rich wood cabinetry, which flows effortlessly into a great room anchored by a striking brick fireplace that walks out to your spacious back deck. Retreat to the primary suite to find 2 double closets and a spa-like 5-piece ensuite bathed in light from a large skylight. A 2nd stairwell to this level brings you to 3 more bedrooms and a shared 3 piece bathroom while yet another bedroom or additional living space can be found in the unique top-level loft. The 3 Level Apartment on the South side of the home features its own entrance through a stunning vestibule, a main floor eat-in kitchen that walks out to the back deck, lower level family room with walk-out to the yard, a 3rd story primary suite with gorgeous 3 piece ensuite & laundry hookups, and the convenience of its own furnace, and hot water tank. The perfect space for rental income or extended family. Set on a deep 63 x 188 ft lot, the private backyard serves as a secluded oasis with mature hedges, low-maintenance gardens, and a spacious, multi-level deck for entertaining. Located just moments from the award-winning restaurants & shops of Broadway, the Island Lake Conservation Area, and within walking distance to local schools, this home offers a peaceful lifestyle with every urban convenience at your doorstep.