The moment you step into 344 Bessborough, you understand why North Leaside commands respect. This is heritage Toronto - the kind of neighbourhood where mature maples line streets that have watched the city grow for a century. And this property? It's the Leaside difference in full. Built in 2013 by Ivey Glenn - a builder known for construction quality over cost-cutting - this home offers 4,741 square feet across three fully finished levels. That number matters. At $4.2M, comparable in Moore Park and Lawrence Park rarely exceed 3,500 square feet. Here, the space is genuine. Main floor ceilings rise to 10 feet. The living and dining rooms flow with proportion and light. The kitchen opens naturally into a generous family room with double walkouts to a 727- square-foot wood deck - not a patio, an outdoor room. Upstairs, the primary suite features a cathedral ceiling, Juliette balcony, and dedicated dressing area. Bedroom 2 has its own ensuite and walk-in closet. Bedroom 3 is oversized. Five bathrooms in total, upper-floor laundry, and space that never forces compromise. The lower level earns the home its versatility. Nearly 1,500 finished square feet with close to 9-foot ceilings, a full second kitchen, bedroom, recreation room, 4-piece bath, dedicated laundry, and a walk-out to the garden. It functions entirely independently - ideal for extended family, live-in help, or guests who prefer their own space. Three gas fireplaces. Two laundry rooms. Attached garage with private drive. TTC transit one minute on foot. Leaside High School in seven. Sherwood Park in five. Sunnybrook less than a kilometre away.