Listed by Royal Lepage Terrequity Seymour Real Estate.

344 Bessborough Drive is a Detached, 2-Storey and is currently for Sale @ $4,199,000. Taxes in 2025 were $17,759.00.

More homes for sale under 4.2M in Toronto

The moment you step into 344 Bessborough, you understand why North Leaside commands respect. The 2-Storey on 344 Bessborough Drive has 4 bedrooms, 5 bathrooms, and is located on a 135 x 40.05 ft lot in the community of Leaside . 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.

All existing appliances: Wolf 6-burner gas range, Sub-Zero paneled refrigerator, Sub-Zero beverage fridge (butler's pantry), Miele dishwasher, Wolf microwave, built-in range hood, side-by-side Miele washer & dryer (2nd floor laundry), Electrolux washer & dryer (lower level laundry), stainless steel refrigerator (lower level kitchen), stainless steel stove (lower level kitchen), stainless steel dishwasher (lower level kitchen) All electrical light fixtures. Hunter Douglas window blinds throughout. Sump pump. Rods and curtains in the primary bedroom & 3rd bedroom. All custom built-in shelving & closets throughout the home. Network box in kitchen. Reverse osmosis water filtration system. Central vacuum. Air exchanger. Humidifier. Master steam shower rough-in

The address 344 Bessborough Drive was listed for sale (MLS# C12872310) on Wednesday, March 11, 2026.