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Welcome to this remarkable 2-Storey detached located in the coveted neighborhood of Leaside. Expertly crafted featuring premium brick and stone construction, this residence presents an exceptional opportunity offered at $4,199,000 to acquire a beautiful home in a highly sought-after setting. Designed for both comfortable daily living and elegant entertaining, the layout maximizes natural light, functional flow, and lifestyle utility.
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.
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Fenced Yard, Hospital, Library, Park, Place Of Worship, Public Transit
Air Exchanger, Auto Garage Door Remote, Bar Fridge, Central Vacuum, ERV/HRV, Floor Drain, In-Law Capability, In-Law Suite, Storage, Sump Pump, Water Heater Owned
Alarm System
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This could be the first listing for this address.
Data-driven valuation for 344 Bessborough Drive, Toronto C11, ON M4G 3L2
Based on 0 recent similar sales in the pocket.
Properties in this area are selling at a steady pace.
Calculate your monthly payment, minimum downpayment, and land transfer taxes for this home in Toronto.
About Purchasing a Home in Toronto, ON
For a property listed at $4,199,000 in Toronto, the legal minimum down payment is $839,800 under current Canadian banking regulations. This calculation applies a 5% requirement on the first $500,000, 10% on the next $499,999, and a flat 20% on any amount exceeding $1,000,000.
Additionally, buyers in Ontario must budget for the Provincial Land Transfer Tax, which is estimated at $91,450 for this transaction. Since the property is located in Toronto, a municipal land transfer tax of $91,450 also applies, bringing the total estimated land transfer taxes to $182,900.
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Disclaimer: AI Insights are generated by an automated system and should be used for informational purposes only. While we strive for accuracy using current market data and deep-learning models, these assessments do not constitute professional real estate, legal, or financial advice. All property values, predictions, and scores are estimates. We strongly recommend verifying all property details and conducting independent due diligence with a licensed professional before making any purchase decisions.