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344 BESSBOROUGH DRIVE, TORONTO, ON M4G 3L2

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344 Bessborough Drive
Toronto, ON M4G 3L2

$4,199,000

Beds: 5
Baths: 5
Sq. Ft. Range: 3000-3500
Type: House
Listing #C12872310
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.
Property Features
Location Information
Community: Leaside
Area: Toronto
Cross Street: Bayview/ Glenvale
Toronto Municipality: Toronto C11
City Area: Toronto C11
Interior Features
Bedrooms Above Grade: 4
Bedrooms Below Grade: 1
Interior: 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
Primary Bedroom Description: Hardwood Floor, 5 Pc Ensuite, Walk-In Closet(s)
Full Baths: 5
Has Dining Room: Yes
Dining Room Description: Hardwood Floor, Coffered Ceiling(s), Built-in Speakers
Has Family Room: Yes
Family Room Description: Hardwood Floor, Gas Fireplace, B/I Desk
Living Room Description: Hardwood Floor, Gas Fireplace, B/I Shelves
Kitchen Description: Eat-in Kitchen, Modern Kitchen, Window, Hardwood Floor, Modern Kitchen, Breakfast Area
Has Fireplace: Yes
Fireplace Description: Family Room, Living Room, Rec Room
Heating: Forced Air
Heating Fuel: Gas
Cooling: Central Air
Basement Description: Apartment, Finished with Walk-Out, Full
Has Basement: Yes
Exterior Features
Style: 2-Storey
Construction: Brick, Stone
Exterior: Deck, Landscaped, Patio, Paved Yard, Privacy, Porch
Foundation: Poured Concrete
Roof: Asphalt Rolled, Asphalt Shingle
Septic or Sewer: Sewer
Security Features: Alarm System
Parking Description: Private
Has Garage: Yes
Garage Spaces: 1
Total Parking Spaces: 2
Pool Description: None
Exposure Faces: West
Garage Description: Built-In
Has Waterfront: No
Features: Fenced Yard, Hospital, Library, Park, Place Of Worship, Public Transit
Additional Information
Possession: TBD
Property Type: SFR
Property SubType: Detached
Age: 6-15
Parcel Number: 103650021
Status: Active
Tax Year: 2025
Tax Amount: $17,759
Transaction Type: For Sale


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Monthly Tax: $
Monthly Insurance: $
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Based on a fully amortized fixed rate loan. Ask your agent for the tax rates in your area. Insurance estimate is based on an average cost, your final premium cost will be determined by the type of coverage you select. This program only provides an estimate.
Listing Courtesy of ROYAL LEPAGE TERREQUITY SEYMOUR REAL ESTATE
© 2026 Toronto Regional Real Estate Board. All rights reserved.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate, of the type being offered via this website. Data is deemed reliable but is not guaranteed accurate by the Toronto Regional Real Estate Board (TRREB). In Canada, the trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
TRREB - Toronto data last updated at March 16, 2026, 10:05 PM ET
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