For Sale | $2,379,000

147 Bessborough Drive

Property Description

Welcome to this fabulous 2-storey detached home featuring 3 bedrooms and 2 bathrooms, located in the highly sought-after Leaside neighbourhood. Available for the first time in 45 years, this South Leaside property sits on one of the area’s most desirable streets, lined with canopy trees, boulevards, and large lots.

This well-maintained home retains its original charm and offers immediate move-in appeal thanks to its generous 33 x 135 ft lot size. For the most discerning buyer, it also presents tremendous future potential.

The main floor features hardwood flooring in the living room, dining room, and sunroom. The spacious living room boasts bay windows with a large display shelf, an electric fireplace, and a private glass door for added privacy. The kitchen is flooded with natural light from multiple windows, while the dining room flows seamlessly into the living room and sunroom, creating a warm, casual atmosphere throughout.

Step outside to the back deck and enjoy the beautifully landscaped, private garden—a perfect setting for relaxation.

Upstairs, you’ll find a 3-piece family bathroom with a large glass shower. All three bedrooms are complete with large windows, closets, and broadloom carpeting.

The lower level rounds out this charming home with a recreational/media room, laundry area, 3-piece bathroom, utility room, pantry closet, and ample additional storage space.

Additional highlights include a private driveway, detached garage, professional landscaping, and an irrigation system in both the front and backyard.

The main floor balances character and comfort with ease. From the moment you enter, you’re welcomed by classic details like leaded glass, wainscoting, and warm hardwood floors. The living room offers a cozy focal point with a custom electric fireplace and oversized bay windows, flowing seamlessly into the dining area and sunroom—perfect for both everyday living and entertaining. The sunroom, with its wraparound windows and garden views, is a serene escape drenched in natural light. Meanwhile, the bright galley kitchen is both charming and practical, complete with granite countertops, stainless steel appliances, and a built-in breakfast nook that overlooks the backyard.

Upstairs, comfort meets charm across three bright and well-sized bedrooms. The primary bedroom offers golden afternoon light and generous storage, while the second bedroom boasts garden views and calm morning sun. The third bedroom is perfect for a nursery, home office, or creative studio. A refreshed three-piece bathroom ties it all together with a glass shower and thoughtful touches that blend vintage character with modern convenience.

The lower level is full of potential—whether you need a cozy media room, a quiet workspace, or a playful rec area. Built-in shelving adds function, and recessed lighting keeps the space feeling bright. A spacious laundry area, 3-piece bathroom, and ample storage (including a large pantry closet) make this level as practical as it is comfortable. A separate side entry adds even more flexibility.

The magic continues outdoors with a professionally landscaped front and back yard, complete with an irrigation system for easy upkeep. The private backyard is a lush retreat, ideal for entertaining or unwinding in peace. A spacious deck connects seamlessly from the sunroom, offering indoor-outdoor living in one of Toronto’s most coveted neighbourhoods. A private drive and detached garage round out this exceptional South Leaside property.

The Neighbourhood

Inspired by the timeless charm of Rosedale, Leaside is one of Toronto’s most desirable midtown communities. Tucked between Bayview Avenue and Eglinton Avenue East, Leaside blends classic elegance with modern convenience, offering an exceptional quality of life for families, professionals, and discerning homeowners alike. Known for its stately Tudor-style homes, quiet tree-lined streets, and generous lot sizes, Leaside radiates both prestige and warmth. This highly sought-after neighbourhood is a favourite among upper-middle-class families seeking a refined yet family-friendly environment. Residents enjoy access to expansive green spaces such as Serena Gundy Park, Howard Talbot Park, and Trace Manes Park, along with premier recreational facilities like the Leaside Memorial Community Gardens with its arena and indoor pool. Beyond its residential appeal, Leaside offers a rich lifestyle experience. Bayview Avenue is the heart of the neighbourhood’s retail and dining scene, lined with independent boutiques, artisanal bakeries, gourmet grocers, and beloved restaurants. The area is also known for its specialty antique shops and local markets. Leaside’s mix of architectural styles—from charming bungalows to grand custom-built homes—provides a diverse real estate landscape, including a limited selection of upscale condos for those seeking low-maintenance luxury living.

Schools & Education

Leaside is home to some of the city’s top-performing schools, making it especially attractive for families with school-aged children. Notable institutions include:

  • Leaside High School – Renowned for its academic rigour and outstanding science programs
  • Bessborough Drive Elementary & Middle School – A highly regarded public school with strong community involvement
  • Northlea Elementary and Middle School – Known for its French Immersion and gifted programs
  • Rolph Road Elementary School – A small, nurturing school with strong academic foundations
  • St. Anselm Catholic School – A faith-based option with a reputation for excellence
  • Children’s Garden School and Leaside Children’s House Montessori – Offering alternative and early education with a focus on enrichment

Proximity to Toronto’s top private schools in neighbouring Rosedale and Deer Park—including The York School, Branksome Hall, and UCC—adds even more educational options for families.

Armin Yousefi


Realtor®, Senior Vice President, Sales, Top 1% in Dollar Volume (TRREB 2024)

ayousefi@sothebysrealty.ca

416.960.9995

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