Leaside Homes for Sale

Leaside Homes for Sale

Welcome to Leaside, one of Toronto's most cherished neighborhoods, where charm meets convenience! Nestled in the heart of East York, Leaside is renowned for its picturesque streets, vibrant community spirit, and an array of amenities that cater to families, professionals, and retirees alike.

Leaside boasts a rich history, characterized by its beautiful tree-lined streets and an architectural mix of classic homes and modern builds. Whether you’re searching for a cozy bungalow or an elegant two-storey family home, there’s something for everyone in Leaside. The real estate market here is thriving, with a variety of homes for sale that reflect the neighborhood's unique character and appeal. Many properties feature spacious backyards, perfect for summer barbecues, and are located within walking distance to local parks and schools.

Beyond the beautiful homes, Leaside offers an abundance of local shops, cafes, and restaurants that create a vibrant community atmosphere. Enjoy a leisurely stroll through the Leaside Village Shopping Centre, or indulge in a delightful meal at one of the many local eateries. For families, the area is served by excellent schools, making it a sought-after location for those looking to plant roots.

With easy access to public transportation and major highways, commuting to downtown Toronto is a breeze. Whether you’re a first-time homebuyer or looking to upgrade, Leaside is a neighborhood that truly has it all. Explore the homes for sale in this charming community today and discover why so many are proud to call Leaside home!

Newest Leaside Homes for Sale

35 Bessborough Drive, Toronto
$3,650,000
5 Beds ⋅ 5 Baths ⋅ C14011372 MLS
A rare offering on Bessborough in the heart of Leaside: a beautifully renovated 3-bedroom 3-bathroom home home paired with a brand-new, exceptionally finished 2+1 bedroom 2 bathroom garden residence, creating a remarkable 5+1 bedroom living opportunity at almost 3000 square feet across two distinct homes.The main house has been extensively renovated with a warm, elevated finish throughout. The main floor features hardwood flooring, a wood-burning fireplace, a Cameo kitchen with Statuario marble backsplash and Caesarstone quartz countertops, built-in wine fridge, and a convenient office area just off the kitchen. Upstairs, three bedrooms include a vaulted-ceiling primary retreat with heated ensuite floors, while the finished lower level adds valuable living space with a steam shower, heated floors, gym area. New windows, central air, a cedar deck, updated driveway and landscaped outdoor space complete the home.Far beyond a traditional garden suite, the newly built rear residence has been designed and finished to the standard of a luxury home in its own right. Offering two bedrooms plus a flexible office, nursery or sitting area, it features a custom Irpinia kitchen and millwork, Miele appliances, marble backsplash, Caesarstone quartz countertops and seating for six at the island/peninsula. Radiant in-floor heating runs throughout both levels, while the primary suite includes a walk-in closet, grasscloth feature wall and spa-inspired ensuite with soaker tub and separate water closet. Second-floor laundry, air conditioning and a private interlock walkway complete the space.Ideal for multigenerational living,extended family, guests, passive income or those looking for exceptional flexibility, this is a unique opportunity to enjoy two beautifully finished residences on one of Leaside's most sought-after streets.

35 Bessborough Drive, Toronto
15 Moorehill Drive, Toronto
$3,900,000
6 Beds ⋅ 4 Baths ⋅ C14010858 MLS
An exceptional family residence set on a impressive 76-foot lot in prestigious Bennington Heights, this beautifully appointed home offers 4,772 sq ft of finished living space across three levels, including the built-in double garage. With five plus one bedrooms, four bathrooms, generous principal rooms, and outstanding privacy, it is thoughtfully designed for comfortable family living and effortless entertaining. The main level features gracious living and dining rooms, a custom kitchen, and an inviting family room at the heart of the home. French doors and multiple walkouts extend the interiors to the private backyard and charming side gardens, creating a seamless connection between indoor and outdoor living, while abundant natural light enhances the home throughout. Upstairs the private primary suite features two custom walk-in closets and a marble appointed ensuite. Four additional bedrooms are bright and generously proportioned, providing excellent space for children, family, and guests. The finished lower level offers exceptional versatility with a spacious recreation room and nanny's room, laundry facilities, cedar closet a workshop, and extensive storage, easily accommodating recreation and the practical needs of a growing household. Bennington Heights is cherished for its tranquil, family-oriented streets and strong sense of community. The home is moments from ravine trails, Bennington Park, and the shops, restaurants, cafe, and the amenities of Bayview Avenue. Nearby schools include Bennington Heights Elementary School, Bessborough Drive Elementary and Middle School, and Leaside High School. A distinguished Bennington Heights residence offering exceptional space, privacy and family living.

15 Moorehill Drive, Toronto
16B Kenrae Road, Toronto
$1,980,000
3 Beds ⋅ 4 Baths ⋅ C13861416 MLS
Welcome to 16B Kenrae Road, an exceptional custom-built three-bedroom, four-bathroom semi-detached home in the sought-after South Leaside neighbourhood. Thoughtfully designed with an emphasis on quality, style, and functionality, this impressive residence showcases high-end finishes, soaring ceilings, expansive windows, built-in speakers throughout, and beautifully proportioned open-concept living spaces throughout. The main level is centred around a spectacular chef-style kitchen featuring a built-in island, premium Wolf and Sub-Zero appliances, abundant cabinetry, and exceptional storage. The bright and spacious principal rooms provide the perfect setting for both everyday living and entertaining, with a walkout leading to a beautiful rear deck and tranquil outdoor space. A stylish powder room completes the main floor.Upstairs, the spacious primary retreat offers a serene escape with a luxurious four-piece ensuite, while the generously sized second and third bedrooms share a well-appointed bathroom. The lower level further enhances the home's versatility, offering direct interior access to the one-car garage, a full bathroom, roughed-in kitchen, and a bright walkout to the beautifully landscaped backyard with built in irrigation, creating an ideal space for a recreation room, guest suite, or additional living area.Outside, the property is equally impressive, featuring exceptional landscaping and mature greenery, a private heated driveway and front stairway, elegant porcelain facade, and a beautifully designed backyard oasis. Located in one of Toronto's most desirable family-friendly neighbourhoods, this exceptional home combines sophisticated design with thoughtful functionality in a prime South Leaside setting. A rare opportunity not to be missed.

16B Kenrae Road, Toronto
817 Millwood Road, Toronto
$2,048,000
3 Beds ⋅ 3 Baths ⋅ C13857122 MLS
Beautifully Renovated South Leaside Family Home! Lovingly cared for and thoughtfully renovated, this detached home offers a warm, functional layout in one of Toronto's most sought-after family neighbourhoods. The bright main floor features an elegant living room featuring a wood-burning fireplace and a completely renovated kitchen and dining area, creating an inviting space for everyday living and entertaining. Upstairs, you'll find three comfortable bedrooms and beautifully updated bathrooms. The perfect layout for everyday life. The fully finished lower level adds valuable living space with a spacious recreation room, an additional 3-piece bathroom, laundry, and plenty of storage-perfect for a kids' playroom, family room, or home office. A finished attic provides even more flexible bonus space. Outside, enjoy an incredible private backyard with plenty of room for kids to play, entertain, and relax, plus a large shed for additional storage. Freshly painted, meticulously maintained, and truly move-in ready. Complete with parking and ideally located just steps from excellent schools, parks, shops, restaurants, and TTC. A wonderful opportunity to put down roots in the heart of South Leaside.

817 Millwood Road, Toronto
63 Thursfield Crescent, Toronto
$1,190,000
4 Beds ⋅ 2 Baths ⋅ C13857082 MLS
Welcome to 63 Thursfield Crescent, a charming family home tucked away on a quiet, tree-lined street in the heart of highly sought-after North Leaside. Offering a wonderful blend of warmth, functionality, and flexibility, this inviting residence provides comfortable living spaces designed to grow with you. The main floor offers an easy flow for everyday living and entertaining, while the home's multiple bedrooms and finished lower level provide plenty of room for family, guests, a home office, or recreation space. Outdoors, enjoy a private backyard with a rear deck and space to relax, entertain, and play. A rear garage adds valuable versatility for parking, storage, or additional workspace. Ideally located within the coveted Northlea Public and Leaside Secondary School districts and surrounded by parks, shops, restaurants, transit, and the everyday conveniences that make Leaside such a beloved neighbourhood. A fantastic opportunity to settle into an established community and make this home your own.

63 Thursfield Crescent, Toronto
4 Douglas Crescent, Toronto
$4,999,000
5 Beds ⋅ 5 Baths ⋅ C13854620 MLS
You don't want to miss this one! Welcome to 4 Douglas Crescent, a truly exceptional architectural home on the edge of North Rosedale, offering 4+1 bedrooms, 5 bathrooms, and a remarkable blend of luxury, innovation, and functionality. Featuring hickory wide-plank flooring, heated marble floors, 9 skylights, custom lighting, Control4 automation, smart glass windows, extensive security, and 50+ surround-sound speakers, every detail has been thoughtfully designed. The backyard is pre-wired and pre-plumbed for a BBQ, hot tub, fire and water features, while the impressive garage offers a 6,000-lb. car lift, heated floors, EV charger, car-wash setup, and heated driveway with parking for four. A rare turnkey opportunity in one of Toronto's most exclusive neighborhoods.

4 Douglas Crescent, Toronto
153 Parkhurst Boulevard, Toronto
$1,375,000
4 Beds ⋅ 2 Baths ⋅ C13847594 MLS
Welcome to 153 Parkhurst Boulevard, a wonderful opportunity to own an updated family home in the heart of highly sought after Leaside. This charming three-bedroom, semi-detached home is situated on a large lot and offers the perfect blend of comfort, flexibility and future potential. Featuring bright and inviting principal rooms, hardwood floors, an updated kitchen with granite countertops overlooking the private backyard and a walkout from the dining room to a spacious deck, this home is ideal for everyday family living and entertaining. The finished lower level, with a separate entrance, adds exceptional versatility, offering a living area with kitchenette, a bedroom, and an ensuite bathroom. Whether you're looking for an in-law suite, nanny quarters or potential short-term rental opportunities, this space provides many possibilities. Outside, enjoy a private deck and fenced backyard, perfect for summer gatherings, children at play, or simply relaxing outdoors. A single garage and separate driveway provide convenient parking and additional storage. Move in and enjoy as-is, renovate to suit your tastes, or explore the potential to expand and create your dream home in one of Toronto's most family-friendly and desirable neighbourhoods. Just steps to top-rated schools, parks, transit, shopping, and all the amenities that make Leaside one of the city's most coveted communities.

153 Parkhurst Boulevard, Toronto
4 Kenrae Road, Toronto
$999,000
2 Beds ⋅ 2 Baths ⋅ C13847516 MLS
Welcome to this charming semi-detached home in the heart of Leaside, offering a wonderful combination of comfort, flexibility and location. Featuring 2 bedrooms with the option to easily convert back to 3 bedrooms, along with 2 bathrooms, this home offers over 1600 square feet of total living space and is perfectly suited to families, professionals or those looking for additional space to grow. The updated kitchen featuring a chef's gas stove, heated floor and skylight offers a bright, fresh, functional setting for everyday living and entertaining, while the home has been newly painted throughout, creating a bright and inviting atmosphere. Step outside and discover a deep, paved, low-maintenance backyard - an exceptional outdoor extension of the living space featuring mature trees for additional privacy. A tranquil pond feature adds charm and character, creating a peaceful setting for morning coffee, entertaining or simply enjoying the outdoors. Ideally situated in one of Toronto's most desirable family neighbourhoods, this home boasts a strong 92 walk score aka "Walker's Paradise", your daily errands do not require a car! Likewise, the home is conveniently located near the new TTC Line 5 Eglinton LRT (Laird Station), as well as the TTC #88 bus to St. Clair Station (Line 1) providing excellent access across the city. Families will appreciate being within the catchment areas for Rolph Road Public School, Bessborough Middle School and Leaside High School, as well as St. Anselm (Catholic JK-Gr8), all highly regarded local schools. Immediately enjoy everything Leaside has to offer, including parks, recreation, shopping, restaurants, community amenities and convenient transportation - all while being tucked into a welcoming residential Leaside neighbourhood.

4 Kenrae Road, Toronto
122 Brentcliffe Road, Toronto
$2,299,000
5 Beds ⋅ 4 Baths ⋅ C13844564 MLS
Welcome to 122 Brentcliffe Road, a bright and inviting family home in the highly sought-after community of Leaside. Warm, welcoming and thoughtfully laid out, this home offers beautiful hardwood floors, generous principal rooms and a functional floor plan designed to grow with you. The sun-filled living room is anchored by a charming wood-burning fireplace, while the kitchen walks out to a spacious deck and lush, exceptionally private backyard, creating an effortless setting for everyday family life and entertaining. Upstairs, three comfortable bedrooms are joined by an open den/office with the potential flexibility to become a fourth bedroom as your family grows. The spacious primary retreat features double-door entry, a beautifully updated ensuite and a generous closet with excellent potential to customize into a walk-in. The lower level adds another layer of versatility, with a separate entrance, kitchen, bedroom, bathroom, living room with a second wood-burning fireplace, separate laundry and brand-new flooring, ideal for extended family, guests or potential rental income. All of this in an exceptional northeast Leaside location, moments from Sunnybrook Park and the Don Valley's extensive trails and green space, and close to transit, shopping, everyday amenities and highly regarded local schools including Leaside High School. A wonderfully comfortable home today, with the flexibility to evolve for years to come.

122 Brentcliffe Road, Toronto
45 Mcrae Drive, Toronto
$1,995,000
4 Beds ⋅ 2 Baths ⋅ C13842740 MLS
Welcome To This Exceptional Detached 2-Story Home On A Premium 30.58 x 120 Ft South-Facing Lot, private Drive, In Highly Coveted South Leaside! Steps To Top-Tier Schools Including Rolph Road Elementary, Bessborough Drive & Leaside High School. Enjoy Seamless Transit, Easy Commuting & The Beautiful, Vibrant Vibe of Bayview Avenue's Renowned Shops & Restaurants. Professionally Landscaped Grounds Feature Multi-Zone Irrigation & A Resort-Style Backyard W/ Inground Pool, Waterfall Accent & Custom Poolside Cabana. Double Side-Yard Sheds + Private 2-Car Drive.Sophisticated Open-Concept Main Level Features Hardwood Floors, Crown Moulding, LED Lighting & California Shutters. Cozy Wood-Burning Fireplace In Living Room Flows Into Seamless Dining Space. Chef's Kitchen Boasts Updated Cabinetry, Quartz Surfaces, 3-Seat Peninsula & Dedicated Built-In Beverage Centre.Upper Level Offers 3 Bright Bedrooms W/ Hardwood & Primary Retreat W/ Double Closet. Fully Renovated 5-Pc Spa-Like Washroom Features Dual Vanities, Frameless Glass Shower & Luxury Heated Floors. Fully Finished Lower Level Adds Massive Footprint W/ Sprawling Rec Room, Quiet Dedicated Home Office, Functional Laundry, 3-Pc Bath & Tons of Storage!We Appreciate Your Interest In This Spectacular Property and Warmly Welcome You to Experience the Perfect Blend of Luxury, Comfort, and Neighborhood Charm. Come Tour This Exceptional South Leaside Masterpiece and Discover Your Next Dream Home! Don't miss the virtual tour.

45 Mcrae Drive, Toronto
319 Rumsey Road, Toronto
$3,589,000
4 Beds ⋅ 4 Baths ⋅ C13831502 MLS
Welcome to 319 Rumsey Rd, a beautifully renovated 2,600 sq. ft. home in the highly sought-after Leaside community! This exceptional residence features 4 spacious bedrooms and 4 bathrooms, offering plenty of room for comfortable family living. 2 bathrooms on the 2nd floor have floor heating. One heater in the garage too. 2 skylights are making a lot of natural sunlight. Situated on a well-landscaped 35 x 135 ft lot, the property boasts a private driveway with parking for 2 cars and a built-in garage. Enjoy a functional layout, stylish renovations, and a fantastic family-friendly neighbourhood surrounded by excellent schools, parks, shopping, restaurants, and transit. Conveniently located near Bayview Avenue, Laird Drive, Eglinton Avenue, TTC, and the Eglinton Crosstown. A wonderful opportunity to move in and enjoy everything Leaside has to offer!

319 Rumsey Road, Toronto
38 Killdeer Crescent, Toronto
$3,895,000
4 Beds ⋅ 3 Baths ⋅ C13830842 MLS
Tucked away on one of North Leaside's most coveted streets, this exceptional ravine property offers a rare sense of space, privacy, and possibility. While its street frontage is understated, the pie-shaped lot widens almost immediately from the street, unfolding into an extraordinary park-like setting surrounded by mature greenery and overlooking the ravine.The existing detached bungalow offers over 2,000 square feet above grade, with generous principal rooms, three bedrooms, and expansive views across the property. A family room, with incredible vaulted ceiling, and primary bedroom overlooking the ravine make the natural setting an integral part of everyday life. The recently renovated lower level, fully above grade at the rear of the home with multiple walk-outs, adds remarkable flexibility with additional living, working, and guest space. For those drawn to the ease and scale of bungalow living, the home presents an increasingly rare opportunity to enjoy a substantial footprint in one of Toronto's most established neighbourhoods. For others, the nearly 300-foot-deep lot offers an extraordinary canvas upon which to create a one-of-a-kind custom residence in a truly special setting. Moments from Serena Gundy and Sunnybrook Parks, excellent schools, and the amenities of Leaside, this is a unique opportunity where exceptional land, ravine privacy, and long-term potential come together.

38 Killdeer Crescent, Toronto
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