Leaside Real Estate

Leaside Real Estate

Welcome to Leaside, one of Toronto's most cherished neighborhoods, where charm meets modern convenience! Nestled in the heart of Ontario, Leaside is a vibrant community known for its picturesque streets, lush parks, and a strong sense of belonging. With its tree-lined avenues and beautifully maintained homes, this area offers a perfect blend of suburban tranquility and urban accessibility.

Leaside is a family-friendly neighborhood with an abundance of amenities that cater to all ages. The area boasts top-rated schools, making it a sought-after destination for families looking to provide their children with an exceptional education. Residents enjoy easy access to a variety of recreational facilities, including the expansive Leaside Memorial Community Gardens, which features sports fields, a swimming pool, and walking trails that invite outdoor enthusiasts to explore.

Shopping and dining in Leaside are equally delightful. The bustling Bayview Avenue is lined with boutique shops, cafes, and restaurants that offer a diverse culinary scene, ensuring there's something to satisfy every palate. Whether you’re in the mood for a cozy brunch or a gourmet dinner, Leaside has you covered.

Additionally, Leaside's strategic location allows for seamless commuting to downtown Toronto, with quick access to public transit and major highways. This makes it an ideal choice for professionals who want to enjoy the vibrancy of city life while retreating to a peaceful neighborhood at the end of the day.

In Leaside, you’ll find not just a home, but a community filled with warmth, charm, and a lifestyle that truly embraces the best of Toronto living. Come and discover why so many are proud to call Leaside home!

Newest Listings in Leaside

122 Brentcliffe Road, Toronto
$2,299,000
5 Beds ⋅ 4 Baths ⋅ C14133866 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
10 Red Oaks Crescent, Toronto
$3,250,000
4 Beds ⋅ 3 Baths ⋅ C14129218 MLS
Set on a quiet, tree-lined street in coveted Bennington Heights, this beautifully renovated bungalow offers a rare combination of architectural warmth, thoughtful design, and an exceptional natural setting. Occupying a generous 56-foot frontage corner lot with southern and eastern exposures, the property is surrounded by mature trees, including magnolia, ginkgo, and catalpa, creating a lush, private retreat filled with natural light. Offering approximately 2,500 sq. ft. of finished living space across two levels, the home is defined by an understated contemporary aesthetic, where hardwood floors, custom millwork, and natural materials create inviting interiors. Generous principal rooms lead to a beautifully appointed custom kitchen with integrated appliances, while a striking family room addition with built-in custom cabinetry forms a seamless connection to the garden through an oversized lift-and-slide door. The primary bedroom features an ensuite bath, while radiant heated floors in all three bathrooms, the primary bedroom, and family room addition provide exceptional comfort. The finished lower level offers a spacious recreation room anchored by a wood-burning fireplace, a versatile bonus room ideally suited as a guest bedroom, home office, or gym, and a laundry room combined with a mudroom featuring separate access to the driveway, along with abundant storage. Beyond the home, Bennington Heights is one of Toronto's most cherished residential enclaves, celebrated for its winding streets, estate-sized properties, magnificent tree canopy, and remarkable sense of tranquility. Bordered by Moore Park Ravine, the neighbourhood offers a peaceful, community-oriented lifestyle with scenic trails, excellent schools, and the shops and restaurants of Bayview Avenue moments away. Minutes to downtown. A beautifully considered home in an extraordinary setting, offering the ease of living in one of the city's most desirable neighbourhoods.

10 Red Oaks Crescent, Toronto
442 Heath Street E, Toronto
$9,495,000
5 Beds ⋅ 5 Baths ⋅ C14127394 MLS
Welcome to 442 Heath Street East, an architecturally distinctive contemporary residence offering more than 6,000 square feet across three levels in coveted Bennington Heights, with interiors by Ashley Botten. Set on an extraordinary lot, this sun-filled home pairs luxurious finishes, thoughtful built-ins, in-floor heating throughout and a heated driveway for year-round comfort. A sleek and stunning entryway features extensive storage and introduces the elegant living and dining room, complete with show-stopping floor-to-ceiling windows. The stunning modern kitchen features a large island and adjoining breakfast area. The expansive family room overlooks the landscaped backyard, while a main-floor office, powder room and attached garage add everyday convenience. Upstairs are four spacious bedrooms, a family library and laundry room, including a spectacular primary retreat with backyard views, a skylit walk-in closet and luxurious five-piece ensuite. The lower level offers a generous recreation room, fifth bedroom, full bathroom, fitness and Pilates studio, infrared sauna and ample storage. And then there is the backyard, which is reminiscent of the most exclusive resorts in the world. Discover a gorgeous swimming pool, expansive entertaining patio, outdoor cooking area, children's play treehouse, butterfly garden, outdoor table tennis and additional green space beyond the pool. Expansive windows bring exceptional natural light into the home and frame its lush surroundings. Enjoy proximity to Moore Park Ravine, the Beltline Trail, Evergreen Brick Works, parks and Bayview Avenue's shops, cafes and restaurants. Nearby schools include Bennington Heights Elementary, Bessborough Drive Elementary and Middle School and Leaside High School (subject to school board policies), with convenient TTC connections, access to downtown and the Don Valley Parkway. A rare blend of modern architecture, family comfort and resort-inspired outdoor living, this home is truly exceptional.

442 Heath Street E, Toronto
112 Southvale Drive, Toronto
$2,175,000
5 Beds ⋅ 3 Baths ⋅ C14124338 MLS
Space for the whole family to enjoy at this well-appointed South Leaside home set on a 51 ft frontage! Beautifully renovated and well-maintained, you will enjoy the incredible layout combined with private drive and a deep, secluded backyard. A rare main-floor primary suite includes heated floors, generous wardrobe storage and a three-piece ensuite with curb-less glass shower and skylight. Over 2,600 square feet of total living space (1936 sq ft above grade). Hardwood floors, traditional millwork and classic detailing carry through generous principal rooms, including a beautiful open-concept living room with gas fireplace and dining room with wainscotting. The kitchen offers soft-close drawers and stone countertops, opening to the bright breakfast area and family room. Surrounded by windows and skylights, this inviting space features heated floors, a second gas fireplace and a walkout to the garden. Upstairs are three bedrooms and a four-piece bath, offering flexibility for family life or a home office. The finished lower level with a separate side entrance has a great recreation room with built-ins, a three-piece bath, laundry and storage, plus the additional bedroom (or work from home space or gym). The fully fenced backyard is framed by mature trees and greenery, with an interlock patio, irrigation, landscape lighting and garden shed. Steps to all that Leaside has to offer, parks and excellent schools, with Bayview and Laird amenities, transit and highway access nearby. Easy commute to downtown, or north to cottage country!

112 Southvale Drive, Toronto
770 Eglinton Avenue E, Toronto
$1,199,000
4 Beds ⋅ 2 Baths ⋅ C14120588 MLS
Discover exceptional space and versatility in the heart of Leaside with this charming, generously proportioned semi-detached home, offering an inviting layout and plenty of room to grow. Thoughtfully laid out with generous principal rooms, this home features a bright and inviting living room with a wood-burning fireplace, a separate dining area ideal for entertaining, and an updated kitchen with a walkout to a private rear deck and garden. Upstairs, three well-proportioned bedrooms offer comfortable family living, complemented by a four-piece bathroom. The finished lower level adds exceptional versatility, complete with a fourth bedroom, second kitchen, three-piece bathroom, and laundry area, offering flexible space for extended family, guests, or additional living needs. A detached garage provides convenient parking and storage. Ideally situated in sought-after Leaside, within the Northlea school district and close to neighbourhood parks, shops, restaurants, and everyday amenities. A wonderful opportunity to enjoy generous living space, a functional layout, and the convenience of one of Toronto's most established family-friendly neighbourhoods.

770 Eglinton Avenue E, Toronto
4 Kenrae Road, Toronto
$949,000
2 Beds ⋅ 2 Baths ⋅ C14115994 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. A great condo alternative! 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
34 Glenbrae Avenue, Toronto
$3,199,000
5 Beds ⋅ 4 Baths ⋅ C14115812 MLS
A spectacular one-of-a-kind North Leaside home that makes you dream of long summer days spent poolside, dinner underway in the outdoor kitchen, the game playing on the outdoor TV with evenings dining under the gazebo. This exceptional 4+1 bdrm, 4 bathroom home delivers luxury inside & out, with soaring ceilings, beautifully wallpapered accent walls and impeccable attention to detail. The open-concept living and dining boast a front bay window, while a fabulous built-in bar leads to the chef-inspired kitchen featuring an oversized centre island, pull-out pantry storage, a generous breakfast area perfect for busy family mornings. The oversized family room is a showstopper, with coffered ceilings, wall-to-wall custom built-ins and a gas fireplace, all framed with windows overlooking the backyard oasis. Step outside to your private retreat, stunning inground salt-water Gunite (concrete) pool w/sheer descent wall & 3 waterfalls, & the outdoor kitchen & pergola are designed for unforgettable family gatherings. Upstairs, the spacious primary bdrm offers a true private sanctuary with an oversized walk-in dressing room and 5 PC spa-inspired ensuite. Every bdrm features high-end custom closet cabinetry & another 5 PC bathroom. The lower level is equally impressive, w/oversized above-grade windows flooding the space with natural light, a large recreation room with wall-to-wall built-ins, a beautifully finished laundry room, abundant storage including a dedicated pantry room, and another gorgeous 3-piece bathroom all lead to the 5th bdrm now used as an elaborate home office. Families will appreciate the approx 8-minute walk to Northlea Elementary & Middle School (FR Immersion) then walking to the Eglinton/Laird LRT for work. Leaside Village is just a 5-minute drive away, with Longo's, Shoppers Drug Mart, restaurants, shops and everyday conveniences. A remarkable family home where everyday living feels like a holiday. Refer to Features & Upgrades attached.

34 Glenbrae Avenue, Toronto
10 Field Avenue, Toronto
$4,499,000
5 Beds ⋅ 5 Baths ⋅ C14106058 MLS
Welcome to 10 Field Ave. Primely located in the heart of South Leaside this rare offering is steps to Bessborough P.S & St. Anselm's. Completely renovated this unique property is a perfect forever family home. Offering over 5000 sf of living space! The main floor family room is a perfect place to host large gatherings, being over 400 sf of open-concept living with a walk-out to a secluded garden, pool & hot tub. The kitchen was renovated in 2020 and is truly a Chef's kitchen featuring: Subzero 36" fridge & 36" freezer, Wolf 48" 6-burner gas stove with a double oven and BBQ + a Professional line Wolf 48" exhaust, Miele coffee machine, steam oven, wine fridge & additional beverage fridge. Wall-to-wall pantry and tons of storage. A classic center hall layout with a formal Dining & Living room. (could be main floor office). The Primary suite is very spacious with a gas fireplace, "his and hers" ensuites (new 2026) & 2 walk-in closets. The bedrooms are generously sized. 2nd floor laundry room. Kids can kick off their shoes in the mudroom & head downstairs to the rec. room. The 5th bedroom is ideal for a live-in Nanny or could be a great gym. This home has TONS of storage & great parking! A sunny turnkey home on a premium double lot that pies to 53 ft.!

10 Field Avenue, Toronto
817 Millwood Road, Toronto
$1,949,000
3 Beds ⋅ 3 Baths ⋅ C14099652 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
32 Evergreen Gardens, Toronto
$2,798,000
4 Beds ⋅ 4 Baths ⋅ C14094926 MLS
NEW PRICE! Exceptional value in exclusive Bennington Heights. Part of an intimate luxury collection of just five bespoke residences, Three are sold, only two remain. Modern luxury meets architectural elegance in this multi-level home featuring ~4,000 sq. ft. of finished living space (3,000 sq. ft. above grade), a rare 20-ft interior width, and a private elevator accessing all 5 levels.Highlights include a Miele /Wolf chef's kitchen with marble counters, soaring main-floor ceilings, custom white oak finishes, linear fireplace, spa baths, and a finished basement with radiant heated floors. Enjoy multi-functional living with a ground-floor guest/office suite, 2-car parking (built-in garage), and an 800 sq. ft. south-facing rooftop terrace with a built-in pergola. Complete with full Tarion warranty and prime access to Bayview amenities, Beltline trails, and downtown transit routes. Open House Saturday October 31 2 to 4 Pm

32 Evergreen Gardens, Toronto
1618 Bayview Avenue W Unit B, Toronto
$48,888
C14094610 MLS
Excellent opportunity to acquire Arista Aesthetics, an established beauty and skincare clinic located in the heart of Leaside on Bayview Avenue. Offering a range of popular services, including laser hair removal, customized facials, microneedling, and waxing, this business presents an exciting opportunity for beauty and wellness entrepreneurs. Benefit from an established clientele and association with a successful hair salon, creating excellent potential for cross-referrals and continued growth. The new owner may also have the opportunity to expand the service menu to include additional aesthetic treatments, such as Botox, dermal fillers, and other skin rejuvenation services, subject to applicable licensing and regulatory requirements. Ideal for an owner-operator or beauty professional looking to grow their business in a desirable Toronto neighbourhood. Located just steps away from the vibrant shops, cafes, boutiques, and amenities on Bayview, this commercial space is an ideal setting. Don't miss this exceptional opportunity!

1618 Bayview Avenue W Unit B, Toronto
164 Glenvale Boulevard, Toronto
$2,150,000
3 Beds ⋅ 3 Baths ⋅ C14091094 MLS
Enjoy the Best of Leaside Living. Experience the space, comfort and lifestyle that make Leaside such a sought-after Toronto neighbourhood. Enjoy open, inviting living spaces, with the added flexibility of an extra kitchen, ideal for extended family, entertaining or working from home. Recent renovations add valuable living space and versatility to suit your needs. Outside, a generous, private backyard provides a peaceful retreat, complemented by convenient private driveway parking. Just steps from the Sunnybrook trail network, enjoy easy access to scenic walking and cycling routes, connecting you to nature right from your doorstep. A wonderful opportunity to enjoy the best of Leaside living, where neighbourhood charm, everyday convenience and outdoor recreation come together.

164 Glenvale Boulevard, Toronto
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