LEaside

Leaside is one of Toronto’s most established and desirable neighbourhoods, known for its tree-lined streets, top-ranked schools, beautiful family homes, and strong community feel. From luxury custom homes and renovated detached properties to boutique condos and family-friendly streets near Bayview Avenue, Leaside offers a highly sought-after lifestyle in Midtown Toronto. The Chantel Crisp Real Estate Team provides strategic real estate guidance throughout Leaside, helping buyers and sellers navigate the market with thoughtful preparation, local expertise, data-driven pricing strategies, and concierge-style support.

Top Schools in Leaside

Elementary:

  • Bessborough Drive Elementary & Middle School: 9.9 Fraser Score
  • St. Anselm Catholic School: 8.7 Fraser Score
  • Northlea Elementary & Middle School: 7.8 Fraser Score
  • Rolph Road Elementary School: 7.6 Fraser Score
  • Bennington Heights Elementary School: EQAO Results: Reading - 95%, Writing - 89%, Math - 74%

Secondary:

  • Leaside High School: 9.1 Fraser Score

Private:

  • Blyth Academy: Grades 4-12
  • The York School: Grades JK -12

Homes For Sale In Leaside + Bennington Heights

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  • House in Toronto

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    Main Photo: House in Toronto
    Residential Freehold
    Chantel Crisp
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  • 178 Hanna Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13796982

    178 Hanna Road Leaside Toronto M4G 2N8
    Main Photo: 178 Hanna Road in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13796982
    $1,995,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13796982
    Bedrooms:
    3
    Bathrooms:
    2
    Welcome to 178 Hanna Road, a charming and fully updated 3-bedroom, 2-bathroom detached home in highly sought-after South Leaside, where classic Leaside character, modern comfort, and an incredible private backyard come together to create the perfect setting for family life. From the moment you arrive, the home feels warm and inviting, with bright, beautifully updated interiors and comfortable living spaces designed for everything from quiet evenings at home to gathering with family and friends. Three well-proportioned bedrooms provide plenty of space for a growing family, while the thoughtful updates throughout make this a truly move-in-ready home. Step outside and the experience continues into an incredibly private, professionally landscaped backyard that feels like a hidden urban retreat in the heart of Toronto. Two large decks create multiple spaces for outdoor dining, entertaining, and relaxing, while low-maintenance turf, a full irrigation system, and landscape lighting on a timer make the grounds as effortless to enjoy as they are beautiful, day or night. A professional dog run and dedicated storage she dare discreetly positioned at the rear of the backyard, adding functionality while preserving the beauty and privacy of the outdoor space. And then there is the location. Living at 178Hanna Road means enjoying the quintessential South Leaside lifestyle, where tree-lined streets, top-ranking schools, neighbourhood parks, recreation, and a strong sense of community are all part of everyday life. Just a short stroll away, Bayview Avenue brings some of Toronto's most popular shops, cafes, bakeries, restaurants, and everyday conveniences right to your doorstep, while nearby transit provides easy access throughout the city. It is this combination that makes homes for sale in South Leaside so sought after, and 178 Hanna Road captures it beautifully. This is more than a house in Leaside, it is a place to put down roots, make memories, and call home for years to come. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Chantel Crisp
  • 10 Field Avenue in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13791774

    10 Field Avenue Leaside Toronto M4G 1Y6
    Main Photo: 10 Field Avenue in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13791774
    $4,800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13791774
    Bedrooms:
    5
    Bathrooms:
    5
    Welcome to 10 Field Ave. Primely located in the heart of South Leaside this rare offering is steps to Bessborough P.S & St. Anselms. 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. A retreat in the city. 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 cupboards. A classic center hall layout with a formal Dining & Living room. The Primary suite is very spacious with a gas fireplace, "his and hers" ensuites (new 2026) & 2 walkin closets. The bedrooms are generoulsy sized. 2nd floor laundry room. Kids can kick off their boots 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 a TON of storage & great parking! A sunny turnkey home on a premium double lot! More details
    Listed by RE/MAX ULTIMATE REALTY INC.
    Chantel Crisp
  • 83 Rumsey Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13790394

    83 Rumsey Road Leaside Toronto M4G 1P1
    Main Photo: 83 Rumsey Road in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13790394
    $1,949,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13790394
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to 83 Rumsey Road, an exceptional semi-detached residence in the heart of South Leaside, offering the scale, sophistication and functionality of a detached home in one of Toronto's most coveted family neighbourhoods.The oversized foyer welcomes you with a generous double closet and exceptional storage. The sun-filled living room overlooks the lush greenery of Trace Manes Park, creating a beautiful sense of space and connection to the outdoors. Centrally positioned, the dining room provides an elegant space and is perfectly suited for both intimate dinners and larger gatherings. The heart of the home is a beautifully designed modern kitchen overlooking the family room, complete with custom built-ins, a gas fireplace and views of the private, low-maintenance backyard. Upstairs, the primary retreat features a private balcony, his-and-hers closets and a luxurious 5-piece spa-inspired ensuite. The second and third bedrooms are bright and spacious, with abundant natural light and beautifully appointed private ensuite bathrooms. A dedicated second-floor laundry adds convenience.The finished lower level offers a spacious recreation room with custom built-ins and a walkout to the backyard, plus a versatile fourth bedroom ideal for guests, a nanny or home office. A laundry rough-in and abundant storage complete the lower level. Perfectly positioned ,steps from Trace Manes Park, splash pad, tennis courts, baseball diamond and the Leaside Library, with the vibrant Bayview Avenue strip just a short walk away. Enjoy cafés, restaurants, boutiques and everyday amenities, alongside ravine trails, TTC access , the LRT and a quick drive to the Bayview Extension, Downtown, DVP and 401. 83 Rumsey Road is a rare opportunity to enjoy refined family living, exceptional space and an enviable South Leaside lifestyle. A real pleasure to show! More details
    Listed by RE/MAX ULTIMATE REALTY INC.
    Chantel Crisp
  • House in Toronto

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    Main Photo: House in Toronto
    Residential Freehold
    Chantel Crisp
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  • 8 Beaufield Avenue in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13787372

    8 Beaufield Avenue Leaside Toronto M4G 3R3
    Main Photo: 8 Beaufield Avenue in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13787372
    $1,399,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13787372
    Bedrooms:
    3
    Bathrooms:
    2
    Welcome to 8 Beaufield Avenue, a charming semi-detached home on a quiet, tree-lined street in coveted North Leaside. Set on a generous 25 x 133.5 ft lot, this beautifully maintained residence offers bright, well-proportioned principal rooms, hardwood floors and an inviting layout with an easy connection to the outdoors. The dining room features a walkout to the rear deck, while the well-appointed kitchen offers ample cabinetry, stainless steel appliances and thoughtful storage. Upstairs are three well-proportioned bedrooms, two with double closets, along with a renovated four-piece family bathroom. The finished lower level provides valuable additional living space with a recreation room and convenient walk-up side entrance to the driveway. Outside, the deep west-facing garden is a true highlight, beautifully landscaped with mature trees and established perennials, complemented by a spacious deck with awning for outdoor dining and entertaining. Ideally situated within an easy walk of Northlea French Immersion, Leaside High School, parks, transit and the shops and restaurants of Bayview Avenue. A wonderful opportunity to enjoy a thoughtfully cared-for home in one of North Leaside's most established neighbourhoods. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Chantel Crisp
  • 39 Brentcliffe Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13786368

    39 Brentcliffe Road Leaside Toronto M4G 3Y4
    Main Photo: 39 Brentcliffe Road in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13786368
    $1,349,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13786368
    Bedrooms:
    3
    Bathrooms:
    2
    Looking for your way into North Leaside? Here it is. A meticulously maintained, beautifully renovated three-bedroom semi with the space and updates you want, in one of Toronto's most sought-after family neighbourhoods. Thoughtfully planned with long-term family living in mind, the home has been updated with quality, longevity and everyday ease in mind. Open-concept living, dining and kitchen spaces flow beautifully together, with a fully renovated kitchen offering loads of storage. Canadian oak hardwood floors, new doors, trim and windows bring a fresh, cohesive feel throughout. Upstairs, three comfortable bedrooms and a beautifully renovated bathroom. Downstairs, a great rec room, home office, full washroom, practical laundry and clever storage nooks. Outside, a private backyard with a very large deck made for summer dinners and kids at play. Detached garage with parking for one, plus room for a second car in front. North Leaside delivers the full package: great neighbours, excellent schools including Northlea Elementary and Leaside High School, Sunnybrook Park, parks and trails, groceries and Costco, with Sunnybrook Hospital and the Eglinton LRT close by. Thoughtfully done. Exceptionally well cared for. Ready for whatever comes next. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    Chantel Crisp
  • 125 35 Brian Peck Crescent in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C13785492

    125 35 Brian Peck Crescent Leaside Toronto M4G 0A5
    Main Photo: 125 35 Brian Peck Crescent in Toronto: Leaside Condo Apartment for sale (Toronto C11)  : MLS®# C13785492
    $849,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C13785492
    Bedrooms:
    2
    Bathrooms:
    2
    Let's start by saying that this magnificent ground level suite DOES NOT back on to the street! Perched above street level with a lush canopy of trees below & across, this exceptional suite offers the privacy & views of an elevated home. Enjoy a spectacular terrace that runs full-length of the condo boasting a professionally landscaped garden creating a peaceful outdoor retreat unlike any other. Offering 1,086 SF of living plus an expansive terrace, this bright and spacious suite features a rare square open-concept layout, allowing you to design the living and dining areas to suit your lifestyle instead of the typical long-narrow condo configuration. Luxury laminate wood-inspired floors flow throughout, while the stylish kitchen boasts stainless steel appliances, abundant cabinetry & a large centre island. The Sellers converted a large ensuite space into an impressive walk-in pantry with custom shelving & coffee station. Natural light pours into every room through oversized windows showcasing tranquil greenspace views. The generous primary bedroom features picture windows, a large walk-in closet and an oversized 3 PC split ensuite with a separate water closet and a shower with a new glass door (2025). A spacious 2nd bdrm and a 4 PC bath with a tub provides comfort for tub worshippers. Recent updates include a new front hall closet door and stylish barn door for the w/in closet. This suite includes tandem parking for two vehicles and a locker. Residents of Scenic enjoy exceptional amenities including a state-of-the-art fitness centre that rivals premium gyms, an indoor pool with outdoor lounging area, kids' playroom, party facilities and more. A playground sits just across the street, while the Eglinton LRT is conveniently located on Eglinton, making commuting effortless. Rarely does a suite combine this much indoor space, extraordinary outdoor living, outstanding amenities and an unbeatable location. Don't miss your opportunity to call Scenic home! More details
    Listed by BOSLEY REAL ESTATE LTD.
    Chantel Crisp
  • 3 Kenrae Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13784874

    3 Kenrae Road Leaside Toronto M4G 1X9
    Main Photo: 3 Kenrae Road in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13784874
    $999,800
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13784874
    Bedrooms:
    5
    Bathrooms:
    2
    W Leaside. Situated on a prime lot in one of Toronto's most sought-after family neighbourhoods,this exceptional property offers endless possibilities for first-time buyers, downsizers,investors, end users, or builders looking to create their dream home in an unbeatable location.Lovingly maintained with evident pride of ownership, the home features sun-filled living spaces, a functional layout, and a seamless walkout to a private backyard oasis. Surrounded by mature greenery and the soothing sounds of birdsong, this tranquil outdoor retreat is perfect for relaxing, entertaining, or enjoying nature in the city.Ideally located just steps from top-rated schools, parks, boutique shopping, fine dining, and convenient transit, this home offers the perfect blend of lifestyle and location. Move in and enjoy as is, renovate to suit your vision, or build new on this exceptional lot-the possibilities are endless.An added bonus for investors: the property is currently tenanted by a AAA tenant who is willing to stay, providing immediate income potential and flexibility for future plans. A rare opportunity to own in one of Toronto's most desirable neighbourhoods..Mechanical updates - New eavestroughs and downspouts - 2025-roof and skylight - 2024 furnace -2019, humidifier and air conditioning - 2018, fence and deck - 2018, exterior painting 2022. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    Chantel Crisp
  • 9 Cameron Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13784024

    9 Cameron Crescent Leaside Toronto M4G 1Z7
    Main Photo: 9 Cameron Crescent in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13784024
    $1,299,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13784024
    Bedrooms:
    1
    Bathrooms:
    2
    Welcome to this thoughtfully renovated South Leaside bungalow in a prime location and on a premieur street. Here, exceptional functionality meets comfort and energy efficiency. Renovated in 2021 in keeping the charm of old Leaside homes (leaded glass retained thruout), this home features an oversized kitchen w/built-in stainless steel appliances, lots of cabinetry, a pantry, a dedicated work/desk area and a w/out to an intimate garden. The spacious main-floor primary bdrm offers built-in closets, a custom headboard w/integrated sconces & pot lights, and a generous 4-piece ensuite with two sinks, marble counters, abundant storage, retractable closet rods for clothes drying and a separate glass shower finished with marble. The inviting front living room flows into the dining room, while a cozy family room is highlighted by a beautiful custom stained-glass bay window. The versatile lower level is designed for entertaining, featuring a large recreation/TV room, built-in desk, above-grade window, fully equipped wet bar/mini kitchen and two Murphy beds cleverly concealed behind the walls. A spacious laundry room with additional kitchen facilities and cabinetry provides even more functionality. Storage is exceptional, with a large L-shaped storage room under the stairs plus another separate storage room. Energy efficiency was a priority during the renovation. The walls have an insulation rating exceeding that of a new R-2000 home, and following the installation of the combined Polaris boiler and hot water tank in 2022, the home was audited by a Certified Energy Advisor and achieved an impressive EnerGuide rating of 83-comparable to newer built R-2000 homes. See the attached Home Energy Report for full details. A truly well-designed home offering comfort, versatility, abundant storage and impressive energy performance in sought-after South Leaside. Much sought after Bessborugh Dr Elementary and fabulous neighbours, this is a real find! More details
    Listed by BOSLEY REAL ESTATE LTD.
    Chantel Crisp
  • 521 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13783372

    521 Sutherland Drive Leaside Toronto M4G 1K9
    Main Photo: 521 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13783372
    $2,149,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13783372
    Bedrooms:
    4
    Bathrooms:
    2
    Welcome to 521 Sutherland Drive, a beautifully updated and move-in-ready residence in the heart of highly sought-after North Leaside. Offering three bedrooms, two bathrooms and generous principal rooms, this inviting property combines character with a thoughtful layout designed for everyday living and entertaining. The sun-filled living room features a bay window and fireplace, while the separate dining room provides an elegant setting for dinner parties. The well-appointed kitchen flows into a fabulous main-floor family room and breakfast area overlooking the garden, with a walkout to the deck and expansive, low-maintenance backyard. Upstairs are three well-proportioned bedrooms and a beautifully renovated four-piece bathroom with heated floors. The spacious primary bedroom easily accommodates a king-size bed and features impressive wall-to-wall built-in closets, providing exceptional storage. The finished lower level extends the home's versatility with a recreation area and fourth bedroom, ideal for guests, a private home office, or nanny accommodation. A rare heated double-width garage offers exceptional flexibility and is currently configured for both parking and a dedicated gym with a walkout to the back garden. Renovation plans are included with the sale, presenting exciting possibilities to further enhance and expand the property in the future. The location is equally impressive, just steps from the ravine and its beautiful trails, one block from Northlea French Immersion Public School and close to Leaside High School. Enjoy a short stroll to the LRT, Sunnybrook Park, and the shops, cafés, restaurants, and everyday conveniences of Bayview Avenue and Laird Drive. A wonderful opportunity to move in and enjoy now, with outstanding potential for the future. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    Chantel Crisp
  • 27 Cameron Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13778582

    27 Cameron Crescent Leaside Toronto M4G 1Z9
    OPEN HOUSE: Sep 26, 2026
    02:00 PM - 04:00 PM EDT
    Open House on Saturday, September 26, 2026 2:00PM - 4:00PM
    Main Photo: 27 Cameron Crescent in Toronto: Leaside House for sale (Toronto C11)  : MLS®# C13778582
    $2,499,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C13778582
    Bedrooms:
    4
    Bathrooms:
    3
    Nestled on one of South Leaside's premier streets, this beautifully rebuilt 3+1 bedroom detached home offers timeless charm, exceptional family living, and an unbeatable location. Originally built in 1930 and extensively rebuilt in 1994, it blends classic character with modern comfort. The welcoming main level features an open concept living and dining area where a cozy wood-burning fireplace creates the perfect gathering place on chilly evenings. Large windows in both rooms & skylight over the staircase floods this home with natural light contributing to the warmth of this home. At the heart of the home is a chef-inspired kitchen with SS appliances, stone countertops, lots of cupboards and a large island. And it overlooks the spacious eat-in/breakfast area; perfect for on-the-go lunches and informal family dinners. Open to the spacious family rm with a walk-out to the deck & beautifully landscaped, private backyard, this is the ideal setting for entertaining or relaxed family living. And the main flr 2 PC is so useful. Upstairs, the tranquil primary retreat overlooks the lush back garden and features a full wall of closets plus a 4 PC ensuite. The two other bdrms share a second 4 PC bathroom, while the convenient upper-level laundry adds everyday functionality. The versatile lower level adapts to your family's changing needs. Design the expansive open space as a recreation room, playroom, home office, billiards room, or the ultimate home theatre. A separate 4th bdrm and utility room provide added flexibility for guests, teens, or extended family. Families will appreciate being in the highly sought-after Bessborough Dr Public School catchment, with Trace Manes Park and the public library just around the corner. Surrounded by tree-lined streets and close to shops, restaurants, transit, and all the amenities that make Leaside one of Toronto's most desirable neighbourhoods, this exceptional home offers the perfect balance of comfort, convenience, and lasting value. More details
    Listed by BOSLEY REAL ESTATE LTD.
    Chantel Crisp
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Data was last updated September 21, 2026 at 12:15 PM (UTC)
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 the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.