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.
Homes For Sale In Leaside + Bennington Heights
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40 Divadale Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13754186
40 Divadale Drive Toronto M4G 2N9 
$3,999,999Residential Freehold- Status:
- Active
- MLS® Num:
- C13754186
- Bedrooms:
- 5
- Bathrooms:
- 5
Welcome to an exceptional custom residence in the heart of coveted North Leaside. Impeccably designed with refined craftsmanship, sophisticated finishes, and an effortless sense of luxury, this remarkable home is perfectly suited to both elegant entertaining and comfortable family living. An impressive array of premium features include heated basement floors, a private sauna and hot tub, sophisticated wet bar and wine cellar, custom cabinetry, rich walnut flooring and top-of-the-line appliances. Every element has been thoughtfully curated to create a residence of exceptional quality and distinction. Ideally positioned just steps from the Crosstown LRT, highly regarded schools, boutique shop, acclaimed restaurants, parks and Sunnybrook Hospital. This is a rare opportunity to enjoy the very best of North Leaside living. Simply move in, settle in, and experience a home where luxury, lifestyle and location come together effortlessly. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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553 Broadway Avenue in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13753904
553 Broadway Avenue Toronto M4G 2S2
$3,550,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13753904
- Bedrooms:
- 5
- Bathrooms:
- 5
This Leaside jewel has serious attention to detail everywhere you look. Classic finishes with design elements well integrated throughout the entire home create an elegant, serene flow from one exquisite space to the next. Ebony hardwood floors greet you on entry through the front living room and formal dining room. The gourmet kitchen with breakfast bar is combined with a family room which features a built-in entertainment wall, and there is also a casual dining area overlooking the walkout sundeck and stunning south facing landscaped yard. On the second floor the primary bedroom features soaring ceilings, a Juliet balcony, 6 piece ensuite with steam shower and a generous walk-in closet. There are also three more large bedrooms (all with ensuites) and convenient second floor laundry. The lower level is expansive and bright, with nine foot ceilings, a massive recreation room with a gas fireplace, walk-out to the yard and in-law/nanny suite optionality. As you walk through, it just feels like home. Not to be missed. More detailsListed by REAL ESTATE HOMEWARD- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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136 Glenvale Boulevard in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13753894
136 Glenvale Boulevard Toronto M4G 2V9 OPEN HOUSE: Sep 12, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 12, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 13, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 13, 2026 2:00PM - 4:00PM
$1,699,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13753894
- Bedrooms:
- 4
- Bathrooms:
- 2
Welcome to North Leaside living at its finest! This exceptional extra-wide semi-detached home has been beautifully renovated and thoughtfully expanded, offering nearly 2,000 sq. ft. of stylish living space, including a spacious rear addition and desirable third bedroom.Enjoy a brand-new kitchen with stainless steel appliances, new hardwood flooring throughout, and all-new windows. The bright, versatile layout is perfect for modern family living and entertaining.Outside, a private and spacious garden creates the perfect setting for summer BBQs and relaxation, complemented by a large storage shed. A rare private driveway with parking for up to 4 cars adds incredible convenience.Ideally located just steps from Northlea Public School with English & French Immersion programs, and minutes to Eglinton TTC, Leaside subway & LRT stations, Serena Gundy Park and Sunnybrook Dog Park.A rare opportunity to own a beautifully updated, move-in-ready home in one of North Leaside's most sought-after neighbourhoods. More detailsListed by RE/MAX REALTRON TNS REALTY INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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201 60 Aerodrome Crescent in Toronto: Leaside Condo Townhouse for sale (Toronto C11) : MLS®# C13753362
201 60 Aerodrome Crescent Toronto M4G 4J1 OPEN HOUSE: Sep 12, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 12, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 13, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 13, 2026 2:00PM - 4:00PM
$749,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C13753362
- Bedrooms:
- 2
- Bathrooms:
- 2
Freshly painted and thoughtfully maintained, this bright 2-bedroom, 2-bath stacked townhome offers an easy, comfortable way to enjoy Leaside living. The open-concept living, dining, and kitchen area is filled with natural light and works just as well for a quiet night in as it does for hosting friends.The primary bedroom includes a private ensuite, dual closets, and a walk-out balcony overlooking greenery-an ideal spot for a morning coffee or a little fresh air at the end of the day. Underground parking add everyday convenience, while the well-managed building also offers visitor parking. Set in a quiet, family-friendly pocket of Leaside, you're close to transit, neighbourhood shops, restaurants, parks, playgrounds, and highly regarded schools in the Bennington Heights/Leaside High School district. Flemingdon Park Golf Club, Edwards Gardens, Sunnybrook Park, and Sunnybrook Hospital are all nearby. With the Laird Station on the Eglinton Crosstown LRT and quick DVP access makes trips downtown straightforward. A lovely option for first-time buyers, downsizers, or anyone looking for a well-kept home in a connected neighbourhood. More detailsListed by INTERNATIONAL REALTY FIRM, INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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32 Evergreen Gardens in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13752418
32 Evergreen Gardens Toronto M4G 1C5 OPEN HOUSE: Sep 12, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 12, 2026 2:00PM - 4:00PM
$2,898,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13752418
- Bedrooms:
- 5
- Bathrooms:
- 4
Bennington Heights - A complete home composed vertically - incomparable value for more than 4,000 square feet with 20-foot-wide interior living space across four levels of thoughtfully designed luxury, plus an expansive, south-facing, finished rooftop terrace. Built to the highest standard of workmanship by a reputable, award-winning team of architects, interior designers, and builders, this exceptional residence offers a seamless blend of modern elegance and timeless design.Private elevator access serves all five levels, along with the peace of mind of a full Tarion warranty. Distinctive features include a ground-floor bedroom or family room with a three-piece bathroom, and a main floor with soaring ceilings and floor-to-ceiling windows that flood the home with natural light. Spacious principal rooms and a modern custom chef's kitchen with a centre island and integrated breakfast table complete the main level. White oak and painted cabinetry, veined marble counters, and high-quality appliances are found throughout. The kitchen walks out to a balcony with a BBQ gas line - perfect for indoor-outdoor living.Additional highlights include white oak engineered hardwood floors, custom millwork and doors, a linear fireplace, and spa-inspired bathrooms finished in marble and porcelain. Ample built-in storage and thoughtfully designed cabinetry are found on every level. The home offers two-car parking with a built-in single garage and private front driveway, along with a landscaped backyard and patio. An unobstructed, 800-square-foot, south-facing rooftop terrace features a built-in pergola and Corten steel garden beds - ideal for sunbathing, entertaining, or relaxing under the stars. Enjoy immediate access to the Kay Gardner Belt line Trail, Don River Valley trails, and Evergreen Brick Works, with Bayview shops and Evergreen Gardens Park close by, and quick downtown access via the Bayview Extension and Don Valley Parkway. Open House September 12th Saturday 2 to 4 More detailsListed by HARVEY KALLES REAL ESTATE LTD.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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3 Thursfield Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13752072
3 Thursfield Crescent Toronto M4G 2N4 OPEN HOUSE: Sep 12, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 12, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 13, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 13, 2026 2:00PM - 4:00PM
$1,349,999Residential Freehold- Status:
- Active
- MLS® Num:
- C13752072
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to 3 Thursfield Crescent, a beautifully renovated semi-detached home on a family-friendly street in the heart of North Leaside. Fully renovated in 2019, including new insulation, engineered hardwood and extensive updates throughout, this home offers a thoughtful layout, generous principal rooms, a spectacular deep lot and detached garage. A welcoming foyer with generous closet space opens to an oversized living room with plenty of space to relax and entertain. At the heart of the home, the renovated kitchen features abundant cabinetry, stainless steel appliances and a breakfast bar overlooking the dining area. The bright dining room is framed by beautiful views of the expansive backyard and features custom built-in cabinetry and a charming built-in bench. Walk out directly from the kitchen to the large rear deck, creating a seamless extension of the living space and the perfect setting for outdoor dining and summer entertaining. Upstairs, three well-proportioned bedrooms include a spacious primary retreat with wall-to-wall closets and ample room for a king-sized bed. A 4-piece bathroom and linen closet complete the second floor. The lower level adds valuable living space with a recreation room featuring high ceilings and built-in cabinetry, plus a convenient 3-piece bathroom. A highly functional laundry room offers oversized machines, extensive cabinetry, a utility sink and generous counter space. The spectacular backyard is the true showstopper, featuring a large deck, multiple areas for dining and entertaining, plenty of grass and room to play. The detached garage provides secure parking and additional storage. Just steps from Sunnybrook Park, with shops, restaurants, cafés and everyday amenities nearby. Enjoy convenient access to the Eglinton Crosstown LRT, TTC and DVP. A rare opportunity to enjoy a fully renovated home, exceptional outdoor space and the best of North Leaside living. More detailsListed by RE/MAX ULTIMATE REALTY INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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112 Southvale Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13738186
112 Southvale Drive Toronto M4G 1G7
$2,349,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13738186
- Bedrooms:
- 5
- Bathrooms:
- 3
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! More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEA- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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181 Rumsey Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13737624
181 Rumsey Road Toronto M4G 1P4
$2,695,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13737624
- Bedrooms:
- 5
- Bathrooms:
- 4
Custom built and well-designed home that captures timeless contemporary architecture and a floor plan designed for versatile family living. Situated on a prime 33' x 134' lot in the heart of Leaside. Modern interiors, 9 foot ceilings and hardwood floors on main & second floor, clean architectural lines, and minimalist trim. Spacious living & dining room are anchored by a wood burning fireplace. Designed for everyday family living & entertaining, the kitchen has shaker style maple cabinetry, oversized island topped in Quartz that seats 6, breakfast area, spacious built-in desk functions as an office nook/homework station. Family room with a wall of windows, gas fireplace, custom built-ins, powder room and walk out to the garden. Second floor is highlighted by a large skylight, a custom wood staircase with adonized aluminum detailing. Spacious primary suite features a wall of windows, sitting area, and a 4 piece ensuite, separate shower and soaker tub. Three additional well-proportioned bedrooms with excellent closet space & a large 4 piece bathroom. Lower level was designed to provide exceptional versatility with changing family dynamics in mind. Currently used as an extension of the family's living space, it can function as a fully self-contained suite; ideal for extended family, a young adult transitioning toward independent living while remaining home, live-in nanny, or income producing suite. Features: living/dining, full kitchen, separate entrance, bedroom with large windows, and three piece bath; or use the space as the current owner does-recreation room with kitchen for entertaining. Fully fenced garden with flagstone patio, perennial plantings, & garden shed with brick detailing/contemporary horizontal wood. Exceptional walkability to Bayview and Laird amenities, Leaside LRT stop, school catchment area of Bessborough Elemen & Middle, Leaside High, St. Anselm Catholic. A home that combines exceptional design, generous living space, and an enviable location. More detailsListed by Johnston & Daniel and ROYAL LEPAGE/J & D DIVISION- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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306 1387 Bayview Avenue in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C13731462
306 1387 Bayview Avenue Toronto M4G 3A5
$399,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C13731462
- Bedrooms:
- 2
- Bathrooms:
- 1
Welcome to SAHIL. Stay At Home In Leaside is a unique boutique building In One Of The Most Desirable Neighbourhoods In Toronto! and a Life Lease for seniors 60 And Over, Very Well Maintained by A Professional Property Management Company And With A Healthy Reserve Fund To Pay For Future Repairs And Replacements. This Immaculate 1+1 unit, South facing with walkout to balcony. Property is vacant and Move in ready!!! Enjoy the lifestyle and amenities of beautiful Leaside at a very affordable price!!!. High walkability Score. Steps To All The shops and amenities, A Big Advantage To Life Lease Is THERE IS NO LAND TRANSFER TAX!!! Monthly Maintenance Fees And Taxes Are Considerably Lower Than Comparable Buildings In The Neighbouring Areas! Just Pay Your Own Hydro, Gas And CATV, Most Everything Else Is Included! Building Features Include Lounge, Outdoor Patio With BBQ, Workshop. Buyers Buy The Right To Occupy The Unit And Pay A Monthly Maintenance Fee Up Until The Time They Decide To Sell! (Please See Attached). Don't Miss this One!!! More detailsListed by RIGHT AT HOME REALTY- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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391 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13728200
391 Sutherland Drive Toronto M4G 1K1
$1,349,900Residential Freehold- Status:
- Active
- MLS® Num:
- C13728200
- Bedrooms:
- 3
- Bathrooms:
- 1
Leaside Detached Opportunity!! Well located detached home in Prime South/Central Leaside, just steps to the new Laird LRT station. Perfect opportunity to put your personal stamp on this property, let your imagination turn this Leaside classic into your custom creation. The home is filled with original character, including classic crown mouldings, hardwood floors and a warm wood burning fireplace in the living room. Enjoy the spacious formal living and dining rooms, ideal for entertaining and family celebrations. There's good height in the basement, and space to update and create extra living space. The furnace has been upgraded to an Indirect Hot Water Heater recently, along with drains from the house to city line. Ideally located in Central Leaside, an easy walk to numerous quality local schools.. Bessborough PS (JK-8), Northlea PS (JK-8 for French Immersion), Leaside HS, and St Anselm (JK-8, Catholic) and numerous other private options and preschools. The vibrant commercial areas of both Bayview Ave and Laird Drive just a short walk away....endless restaurants, local pubs, shops, and big box stores. A wide range of local amenities are a close by...Talbot Park, Trace Manes Park, Leaside library, Leaside Tennis Club & other public courts, Leaside Arena and Curling Club, Leaside Pool, and several access points to Serena Gundy/Sunnybrook Park and the expansive Toronto ravine system and trails. Downtown is minutes away via the TTC or Bayview Extension, the DVP just a few lights east, with quick access to both the 401 & Gardiner Expwy. Great opportunity for builders or those wanting to renovate to your personal tastes More detailsListed by ROYAL LEPAGE TERREQUITY REALTY- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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106 1901 Bayview Avenue in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C13694796
106 1901 Bayview Avenue Toronto M4G 3E4
$419,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C13694796
- Bedrooms:
- 1
- Bathrooms:
- 1
**Beautifully Renovated 1-Bedroom Suite in Boutique Mid-Town Building** Welcome to this gorgeous, totally renovated 1-bedroom, 1-bathroom suite in a charming 4-storey boutique building in the heart of mid-town Toronto. The sun-filled living room features freshly painted walls and new flooring throughout, with a separate dining area that is perfect for entertaining. The beautifully updated kitchen offers quartz countertops, built-in appliances and an abundance of prep space. The spacious primary bedroom features a double closet and lovely green views. The spa-like bathroom is crisp, fresh and completely renovated. Enjoy excellent storage throughout the suite, plus the added convenience of a separate locker. Ideally located just steps to the TTC, shopping, Sunnybrook Park and its extensive trails, and some of Toronto's great schools. A truly special suite in a wonderful location - you will not be disappointed! More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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153 Parkhurst Boulevard in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13693184
153 Parkhurst Boulevard Toronto M4G 2E8
$1,488,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13693184
- Bedrooms:
- 4
- Bathrooms:
- 2
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. More detailsListed by Signature Elite Realty Ltd.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
Data was last updated September 8, 2026 at 02:15 PM (UTC)
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