Leaside Real Estate for Sale

31 Listings
Real estate in Leaside includes beautiful and spacious detached homes and condos in a prestigious and desired neighbourhood in midtown Torontothat combines peaceful suburbanliving on tree-lined streets with access to city conveniences and all sought after amenities. Purchasing a house in Leaside will situate you in an ideally located neighbourhood surrounded by plenty of green space including Sunnybrook Park and close to reputable schools. With proximity to public transit routes and plenty of shopping and restaurants at the Leaside Centre and the ever-growing Laird Avenue, Leaside real estate will continue to be in demand within the coming years.
8 Vanderhoof Avenue, Toronto
3+1
BEDS
2
BATHS
$1,599,000
FOR SALE
An exceptional opportunity in the heart of sought-after South Leaside! Offered for the first time since 1989, this generously proportioned detached home sits on an impressive 30 x 135 ft lot, ideally positioned between two beautiful residential streets in the coveted Bessborough School District. Filled with natural light, this inviting home offers a wonderful combination of space, functionality and endless potential. The main floor features a spacious open-concept living and dining area, a separate kitchen with granite countertops and updated appliances, and a charming sunroom overlooking the deep backyard. Upstairs, three generously sized bedrooms provide comfortable family living. The finished lower level, complete with a separate entrance, additional bedroom, bathroom and kitchenette, offers exceptional flexibility for extended family, guests or additional living space. Outdoors, enjoy an expansive backyard with plenty of room for entertaining, gardening and play, complete with a charming insulated summer guest house that offers versatile space for a home office, creative studio or private retreat. A rare private driveway accommodates 2-3 vehicles, while 200-amp electrical service adds further appeal. Enjoy the convenience of being moments from the shops, cafes and restaurants of Bayview Avenue and Leaside Village, excellent schools, beautiful parks, transit and everyday amenities. Lovingly held by the same owner for over 35 years, this home presents exceptional value in one of Toronto's most desirable family neighbourhoods. Move in, add your personal touches and bring your vision to life in this wonderful South Leaside setting!
797 Millwood Road, Toronto
3+2
BEDS
5
BATHS
$3,899,000
FOR SALE
An architectural masterpiece where striking design, exceptional craftsmanship and effortless living come together in a truly extraordinary home. A showstopper from the moment you arrive, this remarkable custom residence balances dramatic architectural elements with an inviting warmth that makes every space feel like home. Soaring ceilings, skylights, floating stairs, custom millwork and a spectacular open-to-above dining area create an atmosphere of understated sophistication. The stunning kitchen features porcelain countertops, Miele appliances, a pot filler and breakfast bar, flowing seamlessly into beautifully appointed living spaces. A striking fireplace, custom built-ins and bespoke bar set the stage for intimate evenings and memorable gatherings. The primary suite is a private sanctuary with vaulted ceilings, skylight, custom walk-in closets, balcony and spa-inspired ensuite. Thoughtfully designed bedrooms, luxurious bathrooms and a versatile office offer exceptional comfort. Control4 smart home automation, integrated lighting and sound, heated floors, heated driveway and stairs, and Tesla charging deliver effortless everyday living. The finished lower level features a recreation area, kitchen, bathroom and versatile office or potential bedroom with walkout access. Rooftop access reveals two expansive terrace areas, adding another intriguing dimension to this remarkable property. Nestled in coveted Leaside, moments from Bayview Avenue's boutiques, cafés and restaurants, excellent schools, parks and the Eglinton LRT. A rare opportunity to experience architectural distinction, modern convenience and the tranquility of a cherished neighbourhood. More than a beautiful house, this is an extraordinary place to call home.
38 Killdeer Crescent, Toronto
3+1
BEDS
3
BATHS
$3,650,000
FOR SALE
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.
7 Lumley Avenue, Toronto
4+1
BEDS
7
BATHS
$6,595,000
FOR SALE
A stunning, brand new modern home in Bennington Heights, thoughtfully designed with a focus on light, proportion, and practical family living. Set on an impressive 59 ft frontage with a rare circular drive, this home offers a commanding presence from the street. Clean lines and a neutral palette with gorgeous white oak herringbone floors define the aesthetic. This well-executed home offers over 6,200 sq ft of finished living space with impressive design details throughout. A dramatic 21-ft skylit entry introduces the home, anchored by a sculptural open riser staircase. The main floor offers 11 ft ceilings with defined principal rooms through a connected, open flow. Expansive rear windows bring in natural light and create a seamless connection to the backyard. The kitchen is beautifully appointed, centred on a large marble island with integrated appliances and refined finishes, opening to bright breakfast area and pool-sized garden. The adjoining family room features a wood-burning fireplace and oversized windows, creating a warm and comfortable gathering space. Private main floor office and well-designed mudroom with custom cabinetry and side entry add everyday practicality. Street-facing windows are smart windows with automated privacy shading. Upstairs, an open gallery overlooks the level below. All four bedrooms include walk-in closets and private ensuites. The primary suite is set apart with treetop views, a private balcony, a walk-in dressing room, and a spa-inspired ensuite with freestanding tub, glass shower, and dual vanities. A second floor laundry room adds convenience. Lower level offers a walk-up with a separate entrance to a self-contained in-law/nanny suite, along with a large recreation area, home gym, sauna, and glass-enclosed wine room, along with a second laundry room. This is a wonderful and rare opportunity to own a thoughtfully designed home that delivers on scale, quality, and long-term livability.
10 Red Oaks Crescent, Toronto
3+1
BEDS
3
BATHS
$3,250,000
FOR SALE
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.
770 Eglinton Avenue, Toronto
3+1
BEDS
2
BATHS
$1,199,000
FOR SALE
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.
122 Brentcliffe Road, Toronto
3+2
BEDS
4
BATHS
$2,299,000
FOR SALE
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.
663 Eglinton Avenue, Toronto
3+1
BEDS
3
BATHS
$1,372,500
FOR SALE
Fabulous opportunity to own a well-priced, detached home in prestigious Leaside! 3+1 bedrooms, 3 full baths, one on each level. Generous-sized living & dining rooms. Beautifully renovated kitchen. Main floor family room addition with walkout to large deck, 3-pc bath. Gleaming floors. Spacious backyard with interlocking patio & mature trees. 2nd floor bath features an extra-large, glass enclosed shower, modern designer-look vessel sink. Hall linen closet. Main staircase has glass railing. Spacious finished basement offers more living space. Features wainscoting, French doors, built-in shelves. 4th bedroom. 4-pc bath with vessel sink. Walk up from basement to backyard. Wide, interlocking private driveway. Property backs onto highly ranked Leaside High School and Howard Talbot Park. Short walk to new Leaside-Eglinton LRT station at Bayview, 5-minute ride to Yonge St. This high demand neighbourhood offers great shops, cafes, schools in a well-established central Toronto location.
112 Southvale Drive, Toronto
4+1
BEDS
3
BATHS
$2,175,000
FOR SALE
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!
442 Heath Street, Toronto
4+1
BEDS
5
BATHS
$9,495,000
FOR SALE
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.
32 Evergreen Gardens, Toronto
3+1
BEDS
4
BATHS
$2,798,000
FOR SALE
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 Sat November 14th 2.00 to 4.00 PM
10 Field Avenue, Toronto
4+1
BEDS
5
BATHS
$4,499,000
FOR SALE
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.!
164 Glenvale Boulevard, Toronto
3
BEDS
3
BATHS
$2,150,000
FOR SALE
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.
136 Glenvale Boulevard, Toronto
3+1
BEDS
2
BATHS
$1,499,000
FOR SALE
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.
817 Millwood Road, Toronto
3
BEDS
3
BATHS
$1,949,000
FOR SALE
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.
127 Glenvale Boulevard, Toronto
3+1
BEDS
4
BATHS
$2,088,000
FOR SALE
Welcome to a home ( Legal Duplex) where thoughtful design meets elevated living. A beautiful transformed three-bedroom semi that blends luxury, functionality and investment potential. Completely renovated from top to bottom, this home showcases sleek contemporary design, high-end materials and a layout crafted for modern living. The " SEPARATE METERED legal basement suite" is finished to the same high standard, making it perfect for extended family, guests or a strong income stream, or use it as part of their house. With refined styling, efficient use of space, and premium upgrades throughout, this property is the perfect balance between personal comfort and smart real estate investing. Hybrid HVAC furnace + heat pump, foam insulation, including attic, sound proof insulation on wall with adjacent neighbour, concrete in-ground pool w/safety enclosure, wall-to-wall storage in all three second upper floor bedrooms, hidden prep kitchen and pantry. Artificial turf backyard, over 120 sq/ft of attic storage, too many upgrades and features to list. A pleasure to show.
551 Broadway Avenue, Toronto
3
BEDS
5
BATHS
$3,899,000
FOR SALE
Exceptional Custom-Built Luxury Home In Prestigious North Leaside! Completed In 2024, This Stunning Approx. 3,000 Sq. Ft. Detached Residence Showcases Contemporary Architecture, Sophisticated Design And Outstanding Craftsmanship. Located In A Highly Desirable Neighbourhood, This Home Offers Modern Elegance And Exceptional Comfort. The Spectacular Open-Concept Main Floor Features Soaring 11-Ft Ceilings, Floor-To-Ceiling European Aluminum Windows And An Abundance Of Natural Light, Enhanced By 7 Skylights Throughout. Premium European Engineered Hardwood Flooring Extends Across The Main And Second Levels. A Stylish Private Office With Custom Wood And Glass Doors Provides An Ideal Workspace, While The Living And Dining Areas Feature Striking Custom 3D Fireplaces And Designer Wall Units. The Gourmet Kitchen Boasts Sleek Carbon Cabinetry And Premium JennAir Appliances, Including A 6-Burner Gas Stove And Built-In Oven. Upstairs, Four Spacious Bedrooms Offer Bright, Inviting Living Spaces. The Luxurious Primary Suite Features A Boutique-Style Walk-In Closet And Spa-Inspired 5-Piece Ensuite With Heated Floors. Skylights Illuminate The Upper-Level Bathrooms And Closets. The Beautifully Finished Walk-Up Lower Level Is An Entertainer's Dream, Featuring Heated Floors, A Custom 100-Bottle Wine Display, Elegant Wet Bar With Accent Lighting And Built-In Wine Fridge. Additional Highlights Include Heated Foyer And Bathroom Floors, Exquisite Designer Tilework And Exceptional Attention To Detail. Conveniently Located Near Excellent Schools, Parks, Shopping And Amenities. A Rare Opportunity To Own A Modern Architectural Gem In One Of Toronto's Most Sought-After Neighbourhoods!
48 Sharron Drive, Toronto
4+1
BEDS
4
BATHS
$3,449,000
FOR SALE
Stunning Custom-Built Residence In The Highly Sought-After Bessborough School District! Steps To The Vibrant Shops, Restaurants And Cafés Along Bayview Avenue, With Convenient Access To Public Transit And Major Highways. Offering Approximately 3,400 Sq. Ft. Of Beautifully Designed Living Space, Including A Lower-Level Nanny Suite With A Separate Entrance, Full Kitchen And Spacious Recreation Room. Thoughtfully Designed Open-Concept Main Floor With Soaring 10-Ft Ceilings, Perfect For Everyday Living And Entertaining. Gourmet Kitchen Featuring An Impressive 11-Ft Island. Expansive Floor-To-Ceiling Windows Flood The Home With Natural Light. Generously Sized Bedrooms With Custom Closet Organizers, Including A Luxurious Primary Retreat With A Spa-Inspired Ensuite Featuring An Oversized Shower With Massage Jets. Fourth Bedroom Features Custom Office Built-Ins, Ideal For Working From Home. Abundant Storage Throughout, Including A Spacious Mudroom And Large Garage Storage Loft. Built-In Garage Plus A Private Driveway Accommodating Up To Three Additional Vehicles. Smart Home Features, Two Full Kitchens And Two Laundry Rooms Offer Exceptional Convenience And Flexibility. A Rare Opportunity To Enjoy Modern Comfort, Thoughtful Design And Exceptional Functionality In The Heart Of Leaside!
15 Moorehill Drive, Toronto
5+1
BEDS
4
BATHS
$3,900,000
FOR SALE
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.
4 Douglas Crescent, Toronto
4+1
BEDS
5
BATHS
$4,999,000
FOR SALE
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.
1801 Bayview Avenue 103, Toronto
1
BEDS
1
BATHS
$459,000
FOR SALE
Welcome to Suite 103 at 1801 Bayview Avenue! Situated in sought-after Leaside, this bright and well-appointed ground-floor suite offers exceptional value and convenience. The thoughtfully designed layout features full-sized appliances, a generously sized bedroom, and a walkout to your own private terrace, creating a seamless extension of the living space. Complete with a dedicated parking space and storage locker, residents also enjoy an array of shared amenities, including a fitness facility, party room, and on-site concierge.Ideally located at Bayview and Eglinton, enjoy an abundance of amenities just steps from your door, including public transit, grocery stores, restaurants, shops, parks, and more. Offering a great combination of space, convenience, and value, Suite 103 is an excellent opportunity in one of Toronto's most desirable neighbourhoods.
45 Mcrae Drive, Toronto
3+1
BEDS
2
BATHS
$1,995,000
FOR SALE
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.
319 Rumsey Road, Toronto
4
BEDS
4
BATHS
$3,589,000
FOR SALE
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!
25 Malcolm Road 308, Toronto
2
BEDS
1
BATHS
$645,000
FOR SALE
Bright, stylish, and thoughtfully laid out, this 701 sq. ft. 2-bedroom, 1-bathroom condo puts you right in the heart of Leaside, one of Toronto's most desirable neighbourhoods. With a sensible floor plan, south-facing exposure, charming balcony, and plenty of natural light, this is a home that makes the most of every square foot. Enjoy open-concept living and dining area while the second bedroom offers incredible flexibility - use it as a comfortable bedroom, home office, guest space, or whatever suits your lifestyle. The kitchen features a long island with plenty of room for prep, dining, and gathering, making it the natural hub of the home. Enjoy everything Leaside has to offer with an abundance of shops, restaurants, cafés, groceries, schools, community amenities, and everyday conveniences right at your doorstep. Transit is also easily accessible, including the Eglinton LRT, while quick access to the Bayview Extension and Don Valley makes getting around the city by car a breeze. Enjoy an impressive collection of building amenities including a beautiful rooftop terrace with BBQs, fitness centre, concierge, pet-friendly facilities including a dog spa, and secure underground parking. Add in a wide parking space and a welcoming community of neighbours, and you have a building that truly feels like home. Whether you're a first-time buyer, downsizer, investor, or simply looking for a well-connected home in Leaside, this one checks all the boxes. Move in, settle in, and start enjoying everything this vibrant neighbourhood has to offer.
178 Hanna Road, Toronto
3
BEDS
2
BATHS
$1,895,000
FOR SALE
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.
431 Heath Street, Toronto
4+1
BEDS
6
BATHS
$5,949,000
FOR SALE
A Masterpiece Like No Other - A Rare Custom-Built Marvel. Introducing a truly one-of-a-kind, never-before-seen or lived in custom-built home that redefines modern luxury living. Designed and constructed with uncompromising precision for the builder himself, every inch of this residence exudes meticulous craftsmanship, innovative design, and elite attention to detail. From the moment you step inside, you're greeted with soaring ceilings, architectural elements rarely found in today's market, and oversized, floor-to-ceiling windows that flood the home with natural light and create a seamless connection between indoor and outdoor living. No expense was spared - from the exquisite millwork and high-end designer finishes to the flawless flow of the layout, every feature has been hand-selected and customized to perfection. This is not just a home - it's a statement. Built to be lived in and loved by its creator, the opportunity to own this level of excellence is extremely rare. What's been created here has never existed in this area and likely never will again. Immaculate. Timeless. Unrepeatable. Don't miss your chance to experience a home that sets a new benchmark for what's possible.POOL PERMIT HAS BEEN ACCEPTED!
1801 Bayview Avenue Ph 802, Toronto
2+1
BEDS
2
BATHS
$899,000
FOR SALE
A rare 2-storey Leaside Penthouse that lives like a house - 1,230 SQ. FT. + south terrace + 2 side-by-side parking. Maintenance fee is ALL INCLUSIVE. No additional utility bills! Perched above it all, this sophisticated penthouse of beautifully updated living space plus a 101 sq ft south facing terrace, with dramatic double height ceilings, and an airy, open feel. The flexible 2+1 bedroom, 2-bathroom (one on each level) layout effortlessly balances style, comfort and functionality. Currently configured with both living and family rooms, the main level offers exceptional versatility, with the family room easily enclosed to create a second bedroom. At the heart of the home is a stunning designer kitchen, renovated in 2023 with quartz counters and thoughtfully designed for both everyday living and entertaining. A statement spiral staircase leads to the upper level, with an expansive primary retreat. French doors from the bedroom open up to a separate office or sitting area, while a designer bathroom and two walk-in closets complete this impressive suite. Numerous additional upgrades include two beautifully updated full bathrooms, engineered hardwood flooring, custom storage, full size laundry with plenty of storage, new heat pump (2026), electric fireplace, and refined finishes throughout. Includes- 2 Parking spots (side by side) & a locker in a well managed, updated mid size building with 81 units. Building amenities incl Concierge Mon- Fri 9-5pm, a Guest Suite, 20 Visitor parking spots, Meeting Room, Party Room, Exercise Room & Bike Storage. Spacious, stylish and exceptionally versatile, this unique penthouse offers the feel of a home with the ease of condominium living-all in an incredibly convenient location just steps to the LRT and minutes from the shops, restaurants, parks and amenities that make Leaside such a sought-after neighbourhood.
40 Divadale Drive, Toronto
4+1
BEDS
5
BATHS
$3,999,999
FOR SALE
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.
1387 Bayview Avenue 306, Toronto
1+1
BEDS
1
BATHS
$399,000
FOR SALE
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!!!
1901 Bayview Avenue 106, Toronto
1
BEDS
1
BATHS
$399,000
FOR SALE
**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!
354 Bessborough Drive, Toronto
4+2
BEDS
5
BATHS
$3,299,999
FOR SALE
Welcome home to this beautifully renovated 2-storey residence in the heart of Leaside - one of Toronto's most sought-after family neighborhoods. This 4+2 bedroom, 5 bathroom home blends modern style with everyday function, offering the perfect move-in-ready package for growing families. Completely renovated in 2025, the property boasts premium updates including a modern kitchen equipped with top-of-the-line KitchenAid and Miele appliances. Enjoy beautiful hardwood floors throughout, enhanced by the warmth of four gas fireplaces creating cozy living spaces. The home features two convenient laundry rooms, a new roof 2025, ensuring comfort and peace of mind. Step inside to find sun-filled principal rooms, sleek contemporary finishes, and thoughtful upgrades throughout, creating a space that feels both polished and welcoming. Upstairs, four generous bedrooms and beautifully appointed bathrooms provide comfortable, private space for the whole family. Basement creates the perfect space for extended family, in-laws or nanny quaters - whatever your family needs. Then you can Relax, unwind, and get lost in your backyard oasis where everyday feels like a getaway.Perfectly positioned just steps to Leaside's charming shops and cafés, with easy access to TTC transit, this home is also close to top-rated schools and Sunnybrook, plus nearby parks and green space for outdoor enthusiasts. A rare opportunity to own a fully renovated home in one of Leaside's best pockets - luxury, location, and lifestyle all in one.
DIALOG CONTENT
Would you like to receive Similar Listing Alerts as soon as they are uploaded to MLS®?
How would you rate our website?
★
★
★
★
★
Would you like to rate us on Google?
Yes
488673740