Homes For Sale In Leaside + Bennington Heights
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344 Bessborough Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12872310
344 Bessborough Drive Toronto M4G 3L2 OPEN HOUSE: Mar 14, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, March 14, 2026 2:00PM - 4:00PMOPEN HOUSE: Mar 15, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, March 15, 2026 2:00PM - 4:00PM
$4,199,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12872310
- Bedrooms:
- 5
- Bathrooms:
- 5
The moment you step into 344 Bessborough, you understand why North Leaside commands respect. This is heritage Toronto - the kind of neighbourhood where mature maples line streets that have watched the city grow for a century. And this property? It's the Leaside difference in full. Built in 2013 by Ivey Glenn - a builder known for construction quality over cost-cutting - this home offers 4,741 square feet across three fully finished levels. That number matters. At $4.2M, comparable in Moore Park and Lawrence Park rarely exceed 3,500 square feet. Here, the space is genuine. Main floor ceilings rise to 10 feet. The living and dining rooms flow with proportion and light. The kitchen opens naturally into a generous family room with double walkouts to a 727- square-foot wood deck - not a patio, an outdoor room. Upstairs, the primary suite features a cathedral ceiling, Juliette balcony, and dedicated dressing area. Bedroom 2 has its own ensuite and walk-in closet. Bedroom 3 is oversized. Five bathrooms in total, upper-floor laundry, and space that never forces compromise. The lower level earns the home its versatility. Nearly 1,500 finished square feet with close to 9-foot ceilings, a full second kitchen, bedroom, recreation room, 4-piece bath, dedicated laundry, and a walk-out to the garden. It functions entirely independently - ideal for extended family, live-in help, or guests who prefer their own space. Three gas fireplaces. Two laundry rooms. Attached garage with private drive. TTC transit one minute on foot. Leaside High School in seven. Sherwood Park in five. Sunnybrook less than a kilometre away. More detailsListed by ROYAL LEPAGE TERREQUITY SEYMOUR REAL ESTATE- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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207 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12872010
207 Sutherland Drive Toronto M4G 1J1 OPEN HOUSE: Mar 15, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, March 15, 2026 2:00PM - 4:00PM
$2,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12872010
- Bedrooms:
- 4
- Bathrooms:
- 4
This Showstopper Delivers The True Meaning Of Turnkey Living. Completely Refreshed, Renewed, And Revitalized From Top To Bottom, There Is Truly Nothing Left To Do But Move In And Enjoy. Every Detail Has Been Thoughtfully Upgraded With A Modern Yet Timeless Design. Wide Plank White Oak Flooring Runs Throughout, Anchoring The Home With Warmth And Sophistication, While The Chef's Kitchen Features A Striking Double Waterfall Quartz Island Perfect For Cooking, Entertaining, And Everyday Living. The Main Floor Offers Exceptional Functionality With A Convenient Powder Room And Seamless Flow For Family Life And Entertaining. The Family Room Opens Through A Double Door Slider To The Back Deck, Creating Beautiful Indoor Outdoor Living And Effortless Entertaining. From Inside, It Is Easy To Keep An Eye On Kids Playing In The Large Fenced Backyard, Designed For Both Family Life And Gatherings With Multiple Seating And Entertaining Areas. The Property Also Features A Huge Garage Offering Excellent Storage And Parking. Upstairs, The Spacious Primary Retreat Is A Private Sanctuary Featuring A Stunning Ensuite With Double Vanity And A Walk Through Closet Leading To His And Hers Walk In Closets. Generous Kids Bedrooms Are Paired With A Beautifully Finished High End Family Bathroom Designed For Both Style And Practicality. Thoughtfully Designed For Modern Living, The Home Includes Two Laundry Rooms, One On The Upper Level And One In The Lower Level For Ultimate Convenience. A Side Entrance Leads To A Fully Finished Basement Complete With Its Own Kitchen, Bathroom, Bedroom, Living Area, And Recreation Space. Perfect For Visiting Family, Overnight Guests, A Nanny Suite, In Law Accommodation, Multi Generational Living, Or Potential Rental Income. Homes With This Level Of Care, Upgrades, And Versatility Rarely Come To Market. If You're Searching In This Neighbourhood, This Is One You Simply Cannot Afford To Miss. 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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606 25 Malcolm Road in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12868850
606 25 Malcolm Road Toronto M4G 0C1
$779,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12868850
- Bedrooms:
- 2
- Bathrooms:
- 2
Client RemarksChic Contemporary Residence in the Heart of Leaside. This bright and spacious split bedroom unit features an open-concept layout with floor-to-ceiling windows that flood the space with natural light. It has 9-foot ceilings and engineered hardwood floors. The modern kitchen is equipped with sleek cabinetry, beautiful quartz countertops, premium appliances, and a large island perfect for entertaining. The living area opens to a private 220 sq ft balcony with unobstructed south-facing views, ideal for relaxing or enjoying morning coffee. With generous bedroom space, ample storage, and high-end finishes throughout, this unit is a perfect blend of style and functionality. Located in a boutique mid-rise building that offers a refined living experience with only 60+ units spread across 7 floors. Residents enjoy access to a range of upscale amenities including a fitness centre, rooftop terrace with BBQs, concierge service, and a pet-friendly environment. The building's design emphasizes privacy and luxury, with thoughtfully curated common areas and secure underground parking. You will find amazing neighbours in the building, certainly some of the friendliest in the City. Nestled in the vibrant Leaside community, it is surrounded by an array of local conveniences and lifestyle offerings. Just steps away are charming cafes, gourmet restaurants, and boutique shops along Laird Drive and Bayview Avenue. The area boasts excellent schools, lush parks like Trace Manes Park, and easy access to public transit including the upcoming Eglinton Crosstown LRT. Whether you're looking for a peaceful residential vibe or urban connectivity, this location delivers the best of both worlds. More detailsListed by REAL BROKER ONTARIO LTD.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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702 1801 Bayview Avenue in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12859590
702 1801 Bayview Avenue Toronto M4G 4K2
$698,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12859590
- Bedrooms:
- 2
- Bathrooms:
- 2
Welcome to Suite 702 at 1801 Bayview Avenue - a bright, south-facing residence in the heart of highly desirable Leaside. Filled with natural light, this well-designed suite features an excellent layout with a modern kitchen and breakfast bar, generously sized bedrooms, and the convenience of in-suite laundry. Maintenance fees include all utilities-hydro, heat, water, building insurance, and common elements-offering exceptional value and peace of mind. Perfect for first-time buyers, downsizers, or young families, this boutique condominium rarely becomes available. Located in the coveted Leaside school district, you can walk to Northlea Elementary & Middle School and Leaside High School, making it an ideal home for those who value top-tier education and a strong community atmosphere. Everyday conveniences are right outside your door, with Metro and Tim Hortons directly across the street and the new Eglinton Crosstown LRT just steps away for effortless commuting across the city. Enjoy strolling along Bayview Avenue's vibrant shops, cafés, and restaurants, or take advantage of nearby parks, trails. A rare opportunity to own in one of Toronto's most established and family-friendly neighbourhoods-where location, lifestyle, and convenience come together. More detailsListed by RARE REAL ESTATE- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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127 Glenvale Boulevard in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12858840
127 Glenvale Boulevard Toronto M4G 2W1
$2,199,888Residential Freehold- Status:
- Active
- MLS® Num:
- C12858840
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to a home ( Legal Duplex)_where thoughtful design meets elevated living. a beautifully 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 '' SEPERATE 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 part of eholr 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 e including attic ,sound proof insulations on wall with adjacent neighbor, 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. More detailsListed by HOMELIFE FRONTIER REALTY INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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172 Hanna Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12858772
172 Hanna Road Toronto M4G 3N8
$3,389,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12858772
- Bedrooms:
- 5
- Bathrooms:
- 6
Custom-built classic red brick home designed by Peter Higgins and built by Vaughan Contruction in 2012 features 4+1 bedrooms and 6 bathrooms. The front hallway and mudroom feature heated floors, along with a convenient powder room. The formal living room is highlighted by a fireplace and large windows, flowing seamlessly into the dining room-perfect for entertaining. The spacious kitchen includes stainless steel appliances, quartz counter tops, a large centre island, and a bright breakfast nook. The kitchen is open concept to the the family room with large windows and a walk out to the private back patio. The primary suite features hardwood floors, pot lights, a skylight, French doors to a balcony, and a large walk-in closet. The spa-like six-piece ensuite offers a soaking tub beneath a picture window, double sinks, a rain shower with handheld, and a separate toilet room with heated floors. The second bedroom features a four-piece ensuite, skylight, double closet with built-ins, large picture window, hardwood floors, and pot lights. The third bedroom includes hardwood floors, pot lights, and a window, and shares a Jack-and-Jill five-piece bathroom with the fourth bedroom. The fourth bedroom features hardwood floors, pot lights, and a large closet. The lower level offers a spacious rec room with a built-in entertainment wall and gas fireplace, powder room, oversized storage room and laundry room with new washer and dryer (2026). 3863 Square Feet Including the basement. An in-law suite with bedroom and 3-piece ensuite provides excellent flexibility for guests or extended family. A private driveway and built-in garage provide parking for up to three vehicles. The beautiful backyard features a patio and landscaped garden. Ideally located minutes from fine dining, shops, TTC, and Leaside Station, and within the highly sought-after Bessborough & Leaside school district. More detailsListed by MCCANN REALTY GROUP LTD.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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25 Fleming Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12845798
25 Fleming Crescent Toronto M4G 2A9
$2,599,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12845798
- Bedrooms:
- 4
- Bathrooms:
- 3
Renovated 2 Storey South Leaside Detached home, with Large Main Floor Family Room Addition, main floor Powder Guest Washroom, Large Side Door Addition with large Closet and storage space. Modern Kitchen with new Quartz Counter, Backsplash, Under Counter Lighting. Opens to spacious Sunlit Family Room With 2 Skylights & Window Seat. Walk-Out from Kitchen to Serene Garden with Lily goldfish Pond, and Babbling Waterfall. Backyard widens gracefully to 33.5ft. Large Finished Lower Level Addition with Rec. Room and Office Space, High Ceilings and Walk-Up to backyard. 4th bedroom in Lower Level. Beautiful Large 3 piece basement Bathroom, with in-floor heating. Highly Sought -After, Prime Leaside Location, 5 minute walk to Bessborough Public School, Leaside High School, and Leaside Subway Station and shops on Bayview. More detailsListed by RIGHT AT HOME REALTY- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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303 33 Frederick Todd Way in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12845608
303 33 Frederick Todd Way Toronto M4G 0C9
$609,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12845608
- Bedrooms:
- 2
- Bathrooms:
- 2
Welcome To Sought-After Upper East Village, Leaside's Newest Luxury Condo Building. Gorgeous & Spacious 2 Bed 2 Bath Unit with extremely Functional layout. Enjoy Integrated Kitchen Appliances, Sleek Modern Finishes, Ensuite Laundry. Steps To Lrt Laird Station, Transit, Sunnybrook Park, Top-Rated Schools, Numerous Restaurants, Homesense, Canadian Tire, Marshalls & More! Enjoy Amazing Amenities: 24 Hr Concierge, Indoor Pool, Cardio/Weight Room, Outdoor Lounge With Fire Pit & Bbq And Private Dining. Close To Don Valley Parkway, Sunnybrook Hospital, Aga Khan Museum & Edwards Gardens. THIS Is Condo Living At It's Finest. Upper East Village is the premier choice for those who desire to have it all and enjoy the best of life in the heart of Leaside. More detailsListed by PROPERTY.CA INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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114 Glenvale Boulevard in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12843802
114 Glenvale Boulevard Toronto M4G 2V9
$1,149,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12843802
- Bedrooms:
- 2
- Bathrooms:
- 2
In the heart of Leaside, where tree-lined streets, top-ranking schools & the vibrant shops & restaurants of Bayview Ave create one of Toronto's most beloved neighbourhoods, this completely turnkey & beautifully renovated home offers effortless, modern living. Thoughtfully redesigned w/ extensive high-quality upgrades completed between 2024 & 2025, this 2-bdrm, 2-bath home has been meticulously curated so you can simply move in & enjoy. Sunlight pours through the home thanks to its coveted south exposure, illuminating the bright open-concept main flr & reconfigured expansive kitchen layout. Featuring quartz countertops seamlessly extending into matching backsplash, shaker-style cabinetry w/ soft close, premium built-ins, new appls incl. a panelled dishwasher & blanco double-basin sink, the kitchen offers exceptional storage, generous prep space & seamless access to the backyard, perfect for entertaining & everyday living. Wide-plank white oak engineered hardwood flows across the main & 2nd flr, while the fully finished bsmt provides versatile add'l living space ideal for a rec rm & home office, or guest retreat. The primary bdrm features custom floor-to-ceiling built-in closets & both bathrms have been tastefully renovated. Extensive mechanical & electrical upgrades, including a full home rewire, new panel, furnace, A/C & updated lighting, provide long-term comfort & peace of mind. Set on an extra-deep 130ft lot w/ no homes behind, the professionally landscaped backyard features a custom architect-designed deck, new fencing, cedar trees & a private outdoor oasis. A driveway extension w/ drive-safe pavers offers the convenience of 2-car parking. Spend weekends exploring nearby parks & ravine trails, visiting Trace Manes Park, Sunnybrook Park or the Leaside Library & enjoy effortless commuting w/ the Crosstown LRT, Bayview Extension & DVP nearby. All within a neighbourhood loved for its strong sense of community & seamless blend of small-town charm & urban convenience. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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5 Moorehill Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12841244
5 Moorehill Drive Toronto M4G 1A2
$2,650,000Residential Freehold- Status:
- Active Under Contract
- MLS® Num:
- C12841244
- Bedrooms:
- 4
- Bathrooms:
- 3
Situated on a spectacular, sun-filled corner lot in the heart of prestigious Bennington Heights, 5 Moorehill Drive presents a rare opportunity in one of Toronto's most exclusive and private communities.Nestled between Rosedale, Leaside, and Moore Park, Bennington Heights is a hidden enclave known for its estate-sized properties, quiet streets, and exceptional sense of community. With no through traffic, it's a place where children can still safely run to school and neighbours know one another, a true rarity in the city.Set prominently on a prime corner lot and surrounded by distinguished estate homes, this property has long been admired as a landmark residence, even highlighted and photographed as a feature home. Lovingly maintained by the same family for over 40 years, it offers a rich history and an incredible foundation for its next chapter.The existing home sits gracefully on the lot, offering a private setting with mature landscaping and abundant natural light throughout the day. A garage and generous parking provide convenience, while the expansive footprint presents endless potential to renovate, reimagine, or build new.This is a once in a generation opportunity to secure a premier corner property in the very best part of Bennington Heights, an exclusive, storybook neighbourhood where families plant roots for decades and where your vision can truly come to life. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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807 35 Brian Peck Crescent in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12835574
807 35 Brian Peck Crescent Toronto M4G 0A5
$1,095,000Residential Condo & Other- Status:
- Active Under Contract
- MLS® Num:
- C12835574
- Bedrooms:
- 3
- Bathrooms:
- 2
Scenic On Eglinton! Exceptionally spacious 1,341 sq ft corner unit. 2 bedrooms plus large separate den, 2 full baths. 2 parking spaces, 2 lockers. This contemporary suite offers a generous open concept plan with floor-to-ceiling windows and two balconies. Unit entry has hallway, with double closet, that provides privacy before leading to impressive principal areas and spectacular view. Large living and dining room is perfect for entertaining, with a walkout to 1st balcony. Kitchen features granite counter & island with breakfast bar. Oversize, bright corner den has floor-to-ceiling windows on 2 sides. Primary bedroom has modern 3-pc ensuite bath, walk-in closet and walkout to private 2nd balcony! Split bedroom plan features 2nd bedroom with a walk-in closet and a walkout to the main balcony. 4-pc bath and laundry. Enjoy an unobstructed expansive view of natural greenery and nearby ravine. Great amenities include 24-hour concierge, gym, indoor pool, party/meeting room and more! Terrific Leaside location, easy access to Hwy 404 & 401, new Eglinton LRT. Wilket Creek & Sunnybrook Parks, Sunnybrook Hospital, short drive to Shops At Don Mills. Don't miss this rare, fabulous suite. 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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165 Leacrest Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12833832
165 Leacrest Road Toronto M4G 1E7
$4,990,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12833832
- Bedrooms:
- 5
- Bathrooms:
- 6
Newly built modern residence in the heart of South Leaside offering nearly 6,500 sq.ft. of living space! Exceptional designer-curated finishes and smart home technology throughout. Designed for the modern family and built to impress, this magazine-worthy residence perfectly blends luxury, functionality, and versatility. Oversized principal rooms, two private home offices, and a full legal in-law suite with income potential make it ideal for multigenerational living or a flexible live-work lifestyle.Showcasing engineered white oak floors, soaring ceilings, and expansive windows with motorized blinds, every detail reflects thoughtful design and quality craftsmanship. The custom kitchen is a true centerpiece - featuring a panelled fridge, trash compactor, waterfall island with hidden storage, and full-height cabinetry - flowing seamlessly into the family room with a marble gas fireplace and walkout to the backyard. Step lighting, integrated speakers, and sleek modern finishes complete the main level's sophisticated aesthetic.Upstairs, four oversized bedrooms include a magazine-worthy primary suite with a slatted wood feature wall access to His & Hers WICs, cove-lit ceiling, fireplace in stone surround, fully equipped bar, walkout to a private balcony (hot tub-ready), and a spa-inspired ensuite with steam shower, freestanding tub, heated floors, and double vanities. Secondary bedrooms are equally impressive, and a dedicated laundry room with dual washer/dryers enhances everyday ease. Upstairs office may be converted to a 5th bedroom.The lower level extends the living experience with a gym, sauna, recreation lounge, and wet bar equipped with a dishwasher and bar fridge - plus a soundproofed legal in-law suite with its own entrance, kitchen, 3-piece bath & laundry.Located in the coveted Bessborough/Rolph school district, this home delivers a rare combination of sophistication, functionality, and future income potential in one of Toronto's most sought-after neighbourhoods. More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
Data was last updated March 12, 2026 at 06:15 AM (UTC)
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