Homes For Sale In Leaside + Bennington Heights
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252 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12603502
252 Sutherland Drive Toronto M4G 1J3 
$3,150,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12603502
- Bedrooms:
- 5
- Bathrooms:
- 4
This sophisticated and luxurious custom built 4+1 bedroom residence in coveted South Leaside has it all! Designed by renowned architect Lorne Rose, this meticulous home has grand principal rooms, a renovated gourmet kitchen with eat-in dining, adjoining family room with fireplace and walk-out to stunning rear gardens. The spacious second storey with custom skylight has 4 bedrooms including a sumptuous and private primary retreat with walk-in closet and 5-piece ensuite. The expansive lower level features a large recreation room plus a children's play area, 5th bedroom, 3-piece bath, laundry room, cedar closet (potential for wine cellar) and storage. Located on a quiet family friendly street in prime South Leaside with curb appeal galore, it has an all brick exterior with custom Indiana limestone detailing and custom designed elevated landscaping. The superb layout offers 3,300+ square feet of functional family space. Front drive parking plus custom built 1 1/2 car garage accessed via laneway provides ample parking. (Please note that built-in desk in living room can remain or be removed if preferred *refer to photos of prior living room set-up). Pristine landscaping with in ground irrigation system and outdoor lighting. "Other" room is a cedar closet with potential for wine cellar. More detailsListed by CHESTNUT PARK REAL ESTATE LIMITED- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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349 Laird Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12597714
349 Laird Drive Toronto M4G 3Y1
$1,655,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12597714
- Bedrooms:
- 4
- Bathrooms:
- 3
Incredible location in the quiet residential section of Laird. This bright, spacious, and sun-filled two-storey home features a tasteful addition and is situated in the highly desirableNorth Leaside area. Offering 3+1 bedrooms and 3 bathrooms, the primary bedroom includes a4-piece ensuite and walk-in closet. Additional highlights include a gas burning fireplace, stainless steel appliances, a private backyard, gas furnace, and central A/C. A private driveway provides parking for up to 3 cars. The property is also conveniently close to Northlea Elementary & Middle School, shopping centres, parks, and the TTC. More detailsListed by GATE REAL ESTATE INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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775 Millwood Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12595610
775 Millwood Road Toronto M4G 1V7
$1,699,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12595610
- Bedrooms:
- 4
- Bathrooms:
- 3
Welcome to 775 Millwood Road, Toronto (South Leaside) steps from Bayview Ave restaurants and shops. Discover this charming and versatile legal duplex, offering the flexibility to enjoy as a single-family home or as two separate units. The upper level features two spacious bedrooms plus a family room, a beautifully renovated kitchen with a dining room, and a 4-piece bathroom. The main floor boasts two bedrooms, including a primary suite with a walkout to a large private deck. The open-concept renovated kitchen overlooks the dining area and flows into the inviting living family room. Step outside to your own backyard oasis, complete with a hot tub and separate lap pool/endless pool perfect for relaxing or entertaining. Additional highlights include a single-car garage. Two staircases and separate entrance to lower level. Short walk to all amenities including local library, parks, TTC, Ice Arena and great schools plus much more. 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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9 True Davidson Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12591016
9 True Davidson Drive Toronto M4W 3X2 OPEN HOUSE: Dec 07, 202502:00 PM - 04:00 PM ESTOpen House on Sunday, December 7, 2025 2:00PM - 4:00PM
$2,948,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12591016
- Bedrooms:
- 3
- Bathrooms:
- 5
Welcome to 9 True Davidson, a grand home nestled at the end of cul de sac in the coveted neighbourhood of Governor's Bridge, a peaceful tree-lined pocket perfect for families seeking tranquility and privacy with an easy 15-min drive to downtown and uptown Toronto. Charm and elegance exudes from the house as you are greeted by soaring ceilings, a marble-lined foyer and mahogany flooring throughout. The home features three bedrooms including a double-sized primary bedroom with walk-in closet and ensuite bathroom, multiple entertaining spaces with working wood and gas fireplaces, custom kitchen, finished basement, patios you can walk out to from the living room and basement, and an attached garage with two-car parking with private drive. Discover your new home in this gorgeous turnkey house in the neighbourhood everyone wants to be. More detailsListed by RE/MAX HALLMARK BATORI GROUP INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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316 211 Randolph Road in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12582014
316 211 Randolph Road Toronto M4G 4H1
$625,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12582014
- Bedrooms:
- 2
- Bathrooms:
- 2
Light-filled 2 bedroom, 2 baths Family Condo in Prime Leaside. Renovated and Well-Kept East-Facing Unit with Custom Built-in Wall-Shelving Systems, Hardwood Floors and Pot Lights in All the Rooms. Close to Great Schools, Biking Trails, Shopping, Steps from the New LRT; a Pet-Friendly Building. Status Certificate Available. Fridge, Stove, D/W, Washer, Dryer, a Wall-Mounted Television, California Shutters. The Hot Water Tank is a Rental. *For Additional Property Details Click The Brochure Icon Below* More detailsListed by ICI SOURCE REAL ASSET SERVICES INC.- 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®# C12580962
606 25 Malcolm Road Toronto M4G 0C1
$799,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12580962
- Bedrooms:
- 2
- Bathrooms:
- 2
Chic 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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35 Fleming Crescent in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12580830
35 Fleming Crescent Toronto M4G 2A9
$3,288,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12580830
- Bedrooms:
- 5
- Bathrooms:
- 5
A Striking Blend of Classic and Contemporary on One of Leaside's Most Prominent Streets. Perfectly positioned on sought-after Fleming Cres, this stunning red-brick Transitional/Neo-Georgian inspired residence offers approximately 3,695 sq. ft. of luxury living space. Blending timeless elegance with modern design, it delivers the best of both worlds in one of Toronto's most coveted neighbourhoods. Inside, wood floors flow throughout, while a dramatic skylight staircase bathes the interior in natural light. The main level is anchored by a chef's kitchen - a true culinary dream - featuring a Thermador 6-burner gas range with grill, Thermador fridge & built-in oven, a large stone waterfall island, and butler's pantry with a 2nd dishwasher. The kitchen opens seamlessly to a sunlit family room, where custom built-ins and a sleek linear gas fireplace create a warm and sophisticated ambiance. Sliding doors extend the living space to a private backyard oasis. Impressive 10' ceilings enhance the main floor w/coffered ceilings in the living/dining adding architectural elegance, perfect for hosting memorable gatherings. Upper level boasts four generous bedrooms, including a primary retreat designed for luxury living. The spa-inspired ensuite is finished in Italian marble and offers heated floors, a soaker tub, glass shower with bench and body jets, plus a custom walk-in closet with additional laundry hookup for convenience. Three additional bedrooms and two full baths complete this level. The fully finished lower level offers radiant heated floors, a spacious rec room, laundry, 4-piece bath, and an additional 5th bedroom or guest/nanny room, providing versatility for guests or extended family. The private drive and built-in garage w/direct home access provide everyday convenience and additional storage, perfectly complementing the thoughtful design of this family home. Steps to top-rated schools, parks, shops, TTC, library, Sunnybrook Hospital. Walk Score 97! 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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31 Governors Road in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12572668
31 Governors Road Toronto M4W 2E9
$4,450,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12572668
- Bedrooms:
- 3
- Bathrooms:
- 4
31 Governors Road is a European-inspired contemporary villa designed by Francesco and Aldo Piccaluga, the award-winning brothers whose work helped shape a distinct era of Toronto architecture. Conceived of as a villa in the city, the home is a study in contrasts: privacy without loss of light, openness alongside clearly defined rooms, and natural materials set against brick and concrete. Completed in the early 1990s and cared for by only two families since, the home balances architectural pedigree & high design with remarkable adaptability. The current owner has infused elements of play and light, yet the design could easily accommodate traditional, contemporary, or eclectic sensibilities. At its core, a dramatic marble staircase anchors the flowing layout. The custom Valcucine kitchen is finished with natural stone and high-end appliances, opening seamlessly to a 600-square-foot entertaining terrace. The expansive living room, warmed by a wood-burning fireplace, is softly lit through glass block throwing light against Venetian plaster walls, creating intimacy and comfort. Upstairs, the serene primary suite features a six-piece spa-like ensuite and a walk-in closet with striking boudoir. The lower level continues the theme of retreat and versatility: a saltwater indoor pool and exercise area invite restoration, while an oversized recreation room with kitchenette can readily adapt to serve as an in-law or teen suite. Ingeniously designed moats flank the foundation, allowing full-sized windows that fill the lower level with light and fresh air. Outside, Mediterranean hues of burnt clay and soft white highlight the bold geometric volumes so emblematic of the Piccaluga Brothers work. The result is both iconic and timeless. 31 Governors Road is an architectural triumph and an enduring postmodern masterpiece in the heart of Toronto that is not to be missed. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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431 Heath Street E in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12566866
431 Heath Street E Toronto M4G 1B6
$6,398,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12566866
- Bedrooms:
- 5
- Bathrooms:
- 6
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. More detailsListed by RE/MAX REALTRON REALTY INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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317 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C12558266
317 Sutherland Drive Toronto M4G 1J6
$3,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12558266
- Bedrooms:
- 5
- Bathrooms:
- 5
Impeccably designed and custom-built Leaside home. This stunning 4+1 bedroom, 5-bathroom home offers nearly 3,700 sq.ft. of meticulously crafted living space in the heart of Leaside. Designed with timeless elegance and modern functionality, the home features soaring ceilings, refined millwork, premium hardwood floors, and a spacious open-concept layout ideal for both everyday living and sophisticated entertaining. The chef's kitchen showcases high-end appliances, custom cabinetry, an oversized island, and seamless flow to a sun-filled family room with walkout to a beautifully landscaped backyard. The upper level offers generous bedrooms including a luxurious primary retreat with walk-in closet and spa-inspired ensuite. The fully finished lower level includes a large recreation room, additional bedroom, full bathroom, and ample storage. With exceptional attention to detail and finishes that rival a model home, this property delivers turnkey luxury in one of Toronto's most sought-after neighbourhoods, steps to top-rated schools, parks, shopping, and transit. Intangibles that you wouldn't know unless you lived here: the neighbours are incredible, ultra quiet, the dead end laneway means no through traffic, gives an additional 600sq.ft. of backyard space ideal for kids play area. Permitted laneway usage, you can build an additional 1600sq.ft. in the backyard, or scale it down to a 450sq.ft office/flex space, plans have been approved and are transferrable. More detailsListed by YOUNG REALTY INC.- Chantel Crisp
- Royal LePage Signature Realty, Brokerage
- 647-967-9677
- info@chantelcrispteam.com
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209 356 Mcrae Drive in Toronto: Leaside Condo Apartment for sale (Toronto C11) : MLS®# C12556814
209 356 Mcrae Drive Toronto M4G 4G4
$569,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12556814
- Bedrooms:
- 2
- Bathrooms:
- 1
Welcome to Suite 209 at The Randolph in Leaside Nestled among the treetops, this beautifully updated and exceptionally spacious one-bedroom and den offers over 850 square feet of well-planned living. Perfect for first time buyers or those looking to downsize without compromise, this suite features expansive living and dining areas, a bright sunroom-style den, and thoughtful storage throughout. The updated kitchen is both functional and inviting, complete with stainless steel appliances, and a convenient breakfast bar-ideal for casual dining or morning coffee. The large living and dining rooms easily accommodate full-sized furnishings, while the sunlit den offers the perfect spot for reading, working, or relaxing. The generous primary bedroom includes customized his-and-hers California Closet built-ins and semi-ensuite access to a well-appointed four-piece bath. A full-sized laundry room with additional storage adds to the suite's exceptional practicality. The Randolph is a quiet, boutique-style low-rise with a strong sense of community and long-term residents. Amenities include a party room, exercise room, residents' lounge and a beautiful private terrace with barbecue and lounge area. Located just steps from Leaside village and minutes from Trace Manes Park, Leaside Library, and the Eglinton Crosstown, this location can't be beat. 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®# C12555360
807 35 Brian Peck Crescent Toronto M4G 0A5
$1,095,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12555360
- 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
Data was last updated December 6, 2025 at 10:15 PM (UTC)
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