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Leaside, Toronto, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Leaside. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Leaside

Last Updated: November 08, 2026

50 Photos

32 Evergreen Gardens, Toronto, ON , MLS #C14094926 , Image - 1

32 Evergreen Gardens Leaside, Toronto, ON MLS® C14094926

Residential Freehold (Att/Row/Townhouse)

$2798000.0

3 +1 Beds
4 Baths
3000-3500 sq-ft

NEW PRICE! Exceptional value in exclusive Bennington Heights. Part of an intimate luxury collection of just five bespoke residences, Three are sold, o

50 Photos

354 Bessborough Drive, Toronto, ON , MLS #C13660624 , Image - 1

354 Bessborough Drive Leaside, Toronto, ON MLS® C13660624

Residential Freehold (Detached)

$3299999.0

4 +2 Beds
5 Baths
2500-3000 sq-ft

Welcome home to this beautifully renovated 2-storey residence in the heart of Leaside - one of Toronto's most sought-after family neighborhoods. This

41 Photos

10 Red Oaks Crescent, Toronto, ON , MLS #C14129218 , Image - 1

10 Red Oaks Crescent Leaside, Toronto, ON MLS® C14129218

Residential Freehold (Detached)

$3250000.0

3 +1 Beds
3 Baths
1500-2000 sq-ft

Set on a quiet, tree-lined street in coveted Bennington Heights, this beautifully renovated bungalow offers a rare combination of architectural warmth

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

28 Photos

112 Southvale Drive, Toronto, ON , MLS #C14124338 , Image - 1

112 Southvale Drive Leaside, Toronto, ON MLS® C14124338

Residential Freehold (Detached)

$2175000.0

4 +1 Beds
3 Baths
1500-2000 sq-ft

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

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

Pre-Construction

Lily at Crosstown

844 Don Mills Road, North York, Toronto

From $573,990 - $1,358,990

Project Info

2 Buildings
220 Units
Condos

Property Mix

Studio(2)
1 Bed(95)
2 Bed(79)
3 Bed(44)

Developer:Aspen Ridge Homes

11 Photos

7 Lumley Avenue, Toronto, ON , MLS #C14147496 , Image - 1

7 Lumley Avenue Leaside, Toronto, ON MLS® C14147496

Residential Freehold (Detached)

$6595000.0

4 +1 Beds
7 Baths
3500-5000 sq-ft

A stunning, brand new modern home in Bennington Heights, thoughtfully designed with a focus on light, proportion, and practical family living. Set on

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

45 Photos

15 Moorehill Drive, Toronto, ON , MLS #C14010858 , Image - 1

15 Moorehill Drive Leaside, Toronto, ON MLS® C14010858

Residential Freehold (Detached)

$3900000.0

5 +1 Beds
4 Baths
3000-3500 sq-ft

An exceptional family residence set on a impressive 76-foot lot in prestigious Bennington Heights, this beautifully appointed home offers 4,772 sq ft

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

50 Photos

122 Brentcliffe Road, Toronto, ON , MLS #C14133866 , Image - 1

122 Brentcliffe Road Leaside, Toronto, ON MLS® C14133866

Residential Freehold (Detached)

$2299000.0

3 +2 Beds
4 Baths
2000-2500 sq-ft

Welcome to 122 Brentcliffe Road, a bright and inviting family home in the highly sought-after community of Leaside. Warm, welcoming and thoughtfully l

Open House : Sun Nov 08, 02:00 PM to 04:00 PM

35 Photos

48 Sharron Drive, Toronto, ON , MLS #C14029936 , Image - 1

48 Sharron Drive Leaside, Toronto, ON MLS® C14029936

Residential Freehold (Detached)

$3449000.0

4 +1 Beds
4 Baths
2000-2500 sq-ft

Stunning Custom-Built Residence In The Highly Sought-After Bessborough School District! Steps To The Vibrant Shops, Restaurants And Cafés Along Bayvie

Pre-Construction

The Clove Condos

2 East Mall Cres, Toronto

From $440,990

Project Info

1 Building
606 Units
Condos

Property Mix

Studio(32)
1 Bed(379)
2 Bed(127)
3 Bed(68)

Developer:Mattamy Homes, QuadReal Property Group

1 Photos

127 Glenvale Boulevard Leaside, Toronto, ON MLS® C14028884

Residential Freehold (Semi-Detached )

$2088000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to a home ( Legal Duplex) where thoughtful design meets elevated living. A beautiful transformed three-bedroom semi that blends luxury, functi

50 Photos

10 Field Avenue, Toronto, ON , MLS #C14106058 , Image - 1

10 Field Avenue Leaside, Toronto, ON MLS® C14106058

Residential Freehold (Detached)

$4499000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

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 renov

39 Photos

34 Glenbrae Avenue, Toronto, ON , MLS #C14115812 , Image - 1

34 Glenbrae Avenue Leaside, Toronto, ON MLS® C14115812

Residential Freehold (Detached)

$3199000.0

4 +1 Beds
4 Baths
2000-2500 sq-ft

A spectacular one-of-a-kind North Leaside home that makes you dream of long summer days spent poolside, dinner underway in the outdoor kitchen, the ga

50 Photos

442 Heath Street E, Toronto, ON , MLS #C14127394 , Image - 1

442 Heath Street E Leaside, Toronto, ON MLS® C14127394

Residential Freehold (Detached)

$9495000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

Welcome to 442 Heath Street East, an architecturally distinctive contemporary residence offering more than 6,000 square feet across three levels in co

38 Photos

431 Heath Street E, Toronto, ON , MLS #C13778884 , Image - 1

431 Heath Street E Leaside, Toronto, ON MLS® C13778884

Residential Freehold (Detached)

$5949000.0

4 +1 Beds
6 Baths
3500-5000 sq-ft

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 rede

49 Photos

164 Glenvale Boulevard, Toronto, ON , MLS #C14091094 , Image - 1

164 Glenvale Boulevard Leaside, Toronto, ON MLS® C14091094

Residential Freehold (Detached)

$2150000.0

3 Beds
3 Baths
1500-2000 sq-ft

Enjoy the Best of Leaside Living. Experience the space, comfort and lifestyle that make Leaside such a sought-after Toronto neighbourhood. Enjoy open,

49 Photos

35 Bessborough Drive, Toronto, ON , MLS #C14011372 , Image - 1

35 Bessborough Drive Leaside, Toronto, ON MLS® C14011372

Residential Freehold (Detached)

$3650000.0

5 Beds
5 Baths
3000-3500 sq-ft

A rare offering on Bessborough in the heart of Leaside: a beautifully renovated 3-bedroom 3-bathroom home home paired with a brand-new, exceptionally

33 Photos

551 Broadway Avenue, Toronto, ON , MLS #C14089238 , Image - 1

551 Broadway Avenue Leaside, Toronto, ON MLS® C14089238

Residential Freehold (Detached)

$3899000.0

3 Beds
5 Baths
2500-3000 sq-ft

Exceptional Custom-Built Luxury Home In Prestigious North Leaside! Completed In 2024, This Stunning Approx. 3,000 Sq. Ft. Detached Residence Showcases

47 Photos

553 Broadway Avenue, Toronto, ON , MLS #C13753904 , Image - 1

553 Broadway Avenue Leaside, Toronto, ON MLS® C13753904

Residential Freehold (Detached)

$3475000.0

Price drop by 2.1%

4 +1 Beds
5 Baths
2000-2500 sq-ft

This Leaside jewel has serious attention to detail everywhere you look. Classic finishes with design elements well integrated throughout the entire ho

50 Photos

319 Rumsey Road, Toronto, ON , MLS #C13831502 , Image - 1

319 Rumsey Road Leaside, Toronto, ON MLS® C13831502

Residential Freehold (Detached)

$3589000.0

4 Beds
4 Baths
2500-3000 sq-ft

Welcome to 319 Rumsey Rd, a beautifully renovated 2,600 sq. ft. home in the highly sought-after Leaside community! This exceptional residence features

38 Photos

4 Douglas Crescent, Toronto, ON , MLS #C13854620 , Image - 1

4 Douglas Crescent Leaside, Toronto, ON MLS® C13854620

Residential Freehold (Detached)

$4999000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

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 bed

50 Photos

38 Killdeer Crescent, Toronto, ON , MLS #C13830842 , Image - 1

38 Killdeer Crescent Leaside, Toronto, ON MLS® C13830842

Residential Freehold (Detached)

$3895000.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

Tucked away on one of North Leaside's most coveted streets, this exceptional ravine property offers a rare sense of space, privacy, and possibility. W

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40 Divadale Drive, Toronto, ON , MLS #C13754186 , Image - 1

40 Divadale Drive Leaside, Toronto, ON MLS® C13754186

Residential Freehold (Detached)

$3999999.0

4 +1 Beds
5 Baths
2000-2500 sq-ft

Welcome to an exceptional custom residence in the heart of coveted North Leaside. Impeccably designed with refined craftsmanship, sophisticated finish

Shortlisted Properties

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Leaside, Toronto, ON Luxury Homes

Lily at Crosstown

The Clove Condos

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