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House for Sale near Highland Avenue and Glen Road, C09

Showing results 1 - 30 of 30

Explore over 30 houses for sale near Highland Avenue and Glen Road with Square Yards Canada. Our listings include numerous property types, such as freehold homes, condos, and commercial properties. You can filter through listings by price range to find options that match your budget and refine your search based on the number of bedrooms, bathrooms, and surface areas. Choose from properties with specific amenities, ensuring you find affordable and luxury houses for sale near Highland Avenue and Glen Road. Browse through detailed listings with HD images and comprehensive guides. Square Yards Canada makes it easy to find houses for sale near Highland Avenue and Glen Road that are perfect for you.

Last Updated: November 12, 2026

47 Photos

63 Astley Avenue, Toronto, ON , MLS #C14145416 , Image - 1

0.99 km from Highland Avenue and Glen Road

63 Astley Avenue Rosedale-Moore Park, Toronto, ON MLS® C14145416

Residential Freehold (Detached)

$2349000.0

3 +1 Beds
2 Baths
1100-1500 sq-ft

A Ravine Retreat on a Quiet Rosedale Street! This beautifully renovated modern 3+1 bedroom, 2 bathroom detachedgem sits on a quiet North Rosedale stre

Open House : Sat Nov 14, 02:00 PM to 04:00 PM

41 Photos

126A Glen Road, Toronto, ON , MLS #C14164644 , Image - 1

0.11 km from Highland Avenue and Glen Road

126A Glen Road Rosedale-Moore Park, Toronto, ON MLS® C14164644

Residential Freehold (Detached)

$5995000.0

4 +3 Beds
7 Baths
3500-5000 sq-ft

A rare and distinguished offering on prestigious Binscarth Road at Glen Road, in the heart of North Rosedale. This stately three-storey detached resid

50 Photos

43 Whitehall Road, Toronto, ON , MLS #C14171990 , Image - 1

0.65 km from Highland Avenue and Glen Road

43 Whitehall Road Rosedale-Moore Park, Toronto, ON MLS® C14171990

Residential Freehold (Detached)

$3850000.0

4 Beds
4 Baths
3000-3500 sq-ft

Tucked along one of Rosedale's most coveted streets, 43 Whitehall Road is a rare offering: an impeccably finished family home with all the pedigree of

28 Photos

45 Mathersfield Drive, Toronto, ON , MLS #C13791164 , Image - 1

1.09 km from Highland Avenue and Glen Road

45 Mathersfield Drive Rosedale-Moore Park, Toronto, ON MLS® C13791164

Residential Freehold (Detached)

$4599000.0

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

Luxury meets location is South Rosedale! Nestled in one of Torontos most prestigious neighbourhoods, this South Rosedale gem is part of a rare, exclus

Pre-Construction

1515 Pickering Parkway

1497-1525 Pickering Parkway, Pickering

From $399,990 - $706,990

Project Info

1 Building
571 Units
Condos

Property Mix

Studio(36)
1 Bed(451)
2 Bed(80)
3 Bed(2)

Developer:Sevoy Developments

35 Photos

20 Edgewood Crescent, Toronto, ON , MLS #C13769036 , Image - 1

0.75 km from Highland Avenue and Glen Road

20 Edgewood Crescent Rosedale-Moore Park, Toronto, ON MLS® C13769036

Residential Freehold (Detached)

$3250000.0

5 Beds
4 Baths
2500-3000 sq-ft

Welcome to 20 Edgewood Crescent - located in coveted North Rosedale, this home checks every box! Set on a coveted, quiet dead-end cul-de-sac, this gra

Open House : Sun Nov 15, 02:00 PM to 04:00 PM

40 Photos

155 South Drive, Toronto, ON , MLS #C13816450 , Image - 1

0.46 km from Highland Avenue and Glen Road

155 South Drive Rosedale-Moore Park, Toronto, ON MLS® C13816450

Residential Freehold (Detached)

$7895000.0

4 +1 Beds
7 Baths
5000 + sq-ft

155 South Drive - This is the stunning South Rosedale Home you've been looking for! Commandingly positioned on one of the neighbourhood's most coveted

Open House : Sun Nov 15, 02:00 PM to 04:00 PM

35 Photos

50 Nanton Avenue, Toronto, ON , MLS #C14095964 , Image - 1

0.53 km from Highland Avenue and Glen Road

50 Nanton Avenue Rosedale-Moore Park, Toronto, ON MLS® C14095964

Residential Freehold (Detached)

$5295000.0

6 Beds
4 Baths
3000-3500 sq-ft

A magnificent Rosedale Grand Dame! Set majestically on an exceptional 50' x 150' lot in coveted South Rosedale, this distinguished red-brick residence

Open House : Sun Nov 15, 02:00 PM to 04:00 PM

39 Photos

32 Sherbourne Street N, Toronto, ON , MLS #C14138762 , Image - 1

0.7 km from Highland Avenue and Glen Road

32 Sherbourne Street N Rosedale-Moore Park, Toronto, ON MLS® C14138762

Residential Freehold (Detached)

$7995000.0

6 Beds
5 Baths
5000 + sq-ft

In the very heart of prestigious South Rosedale, on 1/3rd of an acre of deep tableland, stands a 1910 residence of enduring grandeur. A remarkable off

Pre-Construction

Arbor West

10024 Mississauga Road, Brampton

From $559,990

Project Info

88 Buildings
204 Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Caivan

50 Photos

71 Welland Avenue, Toronto, ON , MLS #C14140922 , Image - 1

1.2 km from Highland Avenue and Glen Road

71 Welland Avenue Rosedale-Moore Park, Toronto, ON MLS® C14140922

Residential Freehold (Detached)

$5150000.0

3 Beds
3 Baths
2500-3000 sq-ft

Exceptional, newly landscaped & meticulously renovated throughout, one-of-a-kind gem in Moore Park/Rosedale! Remarkable attention to top quality finis

Open House : Sun Nov 15, 02:00 PM to 04:00 PM

37 Photos

575 Bloor Street E, Toronto, ON , MLS #C14107150 , Image - 1

1.03 km from Highland Avenue and Glen Road

Unit-3405, 575 Bloor Street E North St. James Town, Toronto, ON MLS® C14107150

Residential Condo & Other (Condo Apartment)

$549000.0

1 +1 Beds
1 Baths
500-599 sq-ft

Welcome To This Luxury Tridel Built Via Bloor, 1-Bed Plus Den Condo Unit, Where Modern Elegance Meets Urban Convenience In The Heart Of Downtown Toron

31 Photos

360 Bloor Street E, Toronto, ON , MLS #C14168572 , Image - 1

1.01 km from Highland Avenue and Glen Road

Unit-1007, 360 Bloor Street E Rosedale-Moore Park, Toronto, ON MLS® C14168572

Residential Condo & Other (Condo Apartment)

$799000.0

2 Beds
2 Baths
1400-1599 sq-ft

An Iconic & Timeless Suite, This Expansive 1510 Square Foot, Two-Bedroom, Two-Bathroom Residence Situated Just Steps From Rosedale & Yorkville Provide

30 Photos

21 Dale Avenue, Toronto, ON , MLS #C14168466 , Image - 1

0.83 km from Highland Avenue and Glen Road

Unit-945, 21 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C14168466

Residential Condo & Other (Co-op Apartment)

$785000.0

2 Beds
2 Baths
1200-1399 sq-ft

This spacious 1222-sq-ft single-level suite features two well-sized bedrooms and one and a half updated bathrooms (2021). Tons of storage throughout.

Pre-Construction

Corktown Plaza

221 John Street South, Hamilton

From $329,900

Project Info

2 Buildings
786 Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Slate Asset Management

47 Photos

42 Crescent Road, Toronto, ON , MLS #C13781462 , Image - 1

1.15 km from Highland Avenue and Glen Road

42 Crescent Road Rosedale-Moore Park, Toronto, ON MLS® C13781462

Residential Freehold (Detached)

$4695000.0

Price drop by 5.2%

6 Beds
4 Baths
3500-5000 sq-ft

A grand three storey century home in prime South Rosedale, 42 Crescent Road is an impressive Dutch Colonial Revival residence set gracefully behind ma

50 Photos

300 Bloor Street E, Toronto, ON , MLS #C14167556 , Image - 1

1.12 km from Highland Avenue and Glen Road

Unit-3010, 300 Bloor Street E Rosedale-Moore Park, Toronto, ON MLS® C14167556

Residential Condo & Other (Condo Apartment)

$938888.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to 300 Bloor: A Manhattan feeling in the heart of Toronto! Perched high above the green canopy of the Rosedale Valley Ravine, like an eagle's

34 Photos

291 St Clair Avenue, Toronto, ON , MLS #C14150752 , Image - 1

1.25 km from Highland Avenue and Glen Road

291 St Clair Avenue Rosedale-Moore Park, Toronto, ON MLS® C14150752

Residential Freehold (Detached)

$1599000.0

3 +2 Beds
3 Baths
1100-1500 sq-ft

Welcome to 291 St Clair Avenue East, a detached 2-storey home in Moore Park situated on a deep 22 x 143-foot lot with an interlocking front yard drive

50 Photos

17A Avondale Road, Toronto, ON , MLS #C14145102 , Image - 1

1.02 km from Highland Avenue and Glen Road

17A Avondale Road Rosedale-Moore Park, Toronto, ON MLS® C14145102

Residential Freehold (Detached)

$6999000.0

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

An exceptional DETACHED French Neoclassical residence on one of South Rosedale's most prestigious streets, this architecturally distinctive home offer

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

32 Photos

278 Bloor Street E, Toronto, ON , MLS #C14165054 , Image - 1

1.12 km from Highland Avenue and Glen Road

Unit-2205, 278 Bloor Street E Rosedale-Moore Park, Toronto, ON MLS® C14165054

Residential Condo & Other (Condo Apartment)

$1699000.0

3 +1 Beds
2 Baths
1800-1999 sq-ft

Welcome to Rosedale Glen, an established luxury condominium residence in the heart of the city. This beautifully appointed, light-filled sub-penthouse

40 Photos

409 Bloor Street E, Toronto, ON , MLS #C14121898 , Image - 1

1.01 km from Highland Avenue and Glen Road

Unit-PH1, 409 Bloor Street E Rosedale-Moore Park, Toronto, ON MLS® C14121898

Residential Condo & Other (Condo Apartment)

$2995000.0

4 Beds
5 Baths
4750-4999 sq-ft

A ONE-OF-A-KIND TORONTO PENTHOUSE, NEWLY RENOVATED. An extraordinary offering, this spectacular two-level, 5,000-square-foot penthouse encompasses the

38 Photos

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

1.2 km from Highland Avenue and Glen Road

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

Open House : Sun Nov 15, 02:00 PM to 04:00 PM

26 Photos

94 Roxborough Drive, Toronto, ON , MLS #C14027922 , Image - 1

0.35 km from Highland Avenue and Glen Road

94 Roxborough Drive Rosedale-Moore Park, Toronto, ON MLS® C14027922

Residential Freehold (Detached)

$4650000.0

2 +1 Beds
3 Baths
2000-2500 sq-ft

A rare blend of sophistication, privacy & serenity at 94 Roxborough Drive, an extraordinary North Rosedale residence. Nestled beneath a lush canopy of

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

23 Photos

75 Crescent Road, Toronto, ON , MLS #C14161840 , Image - 1

0.95 km from Highland Avenue and Glen Road

Unit-301, 75 Crescent Road Rosedale-Moore Park, Toronto, ON MLS® C14161840

Residential Condo & Other (Condo Apartment)

$1390000.0

2 Beds
2 Baths
1200-1399 sq-ft

Discover your perfect Rosedale condo unit in the beautifully restored Castlemere, nestled among picturesque, tree-lined streets. This sun-filled, reno

50 Photos

29 Standish Avenue, Toronto, ON , MLS #C14130340 , Image - 1

0.85 km from Highland Avenue and Glen Road

29 Standish Avenue Rosedale-Moore Park, Toronto, ON MLS® C14130340

Residential Freehold (Detached)

$2645000.0

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

A Private Retreat With Just Over 3300 Square Feet Of Functional Living Space On 3 Levels. An Extraordinary Setting. Tucked Away On One Of North Roseda

23 Photos

266 Douglas Drive, Toronto, ON , MLS #C13781026 , Image - 1

0.64 km from Highland Avenue and Glen Road

266 Douglas Drive Rosedale-Moore Park, Toronto, ON MLS® C13781026

Residential Freehold (Detached)

$10995000.0

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

One of North Rosedale's most admired and coveted estate residences, originally built in 1921, has undergone a complete transformation and expansion un

26 Photos

575 Bloor Street E, Toronto, ON , MLS #C14087836 , Image - 1

1.03 km from Highland Avenue and Glen Road

Unit-3203, 575 Bloor Street E North St. James Town, Toronto, ON MLS® C14087836

Residential Condo & Other (Condo Apartment)

$798000.0

2 Beds
2 Baths
900-999 sq-ft

Tridel Built - 2 Bedrooms With 2 Bathrooms Corner Unit, Unobstructed North East View, Very Convenient Downtown Location, Close To Ttc, Subway And High

Pre-Construction

The Laurels

6100 Regional Road 25, Milton

From $506,990 - $795,990

Project Info

7 Buildings
1768 Units
Condos

Property Mix

1 Bed(1425)
2 Bed(343)

Developer:Mattamy Homes

35 Photos

70 Summerhill Gardens, Toronto, ON , MLS #C14157484 , Image - 1

1.02 km from Highland Avenue and Glen Road

70 Summerhill Gardens Rosedale-Moore Park, Toronto, ON MLS® C14157484

Residential Freehold (Att/Row/Townhouse)

$1849000.0

2 Beds
2 Baths
1100-1500 sq-ft

Set on a tree-lined Summerhill street and backing onto a lush ravine, this beautifully finished two-bedroom home offers the ease of condo living with

33 Photos

395 Bloor Street E, Toronto, ON , MLS #C13566896 , Image - 1

1.02 km from Highland Avenue and Glen Road

Unit-4203, 395 Bloor Street E North St. James Town, Toronto, ON MLS® C13566896

Residential Condo & Other (Condo Apartment)

$659999.0

Price drop by 8.3%

2 Beds
2 Baths
800-899 sq-ft

Experience luxury urban living at The Rosedale on Bloor in this bright and spacious 2-bedroom, 2-bathroom suite featuring a highly desirable open-conc

25 Photos

31 Rosedale Road, Toronto, ON , MLS #C14155168 , Image - 1

0.95 km from Highland Avenue and Glen Road

Unit-101, 31 Rosedale Road Rosedale-Moore Park, Toronto, ON MLS® C14155168

Residential Condo & Other (Co-op Apartment)

$698800.0

2 Beds
1 Baths
1000-1199 sq-ft

Charming condo living in prestigious Rosedale! Discover the charm and elegance of the Dale Avon Condos, nestled on a beautiful, mature tree-lined stre

40 Photos

21 Dale Avenue, Toronto, ON , MLS #C14152846 , Image - 1

0.83 km from Highland Avenue and Glen Road

Unit-722, 21 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C14152846

Residential Condo & Other (Co-op Apartment)

$769900.0

2 Beds
1 Baths
1000-1199 sq-ft

An iconic development in the heart of South Rosedale, sitting on 5 acres backing onto the Rosedale ravine with manicured gardens, trails & paths, incr

Pre-Construction

The Rebecca Condos

71 Rebecca Street, Hamilton

From $528,990 - $709,990

Project Info

1 Building
477 Units
Condos

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes, Melrose Investments

19 Photos

18 Doncrest Road, Toronto, ON , MLS #E13767584 , Image - 1

1.18 km from Highland Avenue and Glen Road

Unit-11, 18 Doncrest Road Playter Estates-Danforth, Toronto, ON MLS® E13767584

Residential Condo & Other (Condo Townhouse)

$1350000.0

Price drop by 6.2%

2 +1 Beds
3 Baths
1600-1799 sq-ft

If you have ever considered living in downtown Toronto, steps from everything the city offers, yet still want that leafy green setting to sooth your s

25 Photos

28 Ted Rogers Way, Toronto, ON , MLS #C14156402 , Image - 1

1.26 km from Highland Avenue and Glen Road

28 Ted Rogers Way

Unit-1410, 28 Ted Rogers Way Church-Yonge Corridor, Toronto, ON MLS® C14156402

Residential Condo & Other (Condo Apartment)

$465000.0

1 Beds
1 Baths
500-599 sq-ft

Recent Renovations in the building. Recent paint in the unit. Experience refined urban living in this Monarch-built luxury condo featuring an open-con

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