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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: September 28, 2026

18 Photos

395 Bloor Street S, Toronto, ON , MLS #C13509824 , Image - 1

1.02 km from Highland Avenue and Glen Road

Unit-5501, 395 Bloor Street S North St. James Town, Toronto, ON MLS® C13509824

Residential Condo & Other (Condo Apartment)

$539900.0

1 +1 Beds
1 Baths
600-699 sq-ft

Builder sell! Qualify for Hst Rebate!!!!!Fully furnished model suite by the Developer, this is the builder's inventory brand new unit.Builder's hidden

28 Photos

21 Dale Avenue, Toronto, ON , MLS #C13829546 , Image - 1

0.83 km from Highland Avenue and Glen Road

Unit-502, 21 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C13829546

Residential Condo & Other (Co-op Apartment)

$995000.0

3 Beds
2 Baths
1400-1599 sq-ft

Picture your morning coffee on a private terrace, surrounded by treetops and ravine. That's everyday life in Suite 502, a rare three-bedroom, two-bath

23 Photos

63 Highland Avenue, Toronto, ON , MLS #C13801530 , Image - 1

0.32 km from Highland Avenue and Glen Road

63 Highland Avenue Rosedale-Moore Park, Toronto, ON MLS® C13801530

Residential Freehold (Detached)

$4995000.0

7 Beds
5 Baths
3500-5000 sq-ft

Exceptional Value in Prime Rosedale! this masterfully restored 7-bedroom, 5-bath Arts & Crafts residence presents a rare opportunity to own a timeless

50 Photos

37 St Andrews Gardens, Toronto, ON , MLS #C13799918 , Image - 1

0.52 km from Highland Avenue and Glen Road

37 St Andrews Gardens Rosedale-Moore Park, Toronto, ON MLS® C13799918

Residential Freehold (Detached)

$5600000.0

5 +1 Beds
5 Baths
2500-3000 sq-ft

Newly renovated from top to bottom, this stately five-bedroom residence is set on one of North Rosedale's most private and established streets, offeri

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

17 Photos

127 Roxborough Drive, Toronto, ON , MLS #C13761276 , Image - 1

0.21 km from Highland Avenue and Glen Road

127 Roxborough Drive Rosedale-Moore Park, Toronto, ON MLS® C13761276

Residential Freehold (Detached)

$6480000.0

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

A unique opportunity to achieve your great architectural ambition, to create your own dream home on one of the most prestigious blocks in Canada. This

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

38 Photos

44 Standish Avenue, Toronto, ON , MLS #C13069976 , Image - 1

0.87 km from Highland Avenue and Glen Road

44 Standish Avenue Rosedale-Moore Park, Toronto, ON MLS® C13069976

Residential Freehold (Detached)

$2998000.0

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

*Weekend Open House Saturday September 26th & Sunday September 27th 2-4pm* Fabulous contemporary home! Very spacious, approximately 2,200 square feet

48 Photos

7 Dale Avenue, Toronto, ON , MLS #C13525554 , Image - 1

0.77 km from Highland Avenue and Glen Road

Unit-PH1, 7 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C13525554

Residential Condo & Other (Condo Apartment)

$16500000.0

3 +1 Beds
5 Baths
3750-3999 sq-ft

A truly once-in-a-generation offering, this extraordinary penthouse represents the pinnacle of luxury living. Masterfully designed by internationally

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

48 Photos

149 Roxborough Street E, Toronto, ON , MLS #C13794096 , Image - 1

0.78 km from Highland Avenue and Glen Road

149 Roxborough Street E Rosedale-Moore Park, Toronto, ON MLS® C13794096

Residential Freehold (Detached)

$6999900.0

5 Beds
5 Baths
3000-3500 sq-ft

This is Rosedale Redefined. A full restoration in breathtaking organic modernist design. Natural materials set against a warm, neutral palette, with c

49 Photos

388 Bloor Street E, Toronto, ON , MLS #C13788084 , Image - 1

0.99 km from Highland Avenue and Glen Road

Unit-1801, 388 Bloor Street E Rosedale-Moore Park, Toronto, ON MLS® C13788084

Residential Condo & Other (Condo Apartment)

$799900.0

2 Beds
2 Baths
1000-1199 sq-ft

Rosedale District! Experience bright and spacious living in the prestigious Rosedale Ravine Residences in one of Toronto's highly rated school distric

50 Photos

104 Park Road, Toronto, ON , MLS #C13824430 , Image - 1

0.93 km from Highland Avenue and Glen Road

104 Park Road Rosedale-Moore Park, Toronto, ON MLS® C13824430

Residential Freehold (Detached)

$7500000.0

5 Beds
5 Baths
3000-3500 sq-ft

Originally a stately classic residence, this exceptional Rosedale home was thoughtfully reimagined in 2021 under the direction of acclaimed interior d

21 Photos

21 Dale Avenue, Toronto, ON , MLS #C13686824 , Image - 1

0.83 km from Highland Avenue and Glen Road

Unit-947, 21 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C13686824

Residential Condo & Other (Co-op Apartment)

$995000.0

2 Beds
2 Baths
1000-1199 sq-ft

21 Dale Avenue presents an elevated, maintenance-free lifestyle in the very heart of prime South Rosedale. Set amidst five acres of lush, private ravi

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

24 Photos

135 Roxborough Street E, Toronto, ON , MLS #C13820078 , Image - 1

0.82 km from Highland Avenue and Glen Road

135 Roxborough Street E Rosedale-Moore Park, Toronto, ON MLS® C13820078

Residential Freehold (Semi-Detached )

$3495000.0

4 Beds
3 Baths
3000-3500 sq-ft

Step into refined living within this gracious residence, constructed in 1901 and situated along one of Rosedale's most distinguished addresses, just e

20 Photos

30 Elm Avenue, Toronto, ON , MLS #C13531052 , Image - 1

0.67 km from Highland Avenue and Glen Road

Unit-309, 30 Elm Avenue Rosedale-Moore Park, Toronto, ON MLS® C13531052

Residential Condo & Other (Co-Ownership Apartment)

$749900.0

Price drop by 3.8%

3 Beds
2 Baths
1000-1199 sq-ft

Welcome to Rosedale Court, a hidden gem tucked away on a quiet, tree-lined street in the city's most prestigious neighbourhood of South Rosedale. This

40 Photos

305 Glen Road, Toronto, ON , MLS #C13762770 , Image - 1

0.81 km from Highland Avenue and Glen Road

305 Glen Road Rosedale-Moore Park, Toronto, ON MLS® C13762770

Residential Freehold (Detached)

$3395000.0

5 +1 Beds
5 Baths
2500-3000 sq-ft

A truly luxurious & impeccably crafted detached residence by renowned architect RICHARD WENGLE, gracefully situated within the prestigious enclave of

49 Photos

94 Crescent Road, Toronto, ON , MLS #C13779002 , Image - 1

0.82 km from Highland Avenue and Glen Road

Unit-TH6, 94 Crescent Road Rosedale-Moore Park, Toronto, ON MLS® C13779002

Residential Condo & Other (Condo Townhouse)

$2695000.0

1 +1 Beds
4 Baths
2250-2499 sq-ft

Enchanting South Rosedale boutique townhouse featuring over 2,300 square feet, just steps from Yonge Street. Perfectly tucked away, this bespoke resid

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

15 Photos

28 Linden Street, Toronto, ON , MLS #C13794886 , Image - 1

1.15 km from Highland Avenue and Glen Road

Unit-1006, 28 Linden Street North St. James Town, Toronto, ON MLS® C13794886

Residential Condo & Other (Condo Apartment)

$753000.0

2 Beds
3 Baths
900-999 sq-ft

Welcome to James Cooper Mansion! This bright and spacious 2-bedroom, 2-bathroom suite offers approximately 985 sq. ft. of thoughtfully designed living

44 Photos

7 Dale Avenue, Toronto, ON , MLS #C13449036 , Image - 1

0.77 km from Highland Avenue and Glen Road

Unit-304, 7 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C13449036

Residential Condo & Other (Condo Apartment)

$6499000.0

2 +2 Beds
3 Baths
2500-2749 sq-ft

This is 7 Dale. An extraordinary collection of just 26 residences by Hariri Pontarini and Studio Munge, exemplifying quiet luxury in every thoughtfull

47 Photos

7 Dale Avenue, Toronto, ON , MLS #C13632368 , Image - 1

0.77 km from Highland Avenue and Glen Road

Unit-302, 7 Dale Avenue Rosedale-Moore Park, Toronto, ON MLS® C13632368

Residential Condo & Other (Condo Apartment)

$6749000.0

2 Beds
3 Baths
2750-2999 sq-ft

This is 7 Dale. Just 26 extraordinary residences by Hariri Pontarini & Studio Munge, exemplifying quiet luxury in every flawlessly executed detail. Su

39 Photos

106 Highland Avenue, Toronto, ON , MLS #C13818260 , Image - 1

0.04 km from Highland Avenue and Glen Road

106 Highland Avenue Rosedale-Moore Park, Toronto, ON MLS® C13818260

Residential Freehold (Semi-Detached )

$3750000.0

4 +1 Beds
5 Baths
2500-3000 sq-ft

There's a certain kind of house that feels made for family life, and 106 Highland Avenue is exactly that. Set well back from the street on an exceptio

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

50 Photos

228 Glen Road, Toronto, ON , MLS #C13802198 , Image - 1

0.7 km from Highland Avenue and Glen Road

228 Glen Road Rosedale-Moore Park, Toronto, ON MLS® C13802198

Residential Freehold (Detached)

$5195000.0

4 +1 Beds
5 Baths
2500-3000 sq-ft

A turnkey generational fortress in North Rosedale. Inside, the open-concept layout showcases German wide-plank engineered oak flooring, a 3-story cust

45 Photos

230 Glen Road, Toronto, ON , MLS #C13807498 , Image - 1

0.71 km from Highland Avenue and Glen Road

230 Glen Road Rosedale-Moore Park, Toronto, ON MLS® C13807498

Residential Freehold (Semi-Detached )

$2649000.0

3 Beds
4 Baths
1500-2000 sq-ft

Welcome to 230 Glen Rd, a beautifully updated turn-key property representing an incredible opportunity to establish roots in prestigious Rosedale or d

42 Photos

105 Roxborough Street E, Toronto, ON , MLS #C13820618 , Image - 1

0.87 km from Highland Avenue and Glen Road

105 Roxborough Street E Rosedale-Moore Park, Toronto, ON MLS® C13820618

Residential Freehold (Detached)

$5495000.0

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

Welcome to 105 Roxborough Street East - a Grand Dame of South Rosedale and a rare opportunity to own one of the neighbourhood's magnificent early 1900

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

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

30 Photos

5 Jean Street, Toronto, ON , MLS #C13820574 , Image - 1

0.68 km from Highland Avenue and Glen Road

5 Jean Street Rosedale-Moore Park, Toronto, ON MLS® C13820574

Residential Freehold (Detached)

$2395000.0

4 Beds
4 Baths
2000-2500 sq-ft

Fall in love with life in North Rosedale-where history, prestige, convenience and nature come together in one of Toronto's most treasured neighbourhoo

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

39 Photos

102 Ridge Drive, Toronto, ON , MLS #C13713846 , Image - 1

0.8 km from Highland Avenue and Glen Road

102 Ridge Drive Rosedale-Moore Park, Toronto, ON MLS® C13713846

Residential Freehold (Detached)

$3295000.0

4 +1 Beds
4 Baths
2500-3000 sq-ft

Nestled in the heart of Moore Park, this wonderful 4+1 bedroom family home balances timeless elegance with practical warmth. From the moment you step

35 Photos

70 Summerhill Gardens, Toronto, ON , MLS #C13535582 , Image - 1

1.02 km from Highland Avenue and Glen Road

70 Summerhill Gardens Rosedale-Moore Park, Toronto, ON MLS® C13535582

Residential Freehold (Att/Row/Townhouse)

$1995000.0

2 Beds
2 Baths
1100-1500 sq-ft

Located on an intimate residential street in Summerhill, just steps from Yonge Street's shops, cafés, restaurants and subway, this beautifully designe

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

50 Photos

43 Whitehall Road, Toronto, ON , MLS #C13787722 , Image - 1

0.65 km from Highland Avenue and Glen Road

43 Whitehall Road Rosedale-Moore Park, Toronto, ON MLS® C13787722

Residential Freehold (Detached)

$3999000.0

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 residence with the pedigree of the n

37 Photos

575 Bloor Street E, Toronto, ON , MLS #C13818848 , Image - 1

1.03 km from Highland Avenue and Glen Road

Unit-3405, 575 Bloor Street E North St. James Town, Toronto, ON MLS® C13818848

Residential Condo & Other (Condo Apartment)

$599000.0

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

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395 Bloor Street S

North St. James Town, Toronto, ON

$539900.0

21 Dale Avenue