Skip to main content

Back

Top Areas

Other Areas

Sell Your Home

Shortlisted Properties

New Homes
For Sale
For Rent

Danger! Indicates a dangerous or potentially negative action.

Error

Maximum 4 project can be compared at one go.

House for Sale near Winona Drive and St Clair Avenue West, C02

Showing results 1 - 30 of 30

Explore over 30 houses for sale near Winona Drive and St Clair Avenue West 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 Winona Drive and St Clair Avenue West. Browse through detailed listings with HD images and comprehensive guides. Square Yards Canada makes it easy to find houses for sale near Winona Drive and St Clair Avenue West that are perfect for you.

Last Updated: May 14, 2026

33 Photos

623 Ossington Avenue, Toronto, ON , MLS #C13131154 , Image - 1

2.42 km from Winona Drive and St Clair Avenue West

623 Ossington Avenue Palmerston-Little Italy, Toronto, ON MLS® C13131154

Residential Freehold (Detached)

$1349999.0

4 Beds
2 Baths
1100-1500 sq-ft

Welcome to 623 Ossington Ave, a rarely offered detached Located in the heart of Palmerston-Little Italy, one of Toronto's most desirable neighbourhood

40 Photos

240 Heath Street W, Toronto, ON , MLS #C13130632 , Image - 1

1.69 km from Winona Drive and St Clair Avenue West

Unit-1002, 240 Heath Street W Forest Hill South, Toronto, ON MLS® C13130632

Residential Condo & Other (Condo Apartment)

$2279900.0

2 Beds
2 Baths
1800-1999 sq-ft

***Remarkable Fully Renovated To An Exceptional Standard Unit In One Of The City's Most Exclusive Boutique Building In Forest Hill*This Versatile Plan

28 Photos

317 Lonsdale Road, Toronto, ON , MLS #C13101940 , Image - 1

1.94 km from Winona Drive and St Clair Avenue West

Unit-1B, 317 Lonsdale Road Forest Hill South, Toronto, ON MLS® C13101940

Residential Condo & Other (Condo Apartment)

$1299000.0

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

Sophisticated Living in the Heart of Forest Hill VillageWelcome to this beautifully renovated 1+1 bedroom home, nestled in one of Toronto's most covet

25 Photos

232 St. George Street, Toronto, ON , MLS #C12879008 , Image - 1

2.59 km from Winona Drive and St Clair Avenue West

Unit-19, 232 St. George Street Annex, Toronto, ON MLS® C12879008

Residential Condo & Other (Condo Townhouse)

$1099888.0

Price drop by 6.0%

2 +1 Beds
2 Baths
1000-1199 sq-ft

Discover the charm of Lennox Mews, tucked away from the main road along an enchanting walkway will lead you to Townhouse 19. This beautifully renovate

Pre-Construction

1515 Pickering Parkway

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

32 Photos

280 Howland Avenue, Toronto, ON , MLS #C13114886 , Image - 1

1.78 km from Winona Drive and St Clair Avenue West

Unit-GPH26, 280 Howland Avenue Annex, Toronto, ON MLS® C13114886

Residential Condo & Other (Condo Apartment)

$1398000.0

2 +1 Beds
3 Baths
1000-1199 sq-ft

Welcome to Grand Penthouse 26 at Bianca Condos. This stunning, unique 1,195 sq ft corner suite features 2 bedrooms + den with 3 bathrooms: open concep

33 Photos

499 Palmerston Boulevard, Toronto, ON , MLS #C13113826 , Image - 1

2.52 km from Winona Drive and St Clair Avenue West

499 Palmerston Boulevard Palmerston-Little Italy, Toronto, ON MLS® C13113826

Residential Freehold (Triplex)

$2289000.0

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

Edwardian Triplex on historic Palmerston Boulevard w/incredible 29' x 138' lot and rare private drive! 3 Large self contained suites, all separately m

1 Photos

57 Shanly Street, Toronto, ON

1.82 km from Winona Drive and St Clair Avenue West

57 Shanly Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13044272

Residential Freehold (Duplex)

$1499900.0

5 +1 Beds
3 Baths
1100-1500 sq-ft

The perfect duplex in Dovercourt Village, complete with a basement apartment-offering a total of three self-contained units. This property is full of

46 Photos

434 Westmount Avenue, Toronto, ON , MLS #C13123178 , Image - 1

1.29 km from Winona Drive and St Clair Avenue West

434 Westmount Avenue Oakwood Village, Toronto, ON MLS® C13123178

Residential Freehold (Detached)

$1370000.0

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

Welcome To This Stunning 3-Bedroom, 3-Bathroom Detached Home Offering A Warm And Inviting Ambiance, This Home Is Nestled In One Of Torontos Most Desir

Pre-Construction

Arbor West

Arbor West

10024 Mississauga Road, Brampton

From $559,990

Project Info

88 Buildings
204 Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Caivan

27 Photos

185 Alberta Avenue, Toronto, ON , MLS #C13117134 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-1105, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C13117134

Residential Condo & Other (Condo Apartment)

$2549900.0

3 +1 Beds
4 Baths
2500-2749 sq-ft

An Iconic & Majestic Residence! This 2544 Square Foot, Three-Bedroom + Den Masterpiece In The St. Clair West Village Provides An Unrivaled Living Expe

1 Photos

201 Christie Street, Toronto, ON

1.61 km from Winona Drive and St Clair Avenue West

201 Christie Street Annex, Toronto, ON MLS® C13008902

Residential Freehold (Detached)

$1499999.0

Price drop by 3.2%

4 Beds
3 Baths
1500-2000 sq-ft

Prime Annex Investment Gem - 201 Christie Street, Toronto. Rare detached 2.5-storey home in the prestigious Annex, ideally positioned between Christie

33 Photos

156 Osler Street, Toronto, ON , MLS #W13040610 , Image - 1

2.5 km from Winona Drive and St Clair Avenue West

156 Osler Street Weston-Pellam Park, Toronto, ON MLS® W13040610

Residential Freehold (Semi-Detached )

$799900.0

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

This 2-storey semi-detached home sits on a generous 30-foot lot and features a double car garage via lane access, plus a private front drive. Offering

39 Photos

1410 DUPONT Street, Toronto, ON , MLS #W13119718 , Image - 1

1.89 km from Winona Drive and St Clair Avenue West

Unit-311, 1410 DUPONT Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13119718

Residential Condo & Other (Condo Apartment)

$449900.0

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

Experience Modern Loft-Style Living In The Junction Triangle With This Stunning 1 Bedroom + Study Condo Offering 626 sf Of Thoughtfully Designed Space

Pre-Construction

Corktown Plaza

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

33 Photos

185 Alberta Avenue, Toronto, ON , MLS #C13008270 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-907, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C13008270

Residential Condo & Other (Condo Apartment)

$1123301.0

3 Beds
2 Baths
1200-1399 sq-ft

Welcome to this expansive 3-bedroom, 2-bathroom residence offering approximately 1,300 sq ft of thoughtfully planned living space in the vibrant St. C

26 Photos

185 Alberta Avenue, Toronto, ON , MLS #C12977926 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-1001, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C12977926

Residential Condo & Other (Condo Apartment)

$937900.0

2 +1 Beds
2 Baths
1000-1199 sq-ft

Welcome to Suite 1001, a beautifully appointed 2-bedroom plus den condo offering approximately 1,054 square feet of thoughtfully designed interior liv

41 Photos

185 Alberta Avenue, Toronto, ON , MLS #C13019386 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-807, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C13019386

Residential Condo & Other (Condo Apartment)

$1121900.0

3 Beds
2 Baths
1200-1399 sq-ft

Spacious and beautifully designed 3-bedroom, 2-bathroom suite offering 1,294 square feet in the highly sought-after St. Clair Village community. This

50 Photos

25 Chamberlain Avenue, Toronto, ON , MLS #W13117844 , Image - 1

2.58 km from Winona Drive and St Clair Avenue West

25 Chamberlain Avenue Briar Hill-Belgravia, Toronto, ON MLS® W13117844

Residential Freehold (Duplex)

$1074900.0

4 Beds
2 Baths
700-1100 sq-ft

Duplexes Have More Fun. Investors! House-Hackers! Multi-Generational Families! Welcome to 25 Chamberlain Avenue - a stunning, fully renovated 4-bedroo

Pre-Construction

Lily at Crosstown

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

1 Photos

34 Mc Farland Avenue, Toronto, ON

1.13 km from Winona Drive and St Clair Avenue West

34 Mc Farland Avenue Corso Italia-Davenport, Toronto, ON MLS® W12923854

Residential Freehold (Semi-Detached )

$799000.0

Price drop by 5.9%

4 Beds
2 Baths
1100-1500 sq-ft

Great Starter Home For First Time Buyers, or great investment for investor. Can Be Used As A 4 Bedroom Single-Family Home Or Can Be Used As A Duplex.

13 Photos

1344 Davenport Road, Toronto, ON , MLS #W13110942 , Image - 1

0.77 km from Winona Drive and St Clair Avenue West

1344 Davenport Road Corso Italia-Davenport, Toronto, ON MLS® W13110942

Residential Freehold (Duplex)

$980000.0

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

Great Investment Opportunity Legal Duplex Newly Renovated in High Demand Location, Living/Dining Combination On Main Floor With Hardwood Floorings & B

45 Photos

113 Dupont Street, Toronto, ON , MLS #C12899840 , Image - 1

2.59 km from Winona Drive and St Clair Avenue West

Unit-201, 113 Dupont Street Annex, Toronto, ON MLS® C12899840

Residential Condo & Other (Condo Apartment)

$2485000.0

Price drop by 14.2%

2 Beds
3 Baths
2000-2249 sq-ft

Rarely available designer loft in an intimate boutique building of just seven residences, offering the scale, privacy, and feel of a luxury home in th

48 Photos

221 Dunvegan Road, Toronto, ON , MLS #C13109682 , Image - 1

2.65 km from Winona Drive and St Clair Avenue West

221 Dunvegan Road Forest Hill South, Toronto, ON MLS® C13109682

Residential Freehold (Detached)

$13999000.0

6 +1 Beds
8 Baths
5000 + sq-ft

Introducing 221 Dunvegan Road, an extraordinary Forest Hill residence that captures the essence of modern luxury. Crafted to an exceptional standard b

Pre-Construction

The Clove Condos

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

15 Photos

161 Sellers Avenue, Toronto, ON , MLS #W12864862 , Image - 1

1.29 km from Winona Drive and St Clair Avenue West

161 Sellers Avenue Caledonia-Fairbank, Toronto, ON MLS® W12864862

Residential Freehold (Semi-Detached )

$949900.0

Price drop by 2.6%

3 Beds
2 Baths
1100-1500 sq-ft

Charming & Updated Semi in the Heart of Caledonia-Fairbank. Step into this updated 3-bedroom semi-detached home nestled in one of Toronto's most vibra

40 Photos

165 Caledonia Road, Toronto, ON , MLS #W13103240 , Image - 1

1.92 km from Winona Drive and St Clair Avenue West

165 Caledonia Road Corso Italia-Davenport, Toronto, ON MLS® W13103240

Residential Freehold (Detached)

$1229000.0

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

Welcome to this detached two-storey home in Corso Italia. The front porch offers a nice place to sit and enjoy the neighbourhood. Inside, the main flo

1 Photos

464-468 Winona Drive, Toronto, ON

1.06 km from Winona Drive and St Clair Avenue West

464-468 Winona Drive Oakwood Village, Toronto, ON MLS® C12554262

Residential Freehold (Vacant Land)

$29499000.0

An exceptionally rare opportunity to acquire a premier development site in the heart of Midtown Toronto between Humewood and Cedarvale neighborhoods -

50 Photos

914 Dovercourt Road, Toronto, ON , MLS #W12661820 , Image - 1

1.65 km from Winona Drive and St Clair Avenue West

914 Dovercourt Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12661820

Residential Freehold (Detached)

$1549900.0

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

Live, Rent, or Reimagine-Rare Multi-Unit in Prime West End! Welcome to a fully detached, character-filled home in the heart of Torontos vibrant Doverc

Pre-Construction

The Laurels

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

36 Photos

539 Crawford Street, Toronto, ON , MLS #C13097826 , Image - 1

2.6 km from Winona Drive and St Clair Avenue West

539 Crawford Street Palmerston-Little Italy, Toronto, ON MLS® C13097826

Residential Freehold (Detached)

$3960000.0

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

Welcome to this Jewel Box nested in the heart of Little Italy. This French townhouse-inspired home is filled with luxury details in every corner. With

37 Photos

19 Schell Avenue, Toronto, ON , MLS #W12997840 , Image - 1

2.59 km from Winona Drive and St Clair Avenue West

19 Schell Avenue Briar Hill-Belgravia, Toronto, ON MLS® W12997840

Residential Freehold (Detached)

$1088000.0

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

Feature Sheet Attached! Fully Renovated, Great Floor Plan, Garage and Double Park Driveway With E/V Charger, Walkout To Back Yard Deck,Fully Finished

32 Photos

19 Vesta Drive, Toronto, ON , MLS #C13036918 , Image - 1

1.8 km from Winona Drive and St Clair Avenue West

19 Vesta Drive Forest Hill South, Toronto, ON MLS® C13036918

Residential Freehold (Detached)

$5995000.0

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

Welcome to Toronto's most prestigious neighbourhoods, where timeless elegance and modern sophistication come together in this architectural masterpiec

23 Photos

70 Montclair Avenue W, Toronto, ON , MLS #C12339798 , Image - 1

1.71 km from Winona Drive and St Clair Avenue West

Unit-203, 70 Montclair Avenue W Forest Hill South, Toronto, ON MLS® C12339798

Residential Condo & Other (Condo Apartment)

$1248000.0

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

The Majestic Montclair Is Fit For A Royal! Rarely available 3 bedroom unit plus den in a coveted boutique building in stately Forest Hill Village! Ove

Pre-Construction

The Rebecca Condos

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

41 Photos

444 Roxton Road, Toronto, ON , MLS #C13048352 , Image - 1

2.41 km from Winona Drive and St Clair Avenue West

444 Roxton Road Palmerston-Little Italy, Toronto, ON MLS® C13048352

Residential Freehold (Detached)

$3380000.0

6 +2 Beds
7 Baths
3000-3500 sq-ft

In the heart of the city, yet set within a quiet, tree-lined neighbourhood, this fully renovated 4,200 square foot residence offers the best of both w

19 Photos

1281 Davenport Road, Toronto, ON , MLS #W13086626 , Image - 1

0.81 km from Winona Drive and St Clair Avenue West

1281 Davenport Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13086626

Residential Freehold (Detached)

$890000.0

3 Beds
2 Baths
1500-2000 sq-ft

This well-located detached property offers a fantastic mixed-use investment with a ground-floor convenience store and a spacious 3-bedroom apartment u

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Map View

List View

623 Ossington Avenue, Toronto, ON , MLS #C13131154 , Image - 1

623 Ossington Avenue

Palmerston-Little Italy, Toronto, ON

$1349999.0

240 Heath Street W, Toronto, ON , MLS #C13130632 , Image - 1

240 Heath Street W

Forest Hill South, Toronto, ON

$2279900.0

317 Lonsdale Road, Toronto, ON , MLS #C13101940 , Image - 1

317 Lonsdale Road

Forest Hill South, Toronto, ON

$1299000.0

232 St. George Street, Toronto, ON , MLS #C12879008 , Image - 1

232 St. George Street

Annex, Toronto, ON

$1099888.0

280 Howland Avenue, Toronto, ON , MLS #C13114886 , Image - 1

280 Howland Avenue

Annex, Toronto, ON

$1398000.0

499 Palmerston Boulevard, Toronto, ON , MLS #C13113826 , Image - 1

499 Palmerston Boulevard

Palmerston-Little Italy, Toronto, ON

$2289000.0

57 Shanly Street, Toronto, ON , MLS #W13044272 , Image - 1

57 Shanly Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1499900.0

434 Westmount Avenue, Toronto, ON , MLS #C13123178 , Image - 1

434 Westmount Avenue

Oakwood Village, Toronto, ON

$1370000.0

185 Alberta Avenue, Toronto, ON , MLS #C13117134 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$2549900.0

201 Christie Street, Toronto, ON , MLS #C13008902 , Image - 1

201 Christie Street

Annex, Toronto, ON

$1499999.0

156 Osler Street, Toronto, ON , MLS #W13040610 , Image - 1

156 Osler Street

Weston-Pellam Park, Toronto, ON

$799900.0

1410 DUPONT Street, Toronto, ON , MLS #W13119718 , Image - 1

1410 DUPONT Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$449900.0

185 Alberta Avenue, Toronto, ON , MLS #C13008270 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$1123301.0

185 Alberta Avenue, Toronto, ON , MLS #C12977926 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$937900.0

185 Alberta Avenue, Toronto, ON , MLS #C13019386 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$1121900.0

25 Chamberlain Avenue, Toronto, ON , MLS #W13117844 , Image - 1

25 Chamberlain Avenue

Briar Hill-Belgravia, Toronto, ON

$1074900.0

34 Mc Farland Avenue, Toronto, ON , MLS #W12923854 , Image - 1

34 Mc Farland Avenue

Corso Italia-Davenport, Toronto, ON

$799000.0

1344 Davenport Road, Toronto, ON , MLS #W13110942 , Image - 1

1344 Davenport Road

Corso Italia-Davenport, Toronto, ON

$980000.0

113 Dupont Street, Toronto, ON , MLS #C12899840 , Image - 1

113 Dupont Street

Annex, Toronto, ON

$2485000.0

221 Dunvegan Road, Toronto, ON , MLS #C13109682 , Image - 1

221 Dunvegan Road

Forest Hill South, Toronto, ON

$13999000.0

161 Sellers Avenue, Toronto, ON , MLS #W12864862 , Image - 1

161 Sellers Avenue

Caledonia-Fairbank, Toronto, ON

$949900.0

165 Caledonia Road, Toronto, ON , MLS #W13103240 , Image - 1

165 Caledonia Road

Corso Italia-Davenport, Toronto, ON

$1229000.0

464-468 Winona Drive, Toronto, ON , MLS #C12554262 , Image - 1

464-468 Winona Drive

Oakwood Village, Toronto, ON

$29499000.0

914 Dovercourt Road, Toronto, ON , MLS #W12661820 , Image - 1

914 Dovercourt Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1549900.0

539 Crawford Street, Toronto, ON , MLS #C13097826 , Image - 1

539 Crawford Street

Palmerston-Little Italy, Toronto, ON

$3960000.0

19 Schell Avenue, Toronto, ON , MLS #W12997840 , Image - 1

19 Schell Avenue

Briar Hill-Belgravia, Toronto, ON

$1088000.0

19 Vesta Drive, Toronto, ON , MLS #C13036918 , Image - 1

19 Vesta Drive

Forest Hill South, Toronto, ON

$5995000.0

70 Montclair Avenue W, Toronto, ON , MLS #C12339798 , Image - 1

70 Montclair Avenue W

Forest Hill South, Toronto, ON

$1248000.0

444 Roxton Road, Toronto, ON , MLS #C13048352 , Image - 1

444 Roxton Road

Palmerston-Little Italy, Toronto, ON

$3380000.0

1281 Davenport Road, Toronto, ON , MLS #W13086626 , Image - 1

1281 Davenport Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$890000.0

Related to your search

Top Communities in Toronto

View More

Property Types Available in Toronto

View More

Bedroom Types Available in Toronto

View More

Properties By Budget in Toronto

View More

Top Neighbourhood in Toronto

View More

Nearby Postal Codes of Toronto

View More

Tell us a Little about yourself!