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: November 12, 2026

50 Photos

35 Regal Road, Toronto, ON , MLS #C14091838 , Image - 1

0.62 km from Winona Drive and St Clair Avenue West

35 Regal Road Corso Italia-Davenport, Toronto, ON MLS® C14091838

Residential Freehold (Detached)

$1749988.0

4 +2 Beds
3 Baths
1500-2000 sq-ft

Old Toronto character. Modern updates. City views. A double-car garage. And a neighborhood you'll love coming home to. Welcome to Regal Heights, where

50 Photos

273 Glenholme Avenue, Toronto, ON , MLS #C14162546 , Image - 1

0.87 km from Winona Drive and St Clair Avenue West

273 Glenholme Avenue Oakwood Village, Toronto, ON MLS® C14162546

Residential Freehold (Detached)

$849000.0

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

Cherished For Over 33 Years! This Fully Detached Home In The Desirable Oakwood Village Is A Must See. Expansive Main Floor Layout With Hardwood Floori

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

1 Photos

1204 Ossington Avenue, Toronto, ON

0.72 km from Winona Drive and St Clair Avenue West

1204 Ossington Avenue Wychwood, Toronto, ON MLS® C14145184

Residential Freehold (Duplex)

$408000.0

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

Excellent Opportunity for Renovators, Investors, and Buyers Looking to Customize a Property to Suit Their Own Needs and Vision! This Property Offers G

50 Photos

281 Vaughan Road, Toronto, ON , MLS #C14170110 , Image - 1

1.06 km from Winona Drive and St Clair Avenue West

281 Vaughan Road Humewood-Cedarvale, Toronto, ON MLS® C14170110

Residential Freehold (Detached)

$810000.0

3 Beds
2 Baths
1100-1500 sq-ft

A Familiar Neighbourhood. A New Chapter. There are certain neighbourhoods where the location is what draws you in, and the opportunity to make a home

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

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

48 Photos

43 Marchmount Road, Toronto, ON , MLS #C14171248 , Image - 1

0.83 km from Winona Drive and St Clair Avenue West

43 Marchmount Road Wychwood, Toronto, ON MLS® C14171248

Residential Freehold (Semi-Detached )

$1288000.0

5 Beds
2 Baths
1500-2000 sq-ft

Welcome to this spacious Century Semi Detached Home featuring 5 bedrooms in the highly sought-after Wychwood neighborhood, lovingly maintained by the

22 Photos

409 Melita Crescent, Toronto, ON , MLS #C14114922 , Image - 1

0.9 km from Winona Drive and St Clair Avenue West

409 Melita Crescent Wychwood, Toronto, ON MLS® C14114922

Residential Freehold (Att/Row/Townhouse)

$949000.0

2 Beds
2 Baths
700-1100 sq-ft

Welcome to this renovated freehold end-unit townhouse in the sought-after Wychwood community! Showcasing brand-new luxury vinyl plank flooring, red oa

20 Photos

146 Cedric Avenue, Toronto, ON , MLS #C14170542 , Image - 1

0.96 km from Winona Drive and St Clair Avenue West

146 Cedric Avenue Oakwood Village, Toronto, ON MLS® C14170542

Residential Freehold (Detached)

$719000.0

2 Beds
1 Baths
700-1100 sq-ft

Tucked quietly behind the best stretch of Oakwood Village, this detached 20.5 x 105 ft lot is the ultimate blank canvas with huge potential. Plus, the

40 Photos

185 Cedric Avenue, Toronto, ON , MLS #C14143280 , Image - 1

1.09 km from Winona Drive and St Clair Avenue West

185 Cedric Avenue Oakwood Village, Toronto, ON MLS® C14143280

Residential Freehold (Detached)

$2050000.0

4 Beds
5 Baths
2000-2500 sq-ft

Welcome to an exquisite 4 bed, 5 bath, 3 storey smart home celebrated as the winner of HGTV's Top of the Block and highlighted on Toronto Life's House

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

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

50 Photos

185 Glenholme Avenue, Toronto, ON , MLS #C14170390 , Image - 1

0.57 km from Winona Drive and St Clair Avenue West

185 Glenholme Avenue Oakwood Village, Toronto, ON MLS® C14170390

Residential Freehold (Duplex)

$1899000.0

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

Why choose between a beautiful family home and an income property when you can have both? This rare, fully renovated legal duplex offers the best of b

42 Photos

313 Vaughan Road, Toronto, ON , MLS #C14125296 , Image - 1

1.02 km from Winona Drive and St Clair Avenue West

313 Vaughan Road Humewood-Cedarvale, Toronto, ON MLS® C14125296

Residential Freehold (Detached)

$989900.0

2 +1 Beds
2 Baths
700-1100 sq-ft

Welcome to Tremendous Humewood-Cedarvale, one of Toronto's most sought-after, family-friendly neighbourhoods. This beautifully maintained, fully detac

38 Photos

209 Atlas Avenue, Toronto, ON , MLS #C14030966 , Image - 1

0.86 km from Winona Drive and St Clair Avenue West

209 Atlas Avenue Oakwood Village, Toronto, ON MLS® C14030966

Residential Freehold (Detached)

$1689000.0

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

Skip the bidding war! Here is your chance to purchase this exceptional 3+1 bedroom, 4 bathroom detached home, thoughtfully renovated to the studs and

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

46 Photos

284 Lauder Avenue, Toronto, ON , MLS #C14167320 , Image - 1

0.77 km from Winona Drive and St Clair Avenue West

284 Lauder Avenue Oakwood Village, Toronto, ON MLS® C14167320

Residential Freehold (Detached)

$2649000.0

6 +1 Beds
4 Baths
3000-3500 sq-ft

Welcome to 284 Lauder Avenue! A rare opportunity to own a truly grand and stately character home in a highly desirable, family-friendly neighbourhood.

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

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

45 Photos

402 Salem Avenue N, Toronto, ON , MLS #W14168190 , Image - 1

1.12 km from Winona Drive and St Clair Avenue West

402 Salem Avenue N Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14168190

Residential Freehold (Detached)

$4999000.0

3 Beds
4 Baths
3500-5000 sq-ft

402 Salem Avenue North | A Singular Expression of Art, Architecture & Design More than a hom

36 Photos

132 Marchmount Road, Toronto, ON , MLS #C14140820 , Image - 1

0.69 km from Winona Drive and St Clair Avenue West

132 Marchmount Road Wychwood, Toronto, ON MLS® C14140820

Residential Freehold (Semi-Detached )

$1285000.0

4 Beds
2 Baths
1500-2000 sq-ft

An Incredible Opportunity in Toronto's Sought-After Wychwood Neighbourhood! Offered for the first time in over 60 years, this legal duplex is full of

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

50 Photos

388 Oakwood Avenue, Toronto, ON , MLS #C13649186 , Image - 1

1.01 km from Winona Drive and St Clair Avenue West

388 Oakwood Avenue Oakwood Village, Toronto, ON MLS® C13649186

Residential Freehold (Detached)

$1849999.0

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

Located in the heart of vibrant Oakwood Village, approximately 7 km from the CN Tower, this stunning custom-designed and fully renovated home offers o

14 Photos

60 Greensides Avenue, Toronto, ON , MLS #C13123508 , Image - 1

0.25 km from Winona Drive and St Clair Avenue West

60 Greensides Avenue Wychwood, Toronto, ON MLS® C13123508

Residential Freehold (Detached)

$1050000.0

Price drop by 8.6%

2 Beds
3 Baths
700-1100 sq-ft

Skip the red tape and break ground at 60 Greensides Avenue. This isn't just a property; it's a fully prepped, development site in the heart of Wychwoo

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

149 Atlas Avenue, Toronto, ON

0.66 km from Winona Drive and St Clair Avenue West

149 Atlas Avenue Humewood-Cedarvale, Toronto, ON MLS® C14139554

Residential Freehold (Semi-Detached )

$1299900.0

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

Welcome to 149 Atlas Avenue - a beautifully renovated 3-bedroom, 4-bathroom semi-detached home in sought-after Humewood, fully renovated from top to b

42 Photos

44 Conway Avenue, Toronto, ON , MLS #C13865220 , Image - 1

0.59 km from Winona Drive and St Clair Avenue West

44 Conway Avenue Oakwood Village, Toronto, ON MLS® C13865220

Residential Freehold (Detached)

$919000.0

Price drop by 6.2%

3 Beds
2 Baths
700-1100 sq-ft

Charming Detached Bungalow with Endless Potential in Vibrant Oakwood Village! *Welcome to this 3-bedroom, 2-washroom detached bungalow situated on an

34 Photos

858 Dupont Street, Toronto, ON , MLS #W14122598 , Image - 1

1.13 km from Winona Drive and St Clair Avenue West

Unit-PH12, 858 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14122598

Residential Condo & Other (Condo Apartment)

$870796.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to Penthouse 12 at The Dupont, a masterfully designed penthouse retreat offering 829 square feet of light-filled interior living space in one

Open House : Sat Nov 14, 12:00 PM to 04:00 PM

35 Photos

530 St Clair Avenue W, Toronto, ON , MLS #C14087182 , Image - 1

1.1 km from Winona Drive and St Clair Avenue West

Unit-1401, 530 St Clair Avenue W Humewood-Cedarvale, Toronto, ON MLS® C14087182

Residential Condo & Other (Condo Apartment)

$599000.0

Price drop by 3.2%

1 +1 Beds
1 Baths
700-799 sq-ft

Bright & spacious one bedroom plus den in a fantastic midtown location. Clear west-facing windows and a large balcony bring in great natural light and

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

39 Photos

279 Lauder Avenue, Toronto, ON , MLS #C13751852 , Image - 1

0.74 km from Winona Drive and St Clair Avenue West

279 Lauder Avenue Oakwood Village, Toronto, ON MLS® C13751852

Residential Freehold (Duplex)

$1345000.0

Price drop by 3.6%

6 Beds
4 Baths
1500-2000 sq-ft

An excellent opportunity to acquire a well-performing multi-residential property in Toronto's evolving and highly desirable Oakwood Village neighbourh

32 Photos

858 DuPont Street, Toronto, ON , MLS #W14144656 , Image - 1

1.13 km from Winona Drive and St Clair Avenue West

Unit-724, 858 DuPont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14144656

Residential Condo & Other (Condo Apartment)

$901770.0

3 Beds
2 Baths
1000-1199 sq-ft

A fresh take on west-end living awaits at The Dupont by Tridel. Set at Dupont and Ossington, this three-bedroom, two-bathroom residence pairs contempo

43 Photos

1045 Ossington Avenue, Toronto, ON , MLS #W14097978 , Image - 1

1.19 km from Winona Drive and St Clair Avenue West

1045 Ossington Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14097978

Residential Freehold (Semi-Detached )

$999900.0

4 Beds
2 Baths
1500-2000 sq-ft

OFFERS ANYTIME! Welcome To 1045 Ossington Ave! This Beautifully Renovated Home Has Been Thoughtfully And Tastefully Updated Throughout, Blending Moder

28 Photos

55 Oakwood Avenue, Toronto, ON , MLS #C14142454 , Image - 1

0.48 km from Winona Drive and St Clair Avenue West

55 Oakwood Avenue Wychwood, Toronto, ON MLS® C14142454

Residential Freehold (Detached)

$1225000.0

6 Beds
4 Baths
2500-3000 sq-ft

Offered for the first time in decades, this distinguished Wychwood/Regal Heights detach home presents a remarkable opportunity to own a property with

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

20 Photos

248 Benson Avenue, Toronto, ON , MLS #C14098898 , Image - 1

0.17 km from Winona Drive and St Clair Avenue West

248 Benson Avenue Wychwood, Toronto, ON MLS® C14098898

Residential Freehold (Semi-Detached )

$1149900.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to 248 Benson Ave, a rare turnkey opportunity in the sought-after Wychwood neighborhood. Redesigned by owner-architect and renovated from the

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

50 Photos

174 Cedric Avenue, Toronto, ON , MLS #C14131246 , Image - 1

1.04 km from Winona Drive and St Clair Avenue West

174 Cedric Avenue Oakwood Village, Toronto, ON MLS® C14131246

Residential Freehold (Detached)

$2785000.0

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

Step into luxurious urban living with this stunning property Located in Toronto's vibrant St Clair West neighbourhood. Inspired by trendy Modern Organ

11 Photos

858 Dupont Street, Toronto, ON , MLS #W14140112 , Image - 1

1.14 km from Winona Drive and St Clair Avenue West

Unit-313, 858 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14140112

Residential Condo & Other (Condo Apartment)

$539000.0

1 Beds
1 Baths
500-599 sq-ft

Exceptional Condo Living. An Incredible Neighbourhood. The Tridel Difference.Welcome to The Dupont, a stunning new condominium community by Tridel, on

27 Photos

185 Alberta Avenue, Toronto, ON , MLS #C13515804 , Image - 1

0.1 km from Winona Drive and St Clair Avenue West

Unit-810, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C13515804

Residential Condo & Other (Condo Apartment)

$568000.0

Price drop by 2.9%

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

Beautiful upgrade unit! 1 bed + den (Den separate room with sliding doors & wood floor can be used as a 2nd bedroom )+ rarely found Sunny West exposur

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

50 Photos

311 Wychwood Avenue, Toronto, ON , MLS #C14158754 , Image - 1

1.01 km from Winona Drive and St Clair Avenue West

311 Wychwood Avenue Humewood-Cedarvale, Toronto, ON MLS® C14158754

Residential Freehold (Detached)

$2249000.0

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

Welcome to this exceptionally crafted, Detached 4+1 Bedroom, 6 Baths Residence offering the perfect blend of luxury and functional family living in Hu

33 Photos

858 Dupont Street, Toronto, ON , MLS #W14156684 , Image - 1

1.13 km from Winona Drive and St Clair Avenue West

Unit-Ph39, 858 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14156684

Residential Condo & Other (Condo Apartment)

$769000.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to Penthouse 39 at Tridel's The Dupont, a newly completed boutique mid-rise residence at Dupont and Ossington! Brand new and never lived in, t

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Map View

List View

35 Regal Road, Toronto, ON , MLS #C14091838 , Image - 1

35 Regal Road

Corso Italia-Davenport, Toronto, ON

$1749988.0

273 Glenholme Avenue, Toronto, ON , MLS #C14162546 , Image - 1

273 Glenholme Avenue

Oakwood Village, Toronto, ON

$849000.0

1204 Ossington Avenue, Toronto, ON , MLS #C14145184 , Image - 1

1204 Ossington Avenue

Wychwood, Toronto, ON

$408000.0

281 Vaughan Road, Toronto, ON , MLS #C14170110 , Image - 1

281 Vaughan Road

Humewood-Cedarvale, Toronto, ON

$810000.0

43 Marchmount Road, Toronto, ON , MLS #C14171248 , Image - 1

43 Marchmount Road

Wychwood, Toronto, ON

$1288000.0

409 Melita Crescent, Toronto, ON , MLS #C14114922 , Image - 1

409 Melita Crescent

Wychwood, Toronto, ON

$949000.0

146 Cedric Avenue, Toronto, ON , MLS #C14170542 , Image - 1

146 Cedric Avenue

Oakwood Village, Toronto, ON

$719000.0

185 Cedric Avenue, Toronto, ON , MLS #C14143280 , Image - 1

185 Cedric Avenue

Oakwood Village, Toronto, ON

$2050000.0

185 Glenholme Avenue, Toronto, ON , MLS #C14170390 , Image - 1

185 Glenholme Avenue

Oakwood Village, Toronto, ON

$1899000.0

313 Vaughan Road, Toronto, ON , MLS #C14125296 , Image - 1

313 Vaughan Road

Humewood-Cedarvale, Toronto, ON

$989900.0

209 Atlas Avenue, Toronto, ON , MLS #C14030966 , Image - 1

209 Atlas Avenue

Oakwood Village, Toronto, ON

$1689000.0

284 Lauder Avenue, Toronto, ON , MLS #C14167320 , Image - 1

284 Lauder Avenue

Oakwood Village, Toronto, ON

$2649000.0

402 Salem Avenue N, Toronto, ON , MLS #W14168190 , Image - 1

402 Salem Avenue N

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$4999000.0

132 Marchmount Road, Toronto, ON , MLS #C14140820 , Image - 1

132 Marchmount Road

Wychwood, Toronto, ON

$1285000.0

388 Oakwood Avenue, Toronto, ON , MLS #C13649186 , Image - 1

388 Oakwood Avenue

Oakwood Village, Toronto, ON

$1849999.0

60 Greensides Avenue, Toronto, ON , MLS #C13123508 , Image - 1

60 Greensides Avenue

Wychwood, Toronto, ON

$1050000.0

149 Atlas Avenue, Toronto, ON , MLS #C14139554 , Image - 1

149 Atlas Avenue

Humewood-Cedarvale, Toronto, ON

$1299900.0

44 Conway Avenue, Toronto, ON , MLS #C13865220 , Image - 1

44 Conway Avenue

Oakwood Village, Toronto, ON

$919000.0

858 Dupont Street, Toronto, ON , MLS #W14122598 , Image - 1

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$870796.0

530 St Clair Avenue W, Toronto, ON , MLS #C14087182 , Image - 1

530 St Clair Avenue W

Humewood-Cedarvale, Toronto, ON

$599000.0

279 Lauder Avenue, Toronto, ON , MLS #C13751852 , Image - 1

279 Lauder Avenue

Oakwood Village, Toronto, ON

$1345000.0

858 DuPont Street, Toronto, ON , MLS #W14144656 , Image - 1

858 DuPont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$901770.0

1045 Ossington Avenue, Toronto, ON , MLS #W14097978 , Image - 1

1045 Ossington Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$999900.0

55 Oakwood Avenue, Toronto, ON , MLS #C14142454 , Image - 1

55 Oakwood Avenue

Wychwood, Toronto, ON

$1225000.0

248 Benson Avenue, Toronto, ON , MLS #C14098898 , Image - 1

248 Benson Avenue

Wychwood, Toronto, ON

$1149900.0

174 Cedric Avenue, Toronto, ON , MLS #C14131246 , Image - 1

174 Cedric Avenue

Oakwood Village, Toronto, ON

$2785000.0

858 Dupont Street, Toronto, ON , MLS #W14140112 , Image - 1

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$539000.0

185 Alberta Avenue, Toronto, ON , MLS #C13515804 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$568000.0

311 Wychwood Avenue, Toronto, ON , MLS #C14158754 , Image - 1

311 Wychwood Avenue

Humewood-Cedarvale, Toronto, ON

$2249000.0

858 Dupont Street, Toronto, ON , MLS #W14156684 , Image - 1

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$769000.0

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!