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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: September 27, 2026

50 Photos

1069 Davenport Road, Toronto, ON , MLS #C13832350 , Image - 1

0.74 km from Winona Drive and St Clair Avenue West

1069 Davenport Road Wychwood, Toronto, ON MLS® C13832350

Residential Freehold (Semi-Detached )

$1380000.0

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

Welcome to 1069 Davenport Rd. with large enclosed porch. 3 + 1 bedrooms, 2 bathroom home has been freshly painted and features new laminate flooring

38 Photos

61 Appleton Avenue, Toronto, ON , MLS #C13824332 , Image - 1

0.45 km from Winona Drive and St Clair Avenue West

61 Appleton Avenue Oakwood Village, Toronto, ON MLS® C13824332

Residential Freehold (Semi-Detached )

$1399000.0

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

61 Appleton is a meticulously updated, move-in-ready semi-detached 3-storey home in the family-friendly Oakwood-Vaughan neighbourhood! This versatile

32 Photos

303 Oakwood Avenue, Toronto, ON , MLS #C13831764 , Image - 1

0.69 km from Winona Drive and St Clair Avenue West

303 Oakwood Avenue Oakwood Village, Toronto, ON MLS® C13831764

Residential Freehold (Semi-Detached )

$1069000.0

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

Semi-Detached In One Of Toronto's Great Neighbourhoods, Fronting across from park Park. Clear View. Bus At Front Steps, 3 Spacious Units, With A Great

49 Photos

396 Bartlett Avenue N, Toronto, ON , MLS #W13831048 , Image - 1

1.01 km from Winona Drive and St Clair Avenue West

396 Bartlett Avenue N Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13831048

Residential Freehold (Detached)

$1249000.0

5 Beds
2 Baths
2000-2500 sq-ft

Some homes are all about the neighbourhood, and 396 Bartlett Avenue North puts you right in the middle of one worth discovering. Geary Avenue is just

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

13 Photos

285 Robina Avenue, Toronto, ON , MLS #C13792980 , Image - 1

1.13 km from Winona Drive and St Clair Avenue West

285 Robina Avenue Oakwood Village, Toronto, ON MLS® C13792980

Residential Freehold (Semi-Detached )

$750000.0

2 Beds
2 Baths
700-1100 sq-ft

Don't miss this rare opportunity to own a stylish, move-in-ready 2-bedroom bungalow on a quiet, tree-lined street in vibrant Oakwood Village! Perfect

25 Photos

59 Cherrywood Avenue, Toronto, ON , MLS #C13741578 , Image - 1

0.9 km from Winona Drive and St Clair Avenue West

59 Cherrywood Avenue Humewood-Cedarvale, Toronto, ON MLS® C13741578

Residential Freehold (Detached)

$1288800.0

3 Beds
2 Baths
1100-1500 sq-ft

Waiting to get into The Woods community? Now is your chance!!! Get ready to do some creative design work with this solid detached 2-storey brick house

41 Photos

89 Regal Road, Toronto, ON , MLS #W13828862 , Image - 1

0.87 km from Winona Drive and St Clair Avenue West

89 Regal Road Corso Italia-Davenport, Toronto, ON MLS® W13828862

Residential Freehold (Detached)

$4750000.0

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

Vibrant new construction home with panoramic views from all levels. Three large terraces and multiple walkouts! Heated floors, Elevator, Home autom

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)

$575000.0

Price drop by 1.7%

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

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

8 Photos

840 St Clair Avenue W, Toronto, ON , MLS #C13826248 , Image - 1

0.07 km from Winona Drive and St Clair Avenue West

Unit-205, 840 St Clair Avenue W Oakwood Village, Toronto, ON MLS® C13826248

Residential Condo & Other (Condo Apartment)

$500000.0

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

Welcome To Your Urban Oasis At 840 St. Clair West! This Stylish 1 Bedroom + Den Boutique Condo Offers Modern Design, Functionality, And An Unbeatable

39 Photos

91 Maplewood Avenue, Toronto, ON , MLS #C13818410 , Image - 1

0.88 km from Winona Drive and St Clair Avenue West

91 Maplewood Avenue Humewood-Cedarvale, Toronto, ON MLS® C13818410

Residential Freehold (Semi-Detached )

$1089000.0

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

From the Street, a Handsome Traditional Facade Gives Little Away. Step Inside and an Entirely Different Experience Unfolds. Thoughtfully Conceived by

28 Photos

47 Hocken Avenue, Toronto, ON , MLS #C13821060 , Image - 1

0.98 km from Winona Drive and St Clair Avenue West

47 Hocken Avenue Wychwood, Toronto, ON MLS® C13821060

Residential Freehold (Semi-Detached )

$999000.0

3 Beds
2 Baths
700-1100 sq-ft

A rare opportunity for first-time buyers to get into the market without compromising on location. Welcome to this charming, move-in-ready home in the

42 Photos

87 Winnett Avenue, Toronto, ON , MLS #C13819878 , Image - 1

0.68 km from Winona Drive and St Clair Avenue West

87 Winnett Avenue Oakwood Village, Toronto, ON MLS® C13819878

Residential Freehold (Semi-Detached )

$1395000.0

3 Beds
3 Baths
1100-1500 sq-ft

A winner on Winnett! This beautifully renovated 3-bedroom, 3-bathroom home, including a convenient main floor powder room, blends thoughtful design wi

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

29 Photos

313 Glenholme Avenue, Toronto, ON , MLS #C13826346 , Image - 1

0.99 km from Winona Drive and St Clair Avenue West

313 Glenholme Avenue Oakwood Village, Toronto, ON MLS® C13826346

Residential Freehold (Detached)

$899000.0

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

A detached Oakwood Village home that adapts to the way you want to live. Today it is three self-contained units, each with a private entrance, and it

29 Photos

80 Wychwood Park, Toronto, ON , MLS #C13819668 , Image - 1

1.13 km from Winona Drive and St Clair Avenue West

80 Wychwood Park Wychwood, Toronto, ON MLS® C13819668

Residential Freehold (Multiplex)

$6900000.0

7 +1 Beds
5 Baths
5000 + sq-ft

The Magic of Wychwood Park. Wychwood Park stands as one of the most unique and transformative enclaves in the country. Conceived as an artistic haven

42 Photos

180 Atlas Avenue, Toronto, ON , MLS #C13811062 , Image - 1

0.71 km from Winona Drive and St Clair Avenue West

180 Atlas Avenue Oakwood Village, Toronto, ON MLS® C13811062

Residential Freehold (Detached)

$1149000.0

3 Beds
2 Baths
1100-1500 sq-ft

Attention End Users, Builders & Investors - A Rare 25 x 120 Lot in the Humewood Public School Catchment. For close to six decades, this home has been

15 Photos

26 Geary Avenue, Toronto, ON , MLS #C13796666 , Image - 1

0.99 km from Winona Drive and St Clair Avenue West

26 Geary Avenue Wychwood, Toronto, ON MLS® C13796666

Residential Freehold (Detached)

$949000.0

3 Beds
3 Baths
1100-1500 sq-ft

Great Opportunity in the Geary Avenue Area. Located near Dupont Street and Ossington Avenue, this property is currently configured as a duplex and fea

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

39 Photos

858 Dupont Street, Toronto, ON , MLS #W13823704 , Image - 1

1.11 km from Winona Drive and St Clair Avenue West

Unit-224, 858 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13823704

Residential Condo & Other (Condo Apartment)

$1185000.0

3 Beds
2 Baths
1000-1199 sq-ft

Rarely Offered At The Dupont By Tridel! This Luxury Boutique Residence Offers 1,010 Sq. Ft. Of Interior Living Space Plus An Incredible 468 Sq. Ft. Pr

47 Photos

16 Hector Avenue, Toronto, ON , MLS #C13784156 , Image - 1

0.92 km from Winona Drive and St Clair Avenue West

16 Hector Avenue Wychwood, Toronto, ON MLS® C13784156

Residential Freehold (Semi-Detached )

$1399000.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to this charming 3-bedroom, 2-bathroom semi-detached home tucked away on one of Wychwood's most welcoming and family-oriented streets. Set on

31 Photos

67 Oakwood Avenue, Toronto, ON , MLS #C13632422 , Image - 1

0.44 km from Winona Drive and St Clair Avenue West

67 Oakwood Avenue Wychwood, Toronto, ON MLS® C13632422

Residential Freehold (Detached)

$1758000.0

Price drop by 7.5%

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

Exceptional Detached Residence In Wychwood/Regal Heights. This Character-Filled Property Offers Outstanding Versatility For Families, Investors, Or Th

12 Photos

29 Northcliffe Boulevard, Toronto, ON , MLS #W13767436 , Image - 1

0.74 km from Winona Drive and St Clair Avenue West

29 Northcliffe Boulevard Corso Italia-Davenport, Toronto, ON MLS® W13767436

Residential Freehold (Detached)

$2199000.0

5 Beds
4 Baths
2000-2500 sq-ft

Welcome to 29 Northcliffe Blvd, a meticulously maintained, owner-occupied detached 3-storey home tucked into one ofRegal Heights' most sought-after st

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

38 Photos

82 Helena Avenue, Toronto, ON , MLS #C13780896 , Image - 1

0.91 km from Winona Drive and St Clair Avenue West

82 Helena Avenue Wychwood, Toronto, ON MLS® C13780896

Residential Freehold (Semi-Detached )

$1729000.0

4 Beds
2 Baths
1500-2000 sq-ft

Tremendous opportunity to transform this 2,750 sq ft space into the home of your dreams! Set on an impressive lot with a double-car garage and a subst

28 Photos

364 Winona Drive, Toronto, ON , MLS #C13821002 , Image - 1

0.65 km from Winona Drive and St Clair Avenue West

364 Winona Drive Oakwood Village, Toronto, ON MLS® C13821002

Residential Freehold (Detached)

$579000.0

2 Beds
1 Baths
< 700 sq-ft

A fantastic opportunity to own a well-located condo alternative in the heart of the city, nestled in the thriving, family-friendly Humewood-Cedarvale

46 Photos

237 Melita Avenue, Toronto, ON , MLS #C13800698 , Image - 1

1.12 km from Winona Drive and St Clair Avenue West

237 Melita Avenue Wychwood, Toronto, ON MLS® C13800698

Residential Freehold (Semi-Detached )

$1749000.0

5 +0 Beds
4 Baths
2000-2500 sq-ft

Welcome to 237 Melita Avenue, a professionally designed 3-story, 5-bedroom masterpiece with finished basement completely gutted and rebuilt from top t

38 Photos

209 Atlas Avenue, Toronto, ON , MLS #C13752386 , Image - 1

0.86 km from Winona Drive and St Clair Avenue West

209 Atlas Avenue Oakwood Village, Toronto, ON MLS® C13752386

Residential Freehold (Detached)

$1739000.0

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

Welcome to this exceptional 3+1 bedroom, 4 bathroom detached home, thoughtfully renovated to the studs and designed for effortless family living and e

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

14 Photos

15 Maplewood Avenue, Toronto, ON , MLS #C13649048 , Image - 1

1.08 km from Winona Drive and St Clair Avenue West

Unit-310, 15 Maplewood Avenue Humewood-Cedarvale, Toronto, ON MLS® C13649048

Residential Condo & Other (Condo Apartment)

$315000.0

1 Beds
1 Baths
0-499 sq-ft

A bright BEAUTIFUL, sun-filled southwest-facing 1-bedroom condo in the heart of St. Clair West! Featuring a functional open-concept layout, upgraded k

6 Photos

1259 Davenport Road, Toronto, ON , MLS #W13815862 , Image - 1

0.76 km from Winona Drive and St Clair Avenue West

1259 Davenport Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13815862

Residential Freehold (Att/Row/Townhouse)

$924990.0

5 +1 Beds
2 Baths
1500-2000 sq-ft

A Two-Unit Property Opportunity in Toronto! Investors and house hackers, discover 1259 Davenport Rd, a substantial 3-storey freehold townhome offering

18 Photos

1390 Davenport Road, Toronto, ON , MLS #W13815490 , Image - 1

0.88 km from Winona Drive and St Clair Avenue West

1390 Davenport Road Corso Italia-Davenport, Toronto, ON MLS® W13815490

Residential Freehold (Semi-Detached )

$699000.0

3 Beds
1 Baths
700-1100 sq-ft

An exciting opportunity to renovate, reimagine, and create your own city haven at 1390 Davenport Road. This 3-bedroom semi-detached home offers incred

41 Photos

131 Lauder Avenue, Toronto, ON , MLS #W13693722 , Image - 1

0.59 km from Winona Drive and St Clair Avenue West

131 Lauder Avenue Wychwood, Toronto, ON MLS® W13693722

Residential Freehold (Duplex)

$1479000.0

Price drop by 4.5%

5 Beds
4 Baths
2000-2500 sq-ft

A grand dame with undeniable charm and exceptional potential, this home makes a memorable first impression with its handsome presence and great curb a

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

33 Photos

1169 Davenport Road, Toronto, ON , MLS #C13814814 , Image - 1

0.65 km from Winona Drive and St Clair Avenue West

1169 Davenport Road Wychwood, Toronto, ON MLS® C13814814

Residential Freehold (Fourplex)

$2995000.0

4 +4 Beds
11 Baths
3000-3500 sq-ft

Newly built, thoughtfully designed residence offering a rare opportunity to own a multi-suite property with over 4,402 sq ft., comprised of four spaci

28 Photos

153 Lambertlodge Avenue, Toronto, ON , MLS #C13813094 , Image - 1

0.95 km from Winona Drive and St Clair Avenue West

153 Lambertlodge Avenue Wychwood, Toronto, ON MLS® C13813094

Residential Freehold (Att/Row/Townhouse)

$899000.0

3 Beds
2 Baths
1100-1500 sq-ft

End-of-row charm with the feel of a semi in one of the city's most family-friendly neighbourhoods! Park and a playground are right outside your door,

Shortlisted Properties

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Maximum 4 project can be compared at one go.

Map View

List View

1069 Davenport Road, Toronto, ON , MLS #C13832350 , Image - 1

1069 Davenport Road

Wychwood, Toronto, ON

$1380000.0

61 Appleton Avenue, Toronto, ON , MLS #C13824332 , Image - 1

61 Appleton Avenue

Oakwood Village, Toronto, ON

$1399000.0

303 Oakwood Avenue, Toronto, ON , MLS #C13831764 , Image - 1

303 Oakwood Avenue

Oakwood Village, Toronto, ON

$1069000.0

396 Bartlett Avenue N, Toronto, ON , MLS #W13831048 , Image - 1

396 Bartlett Avenue N

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1249000.0

285 Robina Avenue, Toronto, ON , MLS #C13792980 , Image - 1

285 Robina Avenue

Oakwood Village, Toronto, ON

$750000.0

59 Cherrywood Avenue, Toronto, ON , MLS #C13741578 , Image - 1

59 Cherrywood Avenue

Humewood-Cedarvale, Toronto, ON

$1288800.0

89 Regal Road, Toronto, ON , MLS #W13828862 , Image - 1

89 Regal Road

Corso Italia-Davenport, Toronto, ON

$4750000.0

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

185 Alberta Avenue

Oakwood Village, Toronto, ON

$575000.0

840 St Clair Avenue W, Toronto, ON , MLS #C13826248 , Image - 1

840 St Clair Avenue W

Oakwood Village, Toronto, ON

$500000.0

91 Maplewood Avenue, Toronto, ON , MLS #C13818410 , Image - 1

91 Maplewood Avenue

Humewood-Cedarvale, Toronto, ON

$1089000.0

47 Hocken Avenue, Toronto, ON , MLS #C13821060 , Image - 1

47 Hocken Avenue

Wychwood, Toronto, ON

$999000.0

87 Winnett Avenue, Toronto, ON , MLS #C13819878 , Image - 1

87 Winnett Avenue

Oakwood Village, Toronto, ON

$1395000.0

313 Glenholme Avenue, Toronto, ON , MLS #C13826346 , Image - 1

313 Glenholme Avenue

Oakwood Village, Toronto, ON

$899000.0

80 Wychwood Park, Toronto, ON , MLS #C13819668 , Image - 1

80 Wychwood Park

Wychwood, Toronto, ON

$6900000.0

180 Atlas Avenue, Toronto, ON , MLS #C13811062 , Image - 1

180 Atlas Avenue

Oakwood Village, Toronto, ON

$1149000.0

26 Geary Avenue, Toronto, ON , MLS #C13796666 , Image - 1

26 Geary Avenue

Wychwood, Toronto, ON

$949000.0

858 Dupont Street, Toronto, ON , MLS #W13823704 , Image - 1

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1185000.0

16 Hector Avenue, Toronto, ON , MLS #C13784156 , Image - 1

16 Hector Avenue

Wychwood, Toronto, ON

$1399000.0

67 Oakwood Avenue, Toronto, ON , MLS #C13632422 , Image - 1

67 Oakwood Avenue

Wychwood, Toronto, ON

$1758000.0

29 Northcliffe Boulevard, Toronto, ON , MLS #W13767436 , Image - 1

29 Northcliffe Boulevard

Corso Italia-Davenport, Toronto, ON

$2199000.0

82 Helena Avenue, Toronto, ON , MLS #C13780896 , Image - 1

82 Helena Avenue

Wychwood, Toronto, ON

$1729000.0

364 Winona Drive, Toronto, ON , MLS #C13821002 , Image - 1

364 Winona Drive

Oakwood Village, Toronto, ON

$579000.0

237 Melita Avenue, Toronto, ON , MLS #C13800698 , Image - 1

237 Melita Avenue

Wychwood, Toronto, ON

$1749000.0

209 Atlas Avenue, Toronto, ON , MLS #C13752386 , Image - 1

209 Atlas Avenue

Oakwood Village, Toronto, ON

$1739000.0

15 Maplewood Avenue, Toronto, ON , MLS #C13649048 , Image - 1

15 Maplewood Avenue

Humewood-Cedarvale, Toronto, ON

$315000.0

1259 Davenport Road, Toronto, ON , MLS #W13815862 , Image - 1

1259 Davenport Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$924990.0

1390 Davenport Road, Toronto, ON , MLS #W13815490 , Image - 1

1390 Davenport Road

Corso Italia-Davenport, Toronto, ON

$699000.0

131 Lauder Avenue, Toronto, ON , MLS #W13693722 , Image - 1

131 Lauder Avenue

Wychwood, Toronto, ON

$1479000.0

1169 Davenport Road, Toronto, ON , MLS #C13814814 , Image - 1

1169 Davenport Road

Wychwood, Toronto, ON

$2995000.0

153 Lambertlodge Avenue, Toronto, ON , MLS #C13813094 , Image - 1

153 Lambertlodge Avenue

Wychwood, Toronto, ON

$899000.0

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