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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: March 30, 2026

35 Photos

1787 ST. CLAIR Avenue W, Toronto, ON , MLS #W12910682 , Image - 1

2.5 km from Winona Drive and St Clair Avenue West

Unit-609, 1787 ST. CLAIR Avenue W Weston-Pellam Park, Toronto, ON MLS® W12910682

Residential Condo & Other (Condo Apartment)

$529900.0

Price drop by 3.6%

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

2 yr new 1Bed + Den Condo(570 sqft interior plus 45sqft balcony) facing west with Parking and Locker Included in the vibrant and trendy neighborhood

35 Photos

707 Eglinton Avenue W, Toronto, ON , MLS #C12747422 , Image - 1

2.56 km from Winona Drive and St Clair Avenue West

Unit-604, 707 Eglinton Avenue W Forest Hill South, Toronto, ON MLS® C12747422

Residential Condo & Other (Co-Ownership Apartment)

$799000.0

2 Beds
1 Baths
1000-1199 sq-ft

WELCOME TO THE ROYCROFT (circa 1939) a rare Art Deco gem designed by prominent architect John Edward Hoare, The Roycroft is a New York-style co-owners

13 Photos

1344 Davenport Road, Toronto, ON , MLS #W12632060 , Image - 1

0.77 km from Winona Drive and St Clair Avenue West

1344 Davenport Road Corso Italia-Davenport, Toronto, ON MLS® W12632060

Residential Freehold (Duplex)

$688888.0

Price drop by 22.5%

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

41 Photos

49 Osler Street, Toronto, ON , MLS #W12917670 , Image - 1

2.54 km from Winona Drive and St Clair Avenue West

49 Osler Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12917670

Residential Freehold (Semi-Detached )

$1089000.0

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

STOP SCROLLING: YOUR JUNCTION TRIANGLE GLOW-UP IS HERE. This is a move-in-ready Semi that actually lives up to the hype. For first-timers and young f

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

35 Photos

3 Silverwood Avenue, Toronto, ON , MLS #C12586536 , Image - 1

2.17 km from Winona Drive and St Clair Avenue West

3 Silverwood Avenue Forest Hill South, Toronto, ON MLS® C12586536

Residential Freehold (Detached)

$3880000.0

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

Rarely Offered! Stunning 4+1 Bed, 5 Bath Residence In Coveted Forest Hill Village On A Quiet, Tree-Lined Street. Approx. 4,500 Sqft Of Total Living Sp

47 Photos

1 Burton Road, Toronto, ON , MLS #C12927954 , Image - 1

1.96 km from Winona Drive and St Clair Avenue West

1 Burton Road Forest Hill South, Toronto, ON MLS® C12927954

Residential Freehold (Detached)

$5395000.0

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

This exceptional residence, custom-designed in 2000 by the esteemed firm of Katharine Newman and Peter Cebulak, exemplifies luxurious living with the

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 )

$849000.0

4 Beds
2 Baths
1100-1500 sq-ft

This Two-Story Duplex Can Easily Be Converted Back To A Single-Family Home Or Kept As Two Large 2 Bedroom Units To Live In Or Rent Out. The Central Lo

45 Photos

342 Spadina Road, Toronto, ON , MLS #C12655918 , Image - 1

2.25 km from Winona Drive and St Clair Avenue West

Unit-405, 342 Spadina Road Forest Hill South, Toronto, ON MLS® C12655918

Residential Condo & Other (Condo Apartment)

$3075000.0

Price drop by 3.9%

2 +1 Beds
2 Baths
2500-2749 sq-ft

Welcome to Suite 405 at 342 Spadina Road, where luxury and comfort meet in the heart of Forest Hill South. This exquisite 2,534 sq. ft. condo includin

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

388 Oakwood Avenue, Toronto, ON , MLS #C12357463 , Image - 1

1.01 km from Winona Drive and St Clair Avenue West

388 Oakwood Avenue Oakwood Village, Toronto, ON MLS® C12357463

Residential Freehold (Detached)

$1799999.0

Price drop by 5.3%

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

Nestled In The Heart Of Vibrant Oakwood Village Community, This Stunning Fully Custom Designed and Renovated Home features over 2500 Square Feet Of Li

24 Photos

1046 Dovercourt Road, Toronto, ON , MLS #W12915718 , Image - 1

1.28 km from Winona Drive and St Clair Avenue West

1046 Dovercourt Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12915718

Residential Freehold (Duplex)

$2299988.0

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

Live Smart or Invest Wise Unique Oversized Victorian Duplex in Prime Downtown Location. An exceptional opportunity to own a fully leased, beautifully

40 Photos

84 Old Forest Hill Road, Toronto, ON , MLS #C12923128 , Image - 1

2.39 km from Winona Drive and St Clair Avenue West

84 Old Forest Hill Road Forest Hill South, Toronto, ON MLS® C12923128

Residential Freehold (Detached)

$14880000.0

5 +1 Beds
8 Baths
5000 + sq-ft

Redefining luxury living in Forest Hill, this exceptional estate rests on a 60 ft x 135 ft lot and embodies design excellence by OE Design, where craf

17 Photos

72 Walmer Road, Toronto, ON , MLS #C12406129 , Image - 1

2.34 km from Winona Drive and St Clair Avenue West

72 Walmer Road Annex, Toronto, ON MLS® C12406129

Residential Freehold (Multiplex)

$3595000.0

6 Beds
7 Baths
3500-5000 sq-ft

Annex Grand and Stately Residence. An Impressive Investment Opportunity In The Heart Of The Annex! Fully Detached With 5 Parking Spots And 5 Lockers.

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

24 Photos

1059 Bathurst Street, Toronto, ON , MLS #C12906848 , Image - 1

1.76 km from Winona Drive and St Clair Avenue West

1059 Bathurst Street Annex, Toronto, ON MLS® C12906848

Residential Freehold (Semi-Detached )

$999000.0

3 +1 Beds
1 Baths
700-1100 sq-ft

Welcome to 1059 Bathurst Street: A Rare Find in The Annex! Nestled in the heart of Toronto's dynamic Annex neighbourhood, 1059 Bathurst Street offers

45 Photos

1410 Dupont Street, Toronto, ON , MLS #W12765860 , Image - 1

1.89 km from Winona Drive and St Clair Avenue West

Unit-2708, 1410 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12765860

Residential Condo & Other (Condo Apartment)

$419900.0

1 Beds
1 Baths
0-499 sq-ft

VIEWS FOR DAYS!!! Attention first time home buyers! You will love this condo with a West facing balcony with PANORAMIC views that overlook downtown To

20 Photos

78 Warren Road, Toronto, ON , MLS #C12694490 , Image - 1

2.15 km from Winona Drive and St Clair Avenue West

Unit-107, 78 Warren Road Casa Loma, Toronto, ON MLS® C12694490

Residential Condo & Other (Co-Ownership Apartment)

$299900.0

1 Baths
0-499 sq-ft

Welcome to this bright, fully renovated ground-floor studio in a classic, boutique building just steps to Casa Loma, Forest Hill Village, and the scen

40 Photos

148 Forest Hill Road, Toronto, ON , MLS #C12185911 , Image - 1

2.62 km from Winona Drive and St Clair Avenue West

148 Forest Hill Road Forest Hill South, Toronto, ON MLS® C12185911

Residential Freehold (Detached)

$8495000.0

Price drop by 19.1%

5 Beds
6 Baths
3500-5000 sq-ft

One of the most epic Georgians in the city. Completely and elegantly renovated; seamlessly marrying character and fine contemporary finishes with over

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

40 Photos

725 Dovercourt Road, Toronto, ON , MLS #C12831228 , Image - 1

2.19 km from Winona Drive and St Clair Avenue West

725 Dovercourt Road Palmerston-Little Italy, Toronto, ON MLS® C12831228

Residential Freehold (Other)

$1799900.0

4 Beds
2 Baths
2000-2500 sq-ft

Discover this professionally maintained mixed-use corner gem at Bloor & Dovercourt, offering both stability and growth potential. The property feature

49 Photos

151 Dewbourne Avenue, Toronto, ON , MLS #C12918614 , Image - 1

1.92 km from Winona Drive and St Clair Avenue West

151 Dewbourne Avenue Humewood-Cedarvale, Toronto, ON MLS® C12918614

Residential Freehold (Detached)

$3499000.0

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

An exceptional opportunity in one of Toronto's most sought-after neighborhoods. This stunning three-story residence sets a new standard for modern lux

41 Photos

9 Lynwood Avenue, Toronto, ON , MLS #C12754966 , Image - 1

2.52 km from Winona Drive and St Clair Avenue West

9 Lynwood Avenue Casa Loma, Toronto, ON MLS® C12754966

Residential Freehold (Detached)

$3999000.0

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

Imagine coming home every day to this classic red brick Toronto home w/ phenomenal street presence where timeless design meets modern family living. A

45 Photos

210 Glenayr Road, Toronto, ON , MLS #C12849824 , Image - 1

1.96 km from Winona Drive and St Clair Avenue West

210 Glenayr Road Forest Hill South, Toronto, ON MLS® C12849824

Residential Freehold (Detached)

$8800000.0

6 +1 Beds
7 Baths
5000 + sq-ft

For Sale At Value Dramatically Less Than Replacement Cost. Builders Own! Extraordinary Custom Built Residence - Architecturally Significant. Architect

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

30 Photos

56 Blandford Street, Toronto, ON , MLS #C12912622 , Image - 1

1.14 km from Winona Drive and St Clair Avenue West

56 Blandford Street Oakwood Village, Toronto, ON MLS® C12912622

Residential Freehold (Semi-Detached )

$899999.0

3 Beds
2 Baths
1100-1500 sq-ft

**Convenient location :short walk to newly built subway on Eglinton Ave. **Nicely renovated & very well-kept property ***Suitable for own use or inves

28 Photos

1155 Davenport Road, Toronto, ON , MLS #C12748946 , Image - 1

0.64 km from Winona Drive and St Clair Avenue West

1155 Davenport Road Wychwood, Toronto, ON MLS® C12748946

Residential Freehold (Store W Apartment/Office)

$1099000.0

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

Excellent Income Property producing property located in the popular Wychwood neighbourhood, situated amongst trendy hip restaurant/bar & pizzeria. Thi

23 Photos

295 Old Weston Road, Toronto, ON , MLS #W12911968 , Image - 1

2.57 km from Winona Drive and St Clair Avenue West

295 Old Weston Road Weston-Pellam Park, Toronto, ON MLS® W12911968

Residential Freehold (Semi-Detached )

$636000.0

3 +2 Beds
2 Baths
700-1100 sq-ft

Semi-Detached, 2 Storey Home (1095 Sq'). Located In The Weston-Pellam Park Neighbourhood. Currently Set Up For Multi-Generational Living. Functional

41 Photos

626 Huron Street, Toronto, ON , MLS #C12707992 , Image - 1

2.4 km from Winona Drive and St Clair Avenue West

626 Huron Street Annex, Toronto, ON MLS® C12707992

Residential Freehold (Fourplex)

$2500000.0

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

Investment opportunity for a luxury multiplex in Toronto's Annex -- Steps from Dupont and Spadina Stations, this well maintained 4-unit property conta

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

39 Photos

77 Hatherley Road, Toronto, ON , MLS #W12695104 , Image - 1

1.67 km from Winona Drive and St Clair Avenue West

77 Hatherley Road Caledonia-Fairbank, Toronto, ON MLS® W12695104

Residential Freehold (Detached)

$1229000.0

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

Fully Renovated Detached Home in Toronto. Style Today, Value Tomorrow. This beautifully renovated detached home offers the best of modern city living

7 Photos

415 Symington Avenue, Toronto, ON , MLS #W12908612 , Image - 1

2.04 km from Winona Drive and St Clair Avenue West

415 Symington Avenue Weston-Pellam Park, Toronto, ON MLS® W12908612

Residential Freehold (Semi-Detached )

$1149000.0

4 Beds
2 Baths
1500-2000 sq-ft

Located in the vibrant Junction Triangle, this semi-detached 2 1/4-storey home offers a fantastic opportunity for renovators, investors, or end-users

40 Photos

1038 St Clair Avenue W, Toronto, ON , MLS #C12904866 , Image - 1

0.53 km from Winona Drive and St Clair Avenue West

1038 St Clair Avenue W Oakwood Village, Toronto, ON MLS® C12904866

Residential Freehold (Store W Apartment/Office)

$2999000.0

9 Beds
7 Baths
3500-5000 sq-ft

Amazing Investment Opportunity! 3-Storey Corner Building Featuring Four Commercial Storefronts Plus Four Large Residential Units (2 x Three Bedroom, 2

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)

$2895000.0

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

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

21 Photos

1787 St Clair Avenue W, Toronto, ON , MLS #W12900590 , Image - 1

2.47 km from Winona Drive and St Clair Avenue West

Unit-621, 1787 St Clair Avenue W Weston-Pellam Park, Toronto, ON MLS® W12900590

Residential Condo & Other (Condo Apartment)

$425000.0

1 Beds
1 Baths
500-599 sq-ft

Scout Condos! Well Laid Out 1 Bed, 1 Bath Unit With 501 SqFT & East Facing Balcony. BrightBedroom With Double Closet & Large Window. Wide Plank Lamina

19 Photos

500 Dupont Street, Toronto, ON , MLS #C12815264 , Image - 1

1.54 km from Winona Drive and St Clair Avenue West

Unit-419, 500 Dupont Street Annex, Toronto, ON MLS® C12815264

Residential Condo & Other (Condo Apartment)

$549000.0

Price drop by 4.5%

1 Beds
1 Baths
500-599 sq-ft

Experience elevated boutique living at Oscar Residences. This southwest-facing 1-bedroom plus study suite showcases a highly desirable open-concept la

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Map View

List View

1787 ST. CLAIR Avenue W, Toronto, ON , MLS #W12910682 , Image - 1

1787 ST. CLAIR Avenue W

Weston-Pellam Park, Toronto, ON

$529900.0

707 Eglinton Avenue W, Toronto, ON , MLS #C12747422 , Image - 1

707 Eglinton Avenue W

Forest Hill South, Toronto, ON

$799000.0

1344 Davenport Road, Toronto, ON , MLS #W12632060 , Image - 1

1344 Davenport Road

Corso Italia-Davenport, Toronto, ON

$688888.0

49 Osler Street, Toronto, ON , MLS #W12917670 , Image - 1

49 Osler Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1089000.0

3 Silverwood Avenue, Toronto, ON , MLS #C12586536 , Image - 1

3 Silverwood Avenue

Forest Hill South, Toronto, ON

$3880000.0

1 Burton Road, Toronto, ON , MLS #C12927954 , Image - 1

1 Burton Road

Forest Hill South, Toronto, ON

$5395000.0

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

34 Mc Farland Avenue

Corso Italia-Davenport, Toronto, ON

$849000.0

342 Spadina Road, Toronto, ON , MLS #C12655918 , Image - 1

342 Spadina Road

Forest Hill South, Toronto, ON

$3075000.0

388 Oakwood Avenue, Toronto, ON , MLS #C12357463 , Image - 1

388 Oakwood Avenue

Oakwood Village, Toronto, ON

$1799999.0

1046 Dovercourt Road, Toronto, ON , MLS #W12915718 , Image - 1

1046 Dovercourt Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$2299988.0

84 Old Forest Hill Road, Toronto, ON , MLS #C12923128 , Image - 1

84 Old Forest Hill Road

Forest Hill South, Toronto, ON

$14880000.0

72 Walmer Road, Toronto, ON , MLS #C12406129 , Image - 1

72 Walmer Road

Annex, Toronto, ON

$3595000.0

1059 Bathurst Street, Toronto, ON , MLS #C12906848 , Image - 1

1059 Bathurst Street

Annex, Toronto, ON

$999000.0

1410 Dupont Street, Toronto, ON , MLS #W12765860 , Image - 1

1410 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$419900.0

78 Warren Road, Toronto, ON , MLS #C12694490 , Image - 1

78 Warren Road

Casa Loma, Toronto, ON

$299900.0

148 Forest Hill Road, Toronto, ON , MLS #C12185911 , Image - 1

148 Forest Hill Road

Forest Hill South, Toronto, ON

$8495000.0

725 Dovercourt Road, Toronto, ON , MLS #C12831228 , Image - 1

725 Dovercourt Road

Palmerston-Little Italy, Toronto, ON

$1799900.0

151 Dewbourne Avenue, Toronto, ON , MLS #C12918614 , Image - 1

151 Dewbourne Avenue

Humewood-Cedarvale, Toronto, ON

$3499000.0

9 Lynwood Avenue, Toronto, ON , MLS #C12754966 , Image - 1

9 Lynwood Avenue

Casa Loma, Toronto, ON

$3999000.0

210 Glenayr Road, Toronto, ON , MLS #C12849824 , Image - 1

210 Glenayr Road

Forest Hill South, Toronto, ON

$8800000.0

56 Blandford Street, Toronto, ON , MLS #C12912622 , Image - 1

56 Blandford Street

Oakwood Village, Toronto, ON

$899999.0

1155 Davenport Road, Toronto, ON , MLS #C12748946 , Image - 1

1155 Davenport Road

Wychwood, Toronto, ON

$1099000.0

295 Old Weston Road, Toronto, ON , MLS #W12911968 , Image - 1

295 Old Weston Road

Weston-Pellam Park, Toronto, ON

$636000.0

626 Huron Street, Toronto, ON , MLS #C12707992 , Image - 1

626 Huron Street

Annex, Toronto, ON

$2500000.0

77 Hatherley Road, Toronto, ON , MLS #W12695104 , Image - 1

77 Hatherley Road

Caledonia-Fairbank, Toronto, ON

$1229000.0

415 Symington Avenue, Toronto, ON , MLS #W12908612 , Image - 1

415 Symington Avenue

Weston-Pellam Park, Toronto, ON

$1149000.0

1038 St Clair Avenue W, Toronto, ON , MLS #C12904866 , Image - 1

1038 St Clair Avenue W

Oakwood Village, Toronto, ON

$2999000.0

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

113 Dupont Street

Annex, Toronto, ON

$2895000.0

1787 St Clair Avenue W, Toronto, ON , MLS #W12900590 , Image - 1

1787 St Clair Avenue W

Weston-Pellam Park, Toronto, ON

$425000.0

500 Dupont Street, Toronto, ON , MLS #C12815264 , Image - 1

500 Dupont Street

Annex, Toronto, ON

$549000.0

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