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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: February 13, 2026

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

Open House : Sat Feb 14, 11:00 AM to 01:00 PM

24 Photos

65 Turntable Crescent, Toronto, ON , MLS #W12739064 , Image - 1

1.75 km from Winona Drive and St Clair Avenue West

Unit-90, 65 Turntable Crescent Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12739064

Residential Condo & Other (Condo Townhouse)

$674900.0

Price drop by 0.7%

3 Beds
2 Baths
1000-1199 sq-ft

Welcome to 65 Turntable Crescent, Unit 90 - a freshly renovated and professionally painted 3-bedroom, 2-bathroom stacked townhouse, now priced at $679

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

33 Photos

499 Palmerston Boulevard, Toronto, ON , MLS #C12685454 , Image - 1

2.52 km from Winona Drive and St Clair Avenue West

499 Palmerston Boulevard Palmerston-Little Italy, Toronto, ON MLS® C12685454

Residential Freehold (Semi-Detached )

$2550000.0

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

Grand Edwardian 3-storey residence with private drive on a superb 29' x 138' lot. Presently 3-self contained suites, all with individual heating & sep

24 Photos

1059 Bathurst Street, Toronto, ON , MLS #C12775950 , Image - 1

1.76 km from Winona Drive and St Clair Avenue West

1059 Bathurst Street Annex, Toronto, ON MLS® C12775950

Residential Freehold (Semi-Detached )

$1150000.0

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

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

46 Photos

62 Hounslow Heath Road, Toronto, ON , MLS #W12774710 , Image - 1

2.3 km from Winona Drive and St Clair Avenue West

62 Hounslow Heath Road Weston-Pellam Park, Toronto, ON MLS® W12774710

Residential Freehold (Semi-Detached )

$1090000.0

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

Spacious & Versatile Semi Detached in Weston Pellam Park. Perfect for Multigenerational Living. Discover the ideal balance of connection and independe

43 Photos

1001 Roselawn Avenue, Toronto, ON , MLS #W12697934 , Image - 1

2.56 km from Winona Drive and St Clair Avenue West

Unit-205, 1001 Roselawn Avenue Briar Hill-Belgravia, Toronto, ON MLS® W12697934

Residential Condo & Other (Condo Apartment)

$799900.0

2 +1 Beds
2 Baths
900-999 sq-ft

Welcome To 'Forest Hill Lofts', An Art Deco Masterpiece *Bright South Facing Loft With Beautiful Serene Views Of Walter Saunders Park & The York Beltl

49 Photos

290 Russell Hill Road, Toronto, ON , MLS #C12756928 , Image - 1

2.03 km from Winona Drive and St Clair Avenue West

290 Russell Hill Road Casa Loma, Toronto, ON MLS® C12756928

Residential Freehold (Detached)

$6095000.0

6 +1 Beds
7 Baths
5000 + sq-ft

Situated in one of Toronto's most sought-after neighbourhoods, this custom-built, three-story home offers over 6,700 sqft of luxurious living space th

25 Photos

185 Alberta Avenue, Toronto, ON , MLS #C12768918 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-205, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C12768918

Residential Condo & Other (Common Element Condo)

$939000.0

2 Beds
2 Baths
700-799 sq-ft

Rare Opportunity To Own The Only Unit In The Building Featuring A Massive 442 Sq. Ft. Private Terrace With Gas BBQ Line And Sweeping City Views. Inclu

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

5 Photos

205 Heath Street W, Toronto, ON , MLS #C12642522 , Image - 1

1.85 km from Winona Drive and St Clair Avenue West

205 Heath Street W Casa Loma, Toronto, ON MLS® C12642522

Residential Freehold (Detached)

$5990000.0

4 Beds
3 Baths
5000 + sq-ft

Builder's dream Lot! 72x152' South facing lot located in One of the City's most affluent & sought after Neighbourhoods. Permits and plans fully approv

37 Photos

420 Harvie Avenue, Toronto, ON , MLS #W12767804 , Image - 1

2.02 km from Winona Drive and St Clair Avenue West

420 Harvie Avenue Caledonia-Fairbank, Toronto, ON MLS® W12767804

Residential Freehold (Detached)

$1409000.0

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

Fantastic Detached Family Home in a Caledonia-Fairbank Neighborhood! This truly custom-built home features an open-concept main floor designed for ent

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

19 Photos

185 Alberta Avenue, Toronto, ON , MLS #C12682722 , Image - 1

0.09 km from Winona Drive and St Clair Avenue West

Unit-1103, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C12682722

Residential Condo & Other (Condo Apartment)

$704900.0

Price drop by 3.4%

2 Beds
2 Baths
800-899 sq-ft

Bright - Spacious - Vacant - 2 bedrooms, 2 bathrooms, east facing balcony with unobstructed views. Builder's Floor Plan attached. Floor to ceiling win

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

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

33 Photos

6 Parkwood Avenue, Toronto, ON , MLS #C12670742 , Image - 1

1.9 km from Winona Drive and St Clair Avenue West

Unit-TH107, 6 Parkwood Avenue Casa Loma, Toronto, ON MLS® C12670742

Residential Condo & Other (Condo Apartment)

$1398000.0

2 +1 Beds
3 Baths
1200-1399 sq-ft

Welcome To This Exceptional 2-storey Townhouse At The Code Condos, Located In The Heart Of Prestigious Forest Hill South Neighbourhood, An Exclusive L

25 Photos

2020 Bathurst Street, Toronto, ON , MLS #C12616922 , Image - 1

2.35 km from Winona Drive and St Clair Avenue West

Unit-331, 2020 Bathurst Street Humewood-Cedarvale, Toronto, ON MLS® C12616922

Residential Condo & Other (Condo Apartment)

$429000.0

Price drop by 16.7%

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

This stunning 1-bed plus den, 1-bath condo in the new Forest Hill Condominiums by Centre court Developments offers top-of-the-line luxury finishes and

49 Photos

151 Dewbourne Avenue, Toronto, ON , MLS #C12756136 , Image - 1

1.92 km from Winona Drive and St Clair Avenue West

151 Dewbourne Avenue Humewood-Cedarvale, Toronto, ON MLS® C12756136

Residential Freehold (Detached)

$3333000.0

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

A rare opportunity to own a stunning 3-storey residence redefining luxury living. This meticulously designed 4,600+ sq ft family estate features a pri

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

134 Tyrrel Avenue, Toronto, ON , MLS #C12756856 , Image - 1

0.49 km from Winona Drive and St Clair Avenue West

134 Tyrrel Avenue Wychwood, Toronto, ON MLS® C12756856

Residential Freehold (Detached)

$2525000.0

3 Beds
2 Baths
1500-2000 sq-ft

Opportunity awaits in the vibrant Wychwood-Hillcrest neighbourhood! This rare mixed-use corner property has been fully renovated back to the studs and

32 Photos

11 Foundry Avenue, Toronto, ON , MLS #W12756468 , Image - 1

1.77 km from Winona Drive and St Clair Avenue West

Unit-229, 11 Foundry Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12756468

Residential Condo & Other (Condo Townhouse)

$939900.0

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

Experience modern urban living in this beautifully upgraded, upper-level corner townhome in vibrant Davenport Village. This bright, 3-storey condo tow

14 Photos

327 Vaughan Road, Toronto, ON , MLS #C12690398 , Image - 1

1.0 km from Winona Drive and St Clair Avenue West

327 Vaughan Road Humewood-Cedarvale, Toronto, ON MLS® C12690398

Residential Freehold (Triplex)

$899900.0

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

Client RemarksRare opportunity to own a purpose-built triplex in the highly sought-after Humewood-Cedarvale neighbourhood! This turnkey, income-genera

44 Photos

385 Osler Street, Toronto, ON , MLS #W12750168 , Image - 1

2.4 km from Winona Drive and St Clair Avenue West

Unit-202, 385 Osler Street Weston-Pellam Park, Toronto, ON MLS® W12750168

Residential Condo & Other (Condo Apartment)

$599000.0

2 Beds
2 Baths
700-799 sq-ft

Extra, Extra-Read All About It! Searching for the perfect unit with all the right features and the right price? We've got The Scoop-Welcome to Unit 20

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

45 Photos

498 Roxton Road, Toronto, ON , MLS #C12747068 , Image - 1

2.27 km from Winona Drive and St Clair Avenue West

498 Roxton Road Palmerston-Little Italy, Toronto, ON MLS® C12747068

Residential Freehold (Detached)

$3850000.0

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

Toronto's take on a New York-inspired industrial soft loft. A rare detached family home offering nearly 4,500 sq ft of living space across four levels

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

30 Photos

176 Symington Avenue, Toronto, ON , MLS #W12743038 , Image - 1

2.48 km from Winona Drive and St Clair Avenue West

176 Symington Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12743038

Residential Freehold (Semi-Detached )

$1199999.0

3 Beds
3 Baths
1100-1500 sq-ft

Solid investment on Symington. Spacious 3 bedroom/ 3 bathroom income producing duplex located in the delightful and vibrant Wallace- Emerson neighbour

26 Photos

2098 Dufferin Street, Toronto, ON , MLS #W12451412 , Image - 1

1.47 km from Winona Drive and St Clair Avenue West

2098 Dufferin Street Caledonia-Fairbank, Toronto, ON MLS® W12451412

Residential Freehold (Detached)

$899900.0

Price drop by 5.2%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to 2098 Dufferin Street! This beautifully maintained two-storey detached home offers timeless charm and awaits your personal touch. The sun-dr

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

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

33 Photos

21 Thornton Avenue, Toronto, ON , MLS #W12735166 , Image - 1

2.35 km from Winona Drive and St Clair Avenue West

21 Thornton Avenue Caledonia-Fairbank, Toronto, ON MLS® W12735166

Residential Freehold (Detached)

$1399900.0

4 +2 Beds
4 Baths
2000-2500 sq-ft

This fabulous custom home was rebuilt in 2017 and boasts over 3,000 square feet of quality living space. The entrance features custom stamped concrete

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

21 Photos

2433 Dufferin Street, Toronto, ON , MLS #W12715024 , Image - 1

2.56 km from Winona Drive and St Clair Avenue West

Unit-811, 2433 Dufferin Street Briar Hill-Belgravia, Toronto, ON MLS® W12715024

Residential Condo & Other (Condo Apartment)

$699990.0

3 +1 Beds
2 Baths
1200-1399 sq-ft

Attention First Time Buyers!!!! Brand New Condo - HST Rebate Applicable. Builder Forms will be prepared by listing agent Welcome to 8 Haus Condos - ov

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

19 Photos

816 Lansdowne Avenue, Toronto, ON , MLS #W12663834 , Image - 1

2.04 km from Winona Drive and St Clair Avenue West

Unit-1015, 816 Lansdowne Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12663834

Residential Condo & Other (Condo Apartment)

$580000.0

1 Beds
1 Baths
500-599 sq-ft

Great amenities and location! TTC At Your Door Step. 8 Min Walk To Subway Station. GO Train Or Up Express. Bright and spacious one bedroom featuring a

17 Photos

235 St Clair Avenue W, Toronto, ON , MLS #C12703442 , Image - 1

2.27 km from Winona Drive and St Clair Avenue West

Unit-301, 235 St Clair Avenue W Casa Loma, Toronto, ON MLS® C12703442

Residential Condo & Other (Condo Apartment)

$1130000.0

2 Beds
2 Baths
1000-1199 sq-ft

Discover An Exceptional Opportunity To Own A Meticulously Renovated 2-Bedroom, 2-Bathroom Suite In One Of Midtown Toronto's Most Desirable Boutique Ad

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Map View

List View

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

9 Lynwood Avenue

Casa Loma, Toronto, ON

$3999000.0

65 Turntable Crescent, Toronto, ON , MLS #W12739064 , Image - 1

65 Turntable Crescent

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$674900.0

499 Palmerston Boulevard, Toronto, ON , MLS #C12685454 , Image - 1

499 Palmerston Boulevard

Palmerston-Little Italy, Toronto, ON

$2550000.0

1059 Bathurst Street, Toronto, ON , MLS #C12775950 , Image - 1

1059 Bathurst Street

Annex, Toronto, ON

$1150000.0

62 Hounslow Heath Road, Toronto, ON , MLS #W12774710 , Image - 1

62 Hounslow Heath Road

Weston-Pellam Park, Toronto, ON

$1090000.0

1001 Roselawn Avenue, Toronto, ON , MLS #W12697934 , Image - 1

1001 Roselawn Avenue

Briar Hill-Belgravia, Toronto, ON

$799900.0

290 Russell Hill Road, Toronto, ON , MLS #C12756928 , Image - 1

290 Russell Hill Road

Casa Loma, Toronto, ON

$6095000.0

185 Alberta Avenue, Toronto, ON , MLS #C12768918 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$939000.0

205 Heath Street W, Toronto, ON , MLS #C12642522 , Image - 1

205 Heath Street W

Casa Loma, Toronto, ON

$5990000.0

420 Harvie Avenue, Toronto, ON , MLS #W12767804 , Image - 1

420 Harvie Avenue

Caledonia-Fairbank, Toronto, ON

$1409000.0

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

1410 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$419900.0

185 Alberta Avenue, Toronto, ON , MLS #C12682722 , Image - 1

185 Alberta Avenue

Oakwood Village, Toronto, ON

$704900.0

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

342 Spadina Road

Forest Hill South, Toronto, ON

$3075000.0

6 Parkwood Avenue, Toronto, ON , MLS #C12670742 , Image - 1

6 Parkwood Avenue

Casa Loma, Toronto, ON

$1398000.0

2020 Bathurst Street, Toronto, ON , MLS #C12616922 , Image - 1

2020 Bathurst Street

Humewood-Cedarvale, Toronto, ON

$429000.0

151 Dewbourne Avenue, Toronto, ON , MLS #C12756136 , Image - 1

151 Dewbourne Avenue

Humewood-Cedarvale, Toronto, ON

$3333000.0

134 Tyrrel Avenue, Toronto, ON , MLS #C12756856 , Image - 1

134 Tyrrel Avenue

Wychwood, Toronto, ON

$2525000.0

11 Foundry Avenue, Toronto, ON , MLS #W12756468 , Image - 1

11 Foundry Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$939900.0

327 Vaughan Road, Toronto, ON , MLS #C12690398 , Image - 1

327 Vaughan Road

Humewood-Cedarvale, Toronto, ON

$899900.0

385 Osler Street, Toronto, ON , MLS #W12750168 , Image - 1

385 Osler Street

Weston-Pellam Park, Toronto, ON

$599000.0

498 Roxton Road, Toronto, ON , MLS #C12747068 , Image - 1

498 Roxton Road

Palmerston-Little Italy, Toronto, ON

$3850000.0

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

707 Eglinton Avenue W

Forest Hill South, Toronto, ON

$799000.0

176 Symington Avenue, Toronto, ON , MLS #W12743038 , Image - 1

176 Symington Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1199999.0

2098 Dufferin Street, Toronto, ON , MLS #W12451412 , Image - 1

2098 Dufferin Street

Caledonia-Fairbank, Toronto, ON

$899900.0

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

388 Oakwood Avenue

Oakwood Village, Toronto, ON

$1799999.0

21 Thornton Avenue, Toronto, ON , MLS #W12735166 , Image - 1

21 Thornton Avenue

Caledonia-Fairbank, Toronto, ON

$1399900.0

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

77 Hatherley Road

Caledonia-Fairbank, Toronto, ON

$1229000.0

2433 Dufferin Street, Toronto, ON , MLS #W12715024 , Image - 1

2433 Dufferin Street

Briar Hill-Belgravia, Toronto, ON

$699990.0

816 Lansdowne Avenue, Toronto, ON , MLS #W12663834 , Image - 1

816 Lansdowne Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$580000.0

235 St Clair Avenue W, Toronto, ON , MLS #C12703442 , Image - 1

235 St Clair Avenue W

Casa Loma, Toronto, ON

$1130000.0

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