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House for Sale near Davenport Road and Winona Drive, C02

Showing results 1 - 30 of 30

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

Last Updated: November 12, 2026

50 Photos

729 Gladstone Avenue, Toronto, ON , MLS #W14155838 , Image - 1

1.14 km from Davenport Road and Winona Drive

729 Gladstone Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14155838

Residential Freehold (Detached)

$2299900.0

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

You've walked past it. You've slowed down. You've said, Okay, I love that house! Now's your chance to see what's behind the white facade. If you're lo

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

38 Photos

500 Dupont Street, Toronto, ON , MLS #C13735252 , Image - 1

1.16 km from Davenport Road and Winona Drive

Unit-717, 500 Dupont Street Annex, Toronto, ON MLS® C13735252

Residential Condo & Other (Condo Apartment)

$649900.0

2 Beds
1 Baths
600-699 sq-ft

*Power of Sale* 2 Bedroom, 2 Bathroom Condo For Sale In The New Oscar Residences. This Unit Features A Functional Layout Including Open Concept Kitche

50 Photos

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

0.38 km from Davenport Road and Winona Drive

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

1 Photos

0.11 km from Davenport Road and Winona Drive

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

Pre-Construction

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

0.3 km from Davenport Road and Winona Drive

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

0.33 km from Davenport Road and Winona Drive

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

19 Photos

39 Pendrith Street, Toronto, ON , MLS #W13826536 , Image - 1

1.1 km from Davenport Road and Winona Drive

39 Pendrith Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13826536

Residential Freehold (Semi-Detached )

$1379000.0

Price drop by 4.9%

3 Beds
3 Baths
1100-1500 sq-ft

An Exceptional Opportunity In The Heart Of Christie Pits! This Versatile 2-Storey Semi Offers A Rare Combination Of Location, Lifestyle And Income Pot

50 Photos

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

1.04 km from Davenport Road and Winona Drive

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

Pre-Construction

Arbor West

10024 Mississauga Road, Brampton

From $559,990

Project Info

88 Buildings
204 Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Caivan

46 Photos

1307 Dufferin Street, Toronto, ON , MLS #W14169326 , Image - 1

1.01 km from Davenport Road and Winona Drive

1307 Dufferin Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14169326

Residential Freehold (Semi-Detached )

$1048000.0

5 +2 Beds
3 Baths
1100-1500 sq-ft

Welcome to 1307 Dufferin St! Freshly updated with income potential, Offered with vacant possession! Larger than it appears w/ 1381sf above ground (MPA

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

31 Photos

1185 Dupont Street, Toronto, ON , MLS #W14168478 , Image - 1

1.06 km from Davenport Road and Winona Drive

Unit-1709, 1185 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14168478

Residential Condo & Other (Condo Apartment)

$899900.0

2 Beds
2 Baths
700-799 sq-ft

An opportunity to own at Galleria on the Park without paying current developer pricing for comparable inventory! Situated on the 17th floor, this cont

45 Photos

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

0.67 km from Davenport Road and Winona Drive

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

0.06 km from Davenport Road and Winona Drive

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

Pre-Construction

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

14 Photos

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

0.51 km from Davenport Road and Winona Drive

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

42 Photos

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

1.11 km from Davenport Road and Winona Drive

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

0.49 km from Davenport Road and Winona Drive

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

32 Photos

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

0.49 km from Davenport Road and Winona Drive

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

Pre-Construction

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

43 Photos

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

0.55 km from Davenport Road and Winona Drive

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

0.35 km from Davenport Road and Winona Drive

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

30 Photos

837 Gladstone Avenue, Toronto, ON , MLS #W13844918 , Image - 1

0.93 km from Davenport Road and Winona Drive

837 Gladstone Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13844918

Residential Freehold (Duplex)

$1559000.0

Price drop by 0.6%

5 Beds
3 Baths
2000-2500 sq-ft

Welcome to 837 Gladstone Avenue - a rare opportunity in one of Toronto's fastest-growing neighbourhoods. Nestled on a quiet street in the heart of Wal

20 Photos

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

0.47 km from Davenport Road and Winona Drive

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

Pre-Construction

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

33 Photos

987 Ossington Avenue, Toronto, ON , MLS #W14162294 , Image - 1

0.72 km from Davenport Road and Winona Drive

987 Ossington Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14162294

Residential Freehold (Semi-Detached )

$899000.0

3 Beds
2 Baths
1100-1500 sq-ft

An exceptional opportunity to create your dream home in the heart of Dovercourt Village. Offered for the first time in over 60 years, this Large, Bric

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

50 Photos

98 Beaver Terrace, Toronto, ON , MLS #W13776648 , Image - 1

1.17 km from Davenport Road and Winona Drive

98 Beaver Terrace Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13776648

Residential Freehold (Semi-Detached )

$1249000.0

Price drop by 6.7%

3 Beds
2 Baths
1100-1500 sq-ft

Rare Toronto cul-de-sac gem! This clean, meticulously maintained property stands completely apart from its neighbors, boasting four exclusive advantag

11 Photos

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

0.51 km from Davenport Road and Winona Drive

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

42 Photos

127 Salem Avenue, Toronto, ON , MLS #W13822392 , Image - 1

1.19 km from Davenport Road and Winona Drive

127 Salem Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W13822392

Residential Freehold (Semi-Detached )

$729000.0

3 Beds
2 Baths
700-1100 sq-ft

Fantastic opportunity in the heart of Bloorcourt Village! This 3-bedroom semi offers the comfort and flexibility of a house without condo fees, plus t

Pre-Construction

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

27 Photos

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

0.69 km from Davenport Road and Winona Drive

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

27 Photos

2B Alcina Avenue, Toronto, ON , MLS #C14143962 , Image - 1

1.2 km from Davenport Road and Winona Drive

2B Alcina Avenue Wychwood, Toronto, ON MLS® C14143962

Residential Freehold (Att/Row/Townhouse)

$1199000.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome to 2B Alcina Ave, a rare freehold townhouse situated in Wychwood. Nestled in the highly coveted Hillcrest School district, steps from the Wych

33 Photos

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

0.49 km from Davenport Road and Winona Drive

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

17 Photos

800 Davenport Road, Toronto, ON , MLS #C14154772 , Image - 1

0.99 km from Davenport Road and Winona Drive

800 Davenport Road Wychwood, Toronto, ON MLS® C14154772

Residential Freehold (Detached)

$1125000.0

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

Prime Location in Vibrant Wychwood! This renovated home offers an exceptional opportunity for homeowners and investors alike! Featuring a spacious mai

Pre-Construction

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

1 Photos

1.19 km from Davenport Road and Winona Drive

865 Dovercourt Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14154900

Residential Freehold (Semi-Detached )

$850000.0

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

Fantastic residential and investment opportunity located at 865 Dovercourt Road, offering versatile all-residential use with strong income potential o

25 Photos

179 Yarmouth Road, Toronto, ON , MLS #W14125252 , Image - 1

0.72 km from Davenport Road and Winona Drive

179 Yarmouth Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W14125252

Residential Freehold (Detached)

$1385000.0

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

Renovated by a designer for her own family, 179 Yarmouth Road is a home where every square foot has a purpose. The open-concept main floor is filled w

Shortlisted Properties

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729 Gladstone Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$2299900.0

500 Dupont Street

Annex, Toronto, ON

$649900.0

35 Regal Road

Corso Italia-Davenport, Toronto, ON

$1749988.0

1204 Ossington Avenue

Wychwood, Toronto, ON

$408000.0

43 Marchmount Road

Wychwood, Toronto, ON

$1288000.0

409 Melita Crescent

Wychwood, Toronto, ON

$949000.0

39 Pendrith Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1379000.0

185 Glenholme Avenue

Oakwood Village, Toronto, ON

$1899000.0

1307 Dufferin Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1048000.0

1185 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$899900.0

402 Salem Avenue N

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$4999000.0

132 Marchmount Road

Wychwood, Toronto, ON

$1285000.0

60 Greensides Avenue

Wychwood, Toronto, ON

$1050000.0

44 Conway Avenue

Oakwood Village, Toronto, ON

$919000.0

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$870796.0

858 DuPont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$901770.0

1045 Ossington Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$999900.0

55 Oakwood Avenue

Wychwood, Toronto, ON

$1225000.0

837 Gladstone Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1559000.0

248 Benson Avenue

Wychwood, Toronto, ON

$1149900.0

987 Ossington Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$899000.0

98 Beaver Terrace

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1249000.0

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$539000.0

127 Salem Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$729000.0

185 Alberta Avenue

Oakwood Village, Toronto, ON

$568000.0

2B Alcina Avenue

Wychwood, Toronto, ON

$1199000.0

858 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$769000.0

800 Davenport Road

Wychwood, Toronto, ON

$1125000.0

865 Dovercourt Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$850000.0

179 Yarmouth Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1385000.0

House for Sale near Davenport Road and Winona Drive, C02

1515 Pickering Parkway

Arbor West

Corktown Plaza

Lily at Crosstown

The Clove Condos

The Laurels

The Rebecca Condos

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