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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: December 05, 2025

33 Photos

499 Palmerston Boulevard, Toronto, ON , MLS #C12352193 , Image - 1

1.95 km from Davenport Road and Winona Drive

499 Palmerston Boulevard Palmerston-Little Italy, Toronto, ON MLS® C12352193

Residential Freehold (Triplex)

$2674999.0

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

Substantial Home in the Heart of the Annex. On iconic Palmerston Boulevard, this spacious and legal triplex combines character, flexibility, and prime

49 Photos

380 Macpherson Avenue, Toronto, ON , MLS #C12480510 , Image - 1

1.98 km from Davenport Road and Winona Drive

Unit-333, 380 Macpherson Avenue Casa Loma, Toronto, ON MLS® C12480510

Residential Condo & Other (Condo Apartment)

$459000.0

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

PRICED TO SELL! Popular Madison Avenue Lofts, Art Deco styling, exposed concrete, chic New York inspired loft with 14' ceilings! Coveted 1 Bedroom +

19 Photos

1420 Dupont Street, Toronto, ON , MLS #W12599470 , Image - 1

1.7 km from Davenport Road and Winona Drive

Unit-1407, 1420 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12599470

Residential Condo & Other (Condo Apartment)

$449000.0

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

Offers anytime! The price of a 1-bed but with a den + parking, win-win. This 1+den feels like the perfect mix of calm comfort and city energy, just th

32 Photos

1113 Dufferin Street, Toronto, ON , MLS #W12494846 , Image - 1

1.42 km from Davenport Road and Winona Drive

1113 Dufferin Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12494846

Residential Freehold (Detached)

$1090000.0

Price drop by 19.1%

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

Welcome to this spacious, move-in-ready detached 6-bedroom home, ideally located in one of Toronto's most vibrant and central neighbourhoods. Perfect

Pre-Construction

Rosehaven Ivy Rouge

Burnhamthorpe Road West & Sixth Line, Oakville

From $1,099,990 to $2,079,990

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes

46 Photos

215 Lonsmount Drive, Toronto, ON , MLS #C12375188 , Image - 1

1.75 km from Davenport Road and Winona Drive

215 Lonsmount Drive Forest Hill South, Toronto, ON MLS® C12375188

Residential Freehold (Detached)

$5380000.0

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

Contemporary Residence Nestled On A Private Lush Ravine Setting. Spectacular Residence Which Redefines Modern Living. Every Detail Crafted For Comfort

40 Photos

17 Ardwold Gate, Toronto, ON , MLS #C12377052 , Image - 1

1.94 km from Davenport Road and Winona Drive

17 Ardwold Gate Casa Loma, Toronto, ON MLS® C12377052

Residential Freehold (Detached)

$34500000.0

6 +2 Beds
11 Baths
5000 + sq-ft

Discover One Of The Most Architecturally Significant And Breathtaking Estates In Toronto, Discretely Nestled At The End Of A Cul-De-Sac And Perched Ab

34 Photos

1083 Dupont Street, Toronto, ON , MLS #W12226265 , Image - 1

0.79 km from Davenport Road and Winona Drive

1083 Dupont Street Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12226265

Residential Freehold (Detached)

$1628600.0

Price drop by 3.0%

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

Welcome to 1083 Dupont Street A Rare Opportunity in a Rapidly Growing Toronto West Corridor! This charming and well-maintained home is perfect for la

32 Photos

11 Foundry Avenue, Toronto, ON , MLS #W12595480 , Image - 1

1.57 km from Davenport Road and Winona Drive

Unit-229, 11 Foundry Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12595480

Residential Condo & Other (Condo Townhouse)

$940000.0

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

This upgraded upper-level, corner townhome in vibrant Davenport Village offers west-facing park views and unforgettable sunset skies from both a priva

Pre-Construction

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard

From $879,990 - $1,339,990

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes

50 Photos

447 Walmer Road, Toronto, ON , MLS #C12439875 , Image - 1

1.89 km from Davenport Road and Winona Drive

Unit-608, 447 Walmer Road Forest Hill South, Toronto, ON MLS® C12439875

Residential Condo & Other (Condo Apartment)

$1899900.0

Price drop by 5.0%

2 +1 Beds
3 Baths
2000-2249 sq-ft

Exquisite Corner Suite with Complete Renovation!Welcome to a stunning showcase of luxury and sophistication in this meticulously renovated 2-bedroom +

47 Photos

157 Glenholme Avenue, Toronto, ON , MLS #C12543730 , Image - 1

0.94 km from Davenport Road and Winona Drive

157 Glenholme Avenue Oakwood Village, Toronto, ON MLS® C12543730

Residential Freehold (Detached)

$1549900.0

5 +2 Beds
5 Baths
2000-2500 sq-ft

Welcome to St. Clair Village's perfect family home with 5 bedrooms & 5 Washrooms& Basement apartment. Over half year thoroughly renovated from Top to

38 Photos

253 Albany Avenue, Toronto, ON , MLS #C12551578 , Image - 1

1.41 km from Davenport Road and Winona Drive

253 Albany Avenue Annex, Toronto, ON MLS® C12551578

Residential Freehold (Detached)

$2095000.0

4 Beds
4 Baths
2000-2500 sq-ft

Welcome To 253 Albany Ave. In A Neighbourhood Known For Its Charming But Narrow Lots, This Rare Annex Gem Stretches Nearly 30 Feet Wide Offering Expan

40 Photos

351 Clinton Street, Toronto, ON , MLS #C12386911 , Image - 1

1.68 km from Davenport Road and Winona Drive

351 Clinton Street Palmerston-Little Italy, Toronto, ON MLS® C12386911

Residential Freehold (Triplex)

$2248800.0

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

A Rare Opportunity To Own A Legal Triplex In The Heart Of Palmerston-Little Italy, Steps Away For Christie Park, Christy Subway Station, Vibrant Bloor

Pre-Construction

Angus Glen South Village

4134 16th Avenue, Markham

From From $2,130,000 to $5,820,000

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Kylemore Communities

43 Photos

52 Nina Street, Toronto, ON , MLS #C12406032 , Image - 1

1.34 km from Davenport Road and Winona Drive

52 Nina Street Casa Loma, Toronto, ON MLS® C12406032

Residential Freehold (Detached)

$2198000.0

Price drop by 15.4%

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

Nestled in the sought-after Casa Loma enclave, this charming 3+1 bedroom, 3 bathroom home blends timeless elegance with modern comfort. Located steps

37 Photos

40 Westmoreland Avenue, Toronto, ON , MLS #W12465535 , Image - 1

1.44 km from Davenport Road and Winona Drive

Unit-TH7, 40 Westmoreland Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12465535

Residential Condo & Other (Condo Townhouse)

$1748000.0

Price drop by 2.8%

2 +1 Beds
3 Baths
1800-1999 sq-ft

Magnificent 4 storey Townhome carved from a 1914 Neo-Gothic Church, creating one of Toronto's most spectacular landmark Church conversions. Meticulous

41 Photos

185 Alberta Avenue, Toronto, ON , MLS #C12473819 , Image - 1

0.69 km from Davenport Road and Winona Drive

Unit-807, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C12473819

Residential Condo & Other (Condo Apartment)

$1295000.0

3 Beds
2 Baths
1200-1399 sq-ft

**Price Reduced by $100k !! Now is your opportunity to own this brand new unit before its gone** Welcome To The Striking St. Clair Village Boutique Co

26 Photos

185 Alberta Avenue, Toronto, ON , MLS #C12473820 , Image - 1

0.69 km from Davenport Road and Winona Drive

Unit-1001, 185 Alberta Avenue Oakwood Village, Toronto, ON MLS® C12473820

Residential Condo & Other (Condo Apartment)

$1095000.0

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

**Price Reduced by $100k !! Now is your opportunity to own this brand new unit before its gone** Welcome To The Striking St. Clair Village Boutique Co

Pre-Construction

The Platform at Station Park

35 Wellington St S, Kitchener

From $524,900 to $779900

Project Info

Units
Condos

Property Mix

Floorplans coming soon

Developer:VanMar Developments

28 Photos

1943 Dufferin Street, Toronto, ON , MLS #W12388062 , Image - 1

1.56 km from Davenport Road and Winona Drive

1943 Dufferin Street Corso Italia-Davenport, Toronto, ON MLS® W12388062

Residential Freehold (Duplex)

$899000.0

Price drop by 3.3%

3 +1 Beds
4 Baths
< 700 sq-ft

Updated Semi in Desirable Corso Italia-Davenport neighborhood !!. Welcoming front porch. Main Fl offer Living, Formal Dining (can be use as Den/Office

50 Photos

497 Brunswick Avenue, Toronto, ON , MLS #C12421386 , Image - 1

1.66 km from Davenport Road and Winona Drive

497 Brunswick Avenue Annex, Toronto, ON MLS® C12421386

Residential Freehold (Semi-Detached )

$3495000.0

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

A True Designer's Paradise, This 3+1 Bedroom, 5 Bathroom Restored Victorian Home Is Truly A Sight To Behold! With No Detail Spared, This 3 Storey Home

23 Photos

70 Montclair Avenue W, Toronto, ON , MLS #C12339798 , Image - 1

1.95 km from Davenport Road and Winona Drive

Unit-203, 70 Montclair Avenue W Forest Hill South, Toronto, ON MLS® C12339798

Residential Condo & Other (Condo Apartment)

$1248000.0

3 +1 Beds
2 Baths
1600-1799 sq-ft

The Majestic Montclair Is Fit For A Royal! Rarely available 3 bedroom unit plus den in a coveted boutique building in stately Forest Hill Village! Ove

50 Photos

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

1.62 km from Davenport Road and Winona Drive

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

Residential Freehold (Detached)

$1899999.0

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

Pre-Construction

Menkes South Lake

193 Nautical Blvd, Oakville

From $2,309,900 to $2,609,900

Project Info

37 Units

Property Mix

Floorplans coming soon

Developer:Menkes Developments Ltd

36 Photos

177 Wallace Avenue, Toronto, ON , MLS #W12464666 , Image - 1

1.76 km from Davenport Road and Winona Drive

177 Wallace Avenue Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12464666

Residential Freehold (Triplex)

$1675000.0

5 +2 Beds
4 Baths
3000-3500 sq-ft

Welcome to 177 Wallace Ave with ***4 Separate Income-Generating Units**** Discover the perfect blend of classic charm and contemporary design in this

41 Photos

1640 Dufferin Street, Toronto, ON , MLS #W12570636 , Image - 1

1.03 km from Davenport Road and Winona Drive

1640 Dufferin Street Corso Italia-Davenport, Toronto, ON MLS® W12570636

Residential Freehold (Multiplex)

$2399000.0

6 +2 Beds
5 Baths
2000-2500 sq-ft

Wonderful investment opportunity in a great neighbourhood completely renovated top to bottom. Excellent rental income, great tenants 5 units in total

50 Photos

914 Dovercourt Road, Toronto, ON , MLS #W12243905 , Image - 1

1.05 km from Davenport Road and Winona Drive

914 Dovercourt Road Dovercourt-Wallace Emerson-Junction, Toronto, ON MLS® W12243905

Residential Freehold (Detached)

$1549900.0

Price drop by 13.8%

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

Live, Rent, or Reimagine-Rare Multi-Unit in Prime West End With One 3000 Sq Ft Of Living Space! Welcome to a fully detached with mutual driveway, char

17 Photos

863 St Clair Avenue W, Toronto, ON , MLS #C12302610 , Image - 1

0.61 km from Davenport Road and Winona Drive

Unit-206, 863 St Clair Avenue W Wychwood, Toronto, ON MLS® C12302610

Residential Condo & Other (Condo Apartment)

$889000.0

2 +1 Beds
2 Baths
700-799 sq-ft

Discover True Urban Luxury at Monza Condos in St. Clair West! Monza Condos redefines boutique living in Toronto's coveted St. Clair West and Wychwood

Pre-Construction

Aquanova Condos

Lakefront Promenade & Lakeshore Road East, Mississauga

Project Info

Units
Condos

Property Mix

Floorplans coming soon

Developer:Greenpark Group

17 Photos

863 St Clair Avenue W, Toronto, ON , MLS #C12302611 , Image - 1

0.61 km from Davenport Road and Winona Drive

Unit-310, 863 St Clair Avenue W Wychwood, Toronto, ON MLS® C12302611

Residential Condo & Other (Condo Apartment)

$1074000.0

2 +1 Beds
2 Baths
800-899 sq-ft

The Ultimate in Modern Living at Monza Condos! Live the urban dream in Monza Condos, ideally located in the vibrant St. Clair West and Wychwood Park n

19 Photos

863 St Clair Avenue W, Toronto, ON , MLS #C12302613 , Image - 1

0.61 km from Davenport Road and Winona Drive

Unit-301, 863 St Clair Avenue W Wychwood, Toronto, ON MLS® C12302613

Residential Condo & Other (Condo Apartment)

$1189000.0

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

Luxury Redefined at Monza Condos in St. Clair West! Elevate your lifestyle at Monza Condos, an exquisite residence situated in the heart of St. Clair

19 Photos

863 St Clair Avenue W, Toronto, ON , MLS #C12302614 , Image - 1

0.61 km from Davenport Road and Winona Drive

Unit-808, 863 St Clair Avenue W Wychwood, Toronto, ON MLS® C12302614

Residential Condo & Other (Condo Apartment)

$1399000.0

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

Penthouse Living at Monza Condos: Unmatched Elegance and Sophistication! Elevate your lifestyle with this exceptional 1,148 sq ft penthouse suite at M

3 Photos

350 Lonsdale Road, Toronto, ON , MLS #C12568506 , Image - 1

1.98 km from Davenport Road and Winona Drive

Unit-614, 350 Lonsdale Road Forest Hill South, Toronto, ON MLS® C12568506

Residential Condo & Other (Condo Apartment)

$1329000.0

2 Beds
2 Baths
1200-1399 sq-ft

Welcome to this bright & spacious, renovated 2 bed/2 bath condo at Lonsdale House, in the heart of Forest Hill Village! Quaint building at the end of

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

31 Photos

11 Shorncliffe Avenue, Toronto, ON , MLS #C12261939 , Image - 1

1.97 km from Davenport Road and Winona Drive

11 Shorncliffe Avenue Casa Loma, Toronto, ON MLS® C12261939

Residential Freehold (Detached)

$4995000.0

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

Welcome to 11 Shorncliffe Ave, a magnificent and completely renovated residence situated on a coveted 45 x 155 south-facing lot, nestled in the tranqu

23 Photos

500 Dupont Street, Toronto, ON , MLS #C12550332 , Image - 1

1.16 km from Davenport Road and Winona Drive

Unit-319, 500 Dupont Street Annex, Toronto, ON MLS® C12550332

Residential Condo & Other (Condo Apartment)

$750000.0

2 Beds
2 Baths
600-699 sq-ft

Welcome to this spacious and well-lit 2-bedroom, 2-bath condo located at Oscar Residences on Bathurst & Dupont. This unit features a south-west facing

Shortlisted Properties

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Maximum 4 project can be compared at one go.

Map View

List View

499 Palmerston Boulevard

Palmerston-Little Italy, Toronto, ON

$2674999.0

380 Macpherson Avenue

Casa Loma, Toronto, ON

$459000.0

1420 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$449000.0

1113 Dufferin Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1090000.0

215 Lonsmount Drive

Forest Hill South, Toronto, ON

$5380000.0

17 Ardwold Gate

Casa Loma, Toronto, ON

$34500000.0

1083 Dupont Street

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1628600.0

11 Foundry Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$940000.0

447 Walmer Road

Forest Hill South, Toronto, ON

$1899900.0

157 Glenholme Avenue

Oakwood Village, Toronto, ON

$1549900.0

253 Albany Avenue

Annex, Toronto, ON

$2095000.0

351 Clinton Street

Palmerston-Little Italy, Toronto, ON

$2248800.0

52 Nina Street

Casa Loma, Toronto, ON

$2198000.0

40 Westmoreland Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1748000.0

185 Alberta Avenue

Oakwood Village, Toronto, ON

$1295000.0

185 Alberta Avenue

Oakwood Village, Toronto, ON

$1095000.0

1943 Dufferin Street

Corso Italia-Davenport, Toronto, ON

$899000.0

497 Brunswick Avenue

Annex, Toronto, ON

$3495000.0

70 Montclair Avenue W

Forest Hill South, Toronto, ON

$1248000.0

388 Oakwood Avenue

Oakwood Village, Toronto, ON

$1899999.0

177 Wallace Avenue

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1675000.0

1640 Dufferin Street

Corso Italia-Davenport, Toronto, ON

$2399000.0

914 Dovercourt Road

Dovercourt-Wallace Emerson-Junction, Toronto, ON

$1549900.0

863 St Clair Avenue W

Wychwood, Toronto, ON

$889000.0

863 St Clair Avenue W

Wychwood, Toronto, ON

$1074000.0

863 St Clair Avenue W

Wychwood, Toronto, ON

$1189000.0

863 St Clair Avenue W

Wychwood, Toronto, ON

$1399000.0

350 Lonsdale Road

Forest Hill South, Toronto, ON

$1329000.0

11 Shorncliffe Avenue

Casa Loma, Toronto, ON

$4995000.0

500 Dupont Street

Annex, Toronto, ON

$750000.0

House for Sale near Davenport Road and Winona Drive, C02

Rosehaven Ivy Rouge

Rosehaven Simcoe Woods

Angus Glen South Village

The Platform at Station Park

Menkes South Lake

Aquanova Condos

1515 Pickering Parkway

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