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Houses for Sale near Winston Churchill Collegiate Institute in Dorset Park, Toronto

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On the Square Yards page, you will find a diverse selection of houses for sale near Winston Churchill Collegiate Institute. Our platform understands diverse needs and offers a wide range of properties, from freehold and commercial spaces to condo houses. Whether you're seeking modern living spaces or classic designs, our listings cater to all preferences. Simply filter properties by price, number of bedrooms (1 - 4+), bathrooms, and amenities like gyms and pools. Discover the houses for sale near Winston Churchill Collegiate Institute from budget-friendly options that you can easily filter out for your convenience. Start your journey to finding your perfect home today.

Last Updated: April 04, 2026

5 Photos

56 Martindale Road, Toronto, ON , MLS #E12754668 , Image - 1

4.18 km from Winston Churchill Collegiate Institute

56 Martindale Road Cliffcrest, Toronto, ON MLS® E12754668

Residential Freehold (Detached)

$1304100.0

Price drop by 8.0%

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

Being Sold in As Is Condition. Upper Bluffs Home On a Large Premium Lot (52X182) In The Cliffcrest Neighborhood. This Detached House Has A Large Eat-I

2 Photos

1972 Brimley Road, Toronto, ON , MLS #E12581836 , Image - 1

4.13 km from Winston Churchill Collegiate Institute

1972 Brimley Road Agincourt South-Malvern West, Toronto, ON MLS® E12581836

Residential Freehold (Vacant Land)

$950000.0

3 Beds
2 Baths
1100-1500 sq-ft

Attention Builders/Investors! Don't Miss This Rare Opportunity To Build income rental property. will be Sale together with 1970 Brimley rd LOT . 2 lot

2 Photos

1970 Brimley Road, Toronto, ON , MLS #E12581746 , Image - 1

4.13 km from Winston Churchill Collegiate Institute

1970 Brimley Road Agincourt South-Malvern West, Toronto, ON MLS® E12581746

Residential Freehold (Detached)

$950000.0

3 Beds
2 Baths
1100-1500 sq-ft

Attention Builders/Investors! Don't Miss This Rare Opportunity To Build income rental property. will be Sale together with 1972 Brimley rd LOT . 2 lot

27 Photos

1328 Birchmount Road, Toronto, ON , MLS #E12955844 , Image - 1

0.65 km from Winston Churchill Collegiate Institute

Unit-1701, 1328 Birchmount Road Wexford-Maryvale, Toronto, ON MLS® E12955844

Residential Condo & Other (Condo Apartment)

$539000.0

2 Beds
2 Baths
900-999 sq-ft

Beautiful Bright South Facing 2-Bedroom, 2-Bathroom Suite With 9-Foot Ceilings and Floor to Ceiling Windows! Perfect for Young Professional with itsOp

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

44 Photos

238 Bonis Avenue, Toronto, ON , MLS #E12950928 , Image - 1

4.32 km from Winston Churchill Collegiate Institute

Unit-1118, 238 Bonis Avenue Tam O'Shanter-Sullivan, Toronto, ON MLS® E12950928

Residential Condo & Other (Condo Apartment)

$670000.0

3 Beds
2 Baths
1200-1399 sq-ft

Tridel Built, Large, Sun-Filled Corner Unit 1,280 S.F. Laminate Flooring, Crown-Molding, Fully Furnished-Move In & Enjoy. Parking & Locker Included. A

29 Photos

181 Village Green Square, Toronto, ON , MLS #E12854750 , Image - 1

3.45 km from Winston Churchill Collegiate Institute

Unit-314, 181 Village Green Square Agincourt South-Malvern West, Toronto, ON MLS® E12854750

Residential Condo & Other (Condo Apartment)

$574800.0

Price drop by 2.2%

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

Rare Find 10 ft ceiling,never use an elevator with 2 car side by side same level 3rd floor semi enclosed parking that can fit a full size pick up, sma

40 Photos

10 Pastrano Court, Toronto, ON , MLS #E12923860 , Image - 1

4.02 km from Winston Churchill Collegiate Institute

10 Pastrano Court Cliffcrest, Toronto, ON MLS® E12923860

Residential Freehold (Detached)

$929000.0

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

Bright, Spacious & Income-Generating! This Beautifully Maintained Detached Bungalow Is Nestled On A Private Court In A Family-Friendly Neighbourhood.

36 Photos

14 Flora Drive, Toronto, ON , MLS #E12926446 , Image - 1

0.66 km from Winston Churchill Collegiate Institute

14 Flora Drive Dorset Park, Toronto, ON MLS® E12926446

Residential Freehold (Detached)

$789900.0

6 +3 Beds
4 Baths
2000-2500 sq-ft

Wonderful Home In The Dorset Park Area! Hardwood Floors Throughout The Main Floor.This Home Is The Perfect Investment Property Or Large Family With A

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

1 Photos

10 Deerlick Court, Toronto, ON

4.49 km from Winston Churchill Collegiate Institute

Unit-713, 10 Deerlick Court Parkwoods-Donalda, Toronto, ON MLS® C12856042

Residential Condo & Other (Condo Apartment)

$488000.0

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

Newer Condo With Luxurious Finishings, Conveniently Located At York Mills/DVP And TTC At Doorstep. Spacious One Bedroom Plus Den That Can Be Used As A

16 Photos

185 Bonis Avenue, Toronto, ON , MLS #E12905888 , Image - 1

4.34 km from Winston Churchill Collegiate Institute

Unit-1506, 185 Bonis Avenue Tam O'Shanter-Sullivan, Toronto, ON MLS® E12905888

Residential Condo & Other (Condo Apartment)

$618000.0

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

Large 2 Bdrm+Den ! Bright Corner Unit With Unobstructed South-West View! Suite area 836 sq/ft, Balcony area 34 sq/ft , total 870 Sq.ft. Two bedrooms a

45 Photos

126 Portsdown Road, Toronto, ON , MLS #E12774352 , Image - 1

1.18 km from Winston Churchill Collegiate Institute

126 Portsdown Road Dorset Park, Toronto, ON MLS® E12774352

Residential Freehold (Detached)

$1197900.0

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

Stunning Fully Renovated Income-Generating Home - Turnkey Opportunity! Newly & legally renovated top-to-bottom open-concept home with excellent income

33 Photos

181 Wynford Drive, Toronto, ON , MLS #C12947264 , Image - 1

4.77 km from Winston Churchill Collegiate Institute

Unit-2607, 181 Wynford Drive Banbury-Don Mills, Toronto, ON MLS® C12947264

Residential Condo & Other (Condo Apartment)

$799000.0

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

Bright Gorgeously Renovated CORNER UNIT. ENLARGED Kitchen, Open Concept. This Suite Was Originally a 2+1. It has Been Elegantly Reimagined into a Spac

14 Photos

100 Dundalk Drive, Toronto, ON , MLS #E12946830 , Image - 1

2.59 km from Winston Churchill Collegiate Institute

Unit-1003, 100 Dundalk Drive Dorset Park, Toronto, ON MLS® E12946830

Residential Condo & Other (Condo Apartment)

$390000.0

2 Beds
1 Baths
800-899 sq-ft

Perfect Condo Unit to Set Up Own Life. Located Conveniently Near 401 & Kennedy Rd, Close to TTC Bus Stops, Walking Distance to Schools, Metro and High

16 Photos

2031 Kennedy Road, Toronto, ON , MLS #E12945868 , Image - 1

3.27 km from Winston Churchill Collegiate Institute

Unit-2523, 2031 Kennedy Road Agincourt South-Malvern West, Toronto, ON MLS® E12945868

Residential Condo & Other (Condo Apartment)

$389000.0

1 Beds
1 Baths
0-499 sq-ft

BUILDER INVENTORY! Eligible For New Home FTHB Rebate.* One Bedroom Functional Layout. LightFilled Bedroom And A Perfect Balcony With East Views. All A

28 Photos

66 Sonmore Drive, Toronto, ON , MLS #E12865544 , Image - 1

3.99 km from Winston Churchill Collegiate Institute

66 Sonmore Drive Agincourt South-Malvern West, Toronto, ON MLS® E12865544

Residential Freehold (Detached)

$1058000.0

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

Welcome to 66 Snomre Drive - a beautifully maintained 4+1 bedroom home situated on a premium 45 x 132 ft lot in one of Scarborough's most sought-after

30 Photos

282B Aylesworth Avenue, Toronto, ON , MLS #E12943330 , Image - 1

4.91 km from Winston Churchill Collegiate Institute

282B Aylesworth Avenue Birchcliffe-Cliffside, Toronto, ON MLS® E12943330

Residential Freehold (Detached)

$1400000.0

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

Luxurious Custom Home in Prime Location! This Stunning 4+1 Bedroom, 4.5 bathroom Custom-Built Home Offers The Perfect Blend Of Elegance And Functional

44 Photos

1051 Victoria Pk Avenue, Toronto, ON , MLS #E12942680 , Image - 1

4.84 km from Winston Churchill Collegiate Institute

1051 Victoria Pk Avenue Clairlea-Birchmount, Toronto, ON MLS® E12942680

Residential Freehold (Multiplex)

$5750000.0

9 +9 Beds
12 Baths
< 700 sq-ft

Wonderful Investment Opportunity 12 Unit Building Completely Renovated With Excellent Rental Income In Suite Laundry in each unit New Stainless Steel

29 Photos

6 Archibald Mews, Toronto, ON , MLS #E12940552 , Image - 1

1.21 km from Winston Churchill Collegiate Institute

6 Archibald Mews Bendale, Toronto, ON MLS® E12940552

Residential Freehold (Att/Row/Townhouse)

$859000.0

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

This Four Bedroom Four Washroom Townhouse Is A Must See Home! Very Well Maintained Loads Of Upgrades!!! Located In The Sought After Bendale Community,

23 Photos

20 Bypass Court, Toronto, ON , MLS #E12939982 , Image - 1

3.42 km from Winston Churchill Collegiate Institute

20 Bypass Court Tam O'Shanter-Sullivan, Toronto, ON MLS® E12939982

Residential Freehold (Detached)

$999999.0

3 Beds
2 Baths
1100-1500 sq-ft

The home is situated in a court surrounded with excellent school district and a family-friendly neighborhood in addition to having easy access to high

15 Photos

30 Meadowglen Place, Toronto, ON , MLS #E12903942 , Image - 1

4.84 km from Winston Churchill Collegiate Institute

Unit-1408, 30 Meadowglen Place Woburn, Toronto, ON MLS® E12903942

Residential Condo & Other (Condo Apartment)

$448000.0

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

Welcome to this impeccably maintained and truly exceptional condo, ideally located in the heart of the highly sought-after Woburn community. Step insi

39 Photos

39 Treadgold Crescent, Toronto, ON , MLS #C12832198 , Image - 1

3.8 km from Winston Churchill Collegiate Institute

39 Treadgold Crescent Parkwoods-Donalda, Toronto, ON MLS® C12832198

Residential Freehold (Detached)

$1248880.0

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

This tastefully updated bungalow on a quiet crescent, located in a highly sought-after neighbourhood, combines contemporary design with everyday pract

25 Photos

295 Village Green Square, Toronto, ON , MLS #E12912560 , Image - 1

3.45 km from Winston Churchill Collegiate Institute

Unit-67, 295 Village Green Square Agincourt South-Malvern West, Toronto, ON MLS® E12912560

Residential Condo & Other (Condo Townhouse)

$599000.0

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

Located in the heart of Scarborough, Spacious 3+1 bedroom townhome in Tridels Metrogate Community offers both comfort and convenience. Newly Painted a

35 Photos

40 Lombardy Crescent, Toronto, ON , MLS #E12932004 , Image - 1

3.02 km from Winston Churchill Collegiate Institute

40 Lombardy Crescent Kennedy Park, Toronto, ON MLS® E12932004

Residential Freehold (Detached)

$969900.0

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

Welcome to In High Demand Kennedy Park Neighborhood at Scarborough. Quiet and Beautiful Community Close To High Demand High School- R.H. King Academy,

19 Photos

178 Three Valleys Drive, Toronto, ON , MLS #C12936012 , Image - 1

4.85 km from Winston Churchill Collegiate Institute

178 Three Valleys Drive Parkwoods-Donalda, Toronto, ON MLS® C12936012

Residential Freehold (Semi-Detached )

$1179000.0

3 Beds
2 Baths
1100-1500 sq-ft

Discover the perfect blend of modern comfort and unparalleled outdoor access at 178 Three Valleys Drive in the heart of Parkwoods-Donalda.This beautif

48 Photos

1533 O'Connor Drive, Toronto, ON , MLS #E12852460 , Image - 1

4.35 km from Winston Churchill Collegiate Institute

1533 O'Connor Drive O'Connor-Parkview, Toronto, ON MLS® E12852460

Residential Freehold (Store W Apartment/Office)

$1270000.0

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

Excellent Opportunity to Own a Mixed Use Property - Live and Work, with Two Residential Rental Units and a Commercial Main Floor Unit with Great Expos

32 Photos

1720 Eglinton Avenue E, Toronto, ON , MLS #C12853752 , Image - 1

3.62 km from Winston Churchill Collegiate Institute

Unit-108, 1720 Eglinton Avenue E Victoria Village, Toronto, ON MLS® C12853752

Residential Condo & Other (Condo Apartment)

$529999.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome To This Stunning Two-Bedroom, Two-Bathroom Loft-Style Suite That Seamlessly Blends Style, Comfort, And Everyday Convenience. Offering Over 1,1

50 Photos

185 Bonis Avenue, Toronto, ON , MLS #E12929012 , Image - 1

4.34 km from Winston Churchill Collegiate Institute

Unit-1511, 185 Bonis Avenue Tam O'Shanter-Sullivan, Toronto, ON MLS® E12929012

Residential Condo & Other (Condo Apartment)

$599000.0

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

Welcome to this Bright and spacious 2 bedroom + den suite, offering 2 full bathrooms and approximately 858 sq. ft. living space with 1 parking and 1 l

30 Photos

94 Laurentide Drive, Toronto, ON , MLS #C12655116 , Image - 1

4.97 km from Winston Churchill Collegiate Institute

94 Laurentide Drive Parkwoods-Donalda, Toronto, ON MLS® C12655116

Residential Freehold (Detached)

$3800000.0

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

Luxury Architectural Retreat in the Exclusive Donalda Golf Club Enclave - Set in one of Torontos most prestigious neighborhoods, this bespoke residenc

44 Photos

84B Tisdale Avenue, Toronto, ON , MLS #C12887544 , Image - 1

3.64 km from Winston Churchill Collegiate Institute

84B Tisdale Avenue Victoria Village, Toronto, ON MLS® C12887544

Residential Freehold (Att/Row/Townhouse)

$875000.0

Price drop by 2.2%

5 Beds
4 Baths
1500-2000 sq-ft

With over 1,500 square feet of thoughtfully designed living space, this spacious end-unit townhome offers the feel of a semi-detached home. Featuring

2 Photos

22 Hopecrest Crescent, Toronto, ON , MLS #E12929738 , Image - 1

2.72 km from Winston Churchill Collegiate Institute

22 Hopecrest Crescent Kennedy Park, Toronto, ON MLS® E12929738

Residential Freehold (Detached)

$849000.0

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

Tucked away on a quiet crescent, 22 Hopecrest Crescent is the kind of opportunity that rarely comes along. A beautifully maintained 3+Den bungalow off

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.

Map View

List View

56 Martindale Road, Toronto, ON , MLS #E12754668 , Image - 1

56 Martindale Road

Cliffcrest, Toronto, ON

$1304100.0

1972 Brimley Road, Toronto, ON , MLS #E12581836 , Image - 1

1972 Brimley Road

Agincourt South-Malvern West, Toronto, ON

$950000.0

1970 Brimley Road, Toronto, ON , MLS #E12581746 , Image - 1

1970 Brimley Road

Agincourt South-Malvern West, Toronto, ON

$950000.0

1328 Birchmount Road, Toronto, ON , MLS #E12955844 , Image - 1

1328 Birchmount Road

Wexford-Maryvale, Toronto, ON

$539000.0

238 Bonis Avenue, Toronto, ON , MLS #E12950928 , Image - 1

238 Bonis Avenue

Tam O'Shanter-Sullivan, Toronto, ON

$670000.0

181 Village Green Square, Toronto, ON , MLS #E12854750 , Image - 1

181 Village Green Square

Agincourt South-Malvern West, Toronto, ON

$574800.0

10 Pastrano Court, Toronto, ON , MLS #E12923860 , Image - 1

10 Pastrano Court

Cliffcrest, Toronto, ON

$929000.0

14 Flora Drive, Toronto, ON , MLS #E12926446 , Image - 1

14 Flora Drive

Dorset Park, Toronto, ON

$789900.0

10 Deerlick Court, Toronto, ON , MLS #C12856042 , Image - 1

10 Deerlick Court

Parkwoods-Donalda, Toronto, ON

$488000.0

185 Bonis Avenue, Toronto, ON , MLS #E12905888 , Image - 1

185 Bonis Avenue

Tam O'Shanter-Sullivan, Toronto, ON

$618000.0

126 Portsdown Road, Toronto, ON , MLS #E12774352 , Image - 1

126 Portsdown Road

Dorset Park, Toronto, ON

$1197900.0

181 Wynford Drive, Toronto, ON , MLS #C12947264 , Image - 1

181 Wynford Drive

Banbury-Don Mills, Toronto, ON

$799000.0

100 Dundalk Drive, Toronto, ON , MLS #E12946830 , Image - 1

100 Dundalk Drive

Dorset Park, Toronto, ON

$390000.0

2031 Kennedy Road, Toronto, ON , MLS #E12945868 , Image - 1

2031 Kennedy Road

Agincourt South-Malvern West, Toronto, ON

$389000.0

66 Sonmore Drive, Toronto, ON , MLS #E12865544 , Image - 1

66 Sonmore Drive

Agincourt South-Malvern West, Toronto, ON

$1058000.0

282B Aylesworth Avenue, Toronto, ON , MLS #E12943330 , Image - 1

282B Aylesworth Avenue

Birchcliffe-Cliffside, Toronto, ON

$1400000.0

1051 Victoria Pk Avenue, Toronto, ON , MLS #E12942680 , Image - 1

1051 Victoria Pk Avenue

Clairlea-Birchmount, Toronto, ON

$5750000.0

6 Archibald Mews, Toronto, ON , MLS #E12940552 , Image - 1

6 Archibald Mews

Bendale, Toronto, ON

$859000.0

20 Bypass Court, Toronto, ON , MLS #E12939982 , Image - 1

20 Bypass Court

Tam O'Shanter-Sullivan, Toronto, ON

$999999.0

30 Meadowglen Place, Toronto, ON , MLS #E12903942 , Image - 1

30 Meadowglen Place

Woburn, Toronto, ON

$448000.0

39 Treadgold Crescent, Toronto, ON , MLS #C12832198 , Image - 1

39 Treadgold Crescent

Parkwoods-Donalda, Toronto, ON

$1248880.0

295 Village Green Square, Toronto, ON , MLS #E12912560 , Image - 1

295 Village Green Square

Agincourt South-Malvern West, Toronto, ON

$599000.0

40 Lombardy Crescent, Toronto, ON , MLS #E12932004 , Image - 1

40 Lombardy Crescent

Kennedy Park, Toronto, ON

$969900.0

178 Three Valleys Drive, Toronto, ON , MLS #C12936012 , Image - 1

178 Three Valleys Drive

Parkwoods-Donalda, Toronto, ON

$1179000.0

1533 O'Connor Drive, Toronto, ON , MLS #E12852460 , Image - 1

1533 O'Connor Drive

O'Connor-Parkview, Toronto, ON

$1270000.0

1720 Eglinton Avenue E, Toronto, ON , MLS #C12853752 , Image - 1

1720 Eglinton Avenue E

Victoria Village, Toronto, ON

$529999.0

185 Bonis Avenue, Toronto, ON , MLS #E12929012 , Image - 1

185 Bonis Avenue

Tam O'Shanter-Sullivan, Toronto, ON

$599000.0

94 Laurentide Drive, Toronto, ON , MLS #C12655116 , Image - 1

94 Laurentide Drive

Parkwoods-Donalda, Toronto, ON

$3800000.0

84B Tisdale Avenue, Toronto, ON , MLS #C12887544 , Image - 1

84B Tisdale Avenue

Victoria Village, Toronto, ON

$875000.0

22 Hopecrest Crescent, Toronto, ON , MLS #E12929738 , Image - 1

22 Hopecrest Crescent

Kennedy Park, Toronto, ON

$849000.0

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