minPriceVal

maxPriceVal

minSize

maxSize

Houses for Sale in Cheltenham Caledon Under $5 Million

Showing results 1 - 10 of 10

Looking for houses under $5m for sale in Cheltenham, Caledon? With Square Yards Canada, discover a vast range of properties within your budget in Cheltenham across Toronto. If you plan to buy houses under $5m in Cheltenham, Caledon, you can refine your search by property size, specific amenities, and property age. Filter the listings by the number of bedrooms, bathrooms, and surface area to match your requirements. Our listings feature a wide range of Cheltenham houses for sale under $5m, including freehold properties, condos, and commercial spaces.

Last Updated: August 13, 2026

50 Photos

114 Kennedy Road, Peel, ON , MLS #W13514108 , Image - 1

114 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13514108

Residential Freehold (Detached)

$1149000.0

Price drop by 4.2%

3 Beds
2 Baths
1100-1500 sq-ft

OPEN HOUSE SATURDAY AUGUST 15th 1-3PM Welcome to this beautifully maintained bungalow offering the perfect blend of comfort, convenience, and except

Open House : Sat Aug 15, 12:00 PM to 02:00 PM

41 Photos

14700 Creditview Road, Peel, ON , MLS #W13428472 , Image - 1

14700 Creditview Road Cheltenham, Caledon, Peel, ON MLS® W13428472

Residential Freehold (Detached)

$1999900.0

4 Beds
3 Baths
3500-5000 sq-ft

Welcome to a truly exceptional country estate nestled in the heart of Cheltenham, One of Caledon's most picturesque and historic villages. Set on a pr

35 Photos

1510 Station Road, Peel, ON , MLS #W13612054 , Image - 1

1510 Station Road Cheltenham, Caledon, Peel, ON MLS® W13612054

Residential Freehold (Detached)

$999900.0

4 Beds
2 Baths
1500-2000 sq-ft

Welcome to 1510 Station Road, a beautifully updated home in the heart of Cheltenham, set on a rare 0.344-acre lot (~15,000 sq. ft.) surrounded by gard

24 Photos

2424 Olde Base Line Road, Peel, ON , MLS #W13204878 , Image - 1

2424 Olde Base Line Road Cheltenham, Caledon, Peel, ON MLS® W13204878

Residential Freehold (Detached)

$749900.0

Price drop by 6.3%

1 Beds
1 Baths
< 700 sq-ft

Welcome to your own 'Paradise in Caledon' a charming home set on over 1.25 acre with the CreditRiver running through this serene property. Featuring a

33 Photos

1442 Mill Street, Peel, ON , MLS #W13551760 , Image - 1

1442 Mill Street Cheltenham, Caledon, Peel, ON MLS® W13551760

Residential Freehold (Detached)

$699999.0

3 Beds
2 Baths
700-1100 sq-ft

Charming 3-Bedroom Home in the Heart of Historic Cheltenham Nestled in the picturesque village of Cheltenham, this inviting 3-bedroom, 2bath, two-stor

50 Photos

26 Kennedy Road, Peel, ON , MLS #W13220846 , Image - 1

26 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13220846

Residential Freehold (Detached)

$1285000.0

Price drop by 3.0%

4 Beds
2 Baths
2000-2500 sq-ft

Welcome to 26 Kennedy Road - where peaceful country living meets everyday comfort, just minutes from the city. Nestled on approximately 2/3 of an acre

46 Photos

57 Kennedy Road, Peel, ON , MLS #W13505786 , Image - 1

57 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13505786

Residential Freehold (Detached)

$2500000.0

4 Beds
6 Baths
3500-5000 sq-ft

Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special.

30 Photos

104 Kennedy Road, Peel, ON , MLS #W13452590 , Image - 1

104 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13452590

Residential Freehold (Detached)

$1978500.0

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

Potential For 3 Separate Building Lots. One Of Cheltenham's Most Private Estates, 2 Acres, With An Amazing 200 Feet Frontage, Has The Enjoyment Of Ove

50 Photos

84 Kennedy Road, Peel, ON , MLS #W12394471 , Image - 1

84 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W12394471

Residential Freehold (Detached)

$2998000.0

Price drop by 10.5%

5 +1 Beds
6 Baths
5000 + sq-ft

Timeless elegance meets impeccable craftsmanship in this stunning Cheltenham estate. A rare find, this beautifully built 5+1 bed, 6 bath home in the s

6 Photos

13171 Chinguacousy Road, Peel, ON , MLS #W12791312 , Image - 1

13171 Chinguacousy Road Cheltenham, Caledon, Peel, ON MLS® W12791312

Residential Freehold (Detached)

$4399000.0

3 +0 Beds
2 Baths
1100-1500 sq-ft

Prime 10-Acre Parcel In An Expanding Caledon Location Featuring Clear, Level, And Highly Usable Land. Situated At The Corner Of Chinguacousy Road And

Shortlisted Properties

Error

Maximum 4 project can be compared at one go.