Houses for Sale in Cheltenham Caledon Under $10 Million

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Looking for houses under $10m 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 $10m 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 $10m, including freehold properties, condos, and commercial spaces.

Last Updated: November 14, 2026

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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

50 Photos

114 Kennedy Road, Peel, ON , MLS #W14105554 , Image - 1

114 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W14105554

Residential Freehold (Detached)

$899995.0

3 Beds
2 Baths
1100-1500 sq-ft

OPEN HOUSE SUNDAY NOVEMBER 8, 1-3PM Now offered well below original purchase price with additional negotiable bonus incentive!!! This beautifully m

50 Photos

84 Kennedy Road, Peel, ON , MLS #W13771530 , Image - 1

84 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W13771530

Residential Freehold (Detached)

$2899000.0

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

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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.

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5025 Four Springs Avenue, Peel, ON , MLS #W14180738 , Image - 1

Unit-2104, 5025 Four Springs Avenue Hurontario, Mississauga, Peel, ON MLS® W14180738

Residential Condo & Other (Condo Apartment)

$629900.0

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

Enjoy elevated condo living in this bright and spacious 2-bedroom plus den suite at Pinnacle Uptown, 5025 Four Springs Avenue! Situated on the 21st fl

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