Houses for Sale in Cheltenham Caledon Under $5 Million

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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: December 05, 2025

38 Photos

50 Lyonsview Lane, Peel, ON , MLS #W12330251 , Image - 1

50 Lyonsview Lane Cheltenham, Caledon, Peel, ON MLS® W12330251

Residential Freehold (Detached)

$2549900.0

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

Welcome To The Village Of Cheltenham! This Stunning Executive Estate Sits At The End Of The Coveted Lyonsview Lane Cul-De-Sac. Luxuriously Renovated,

46 Photos

57 Kennedy Road, Peel, ON , MLS #W12092509 , Image - 1

57 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® W12092509

Residential Freehold (Detached)

$2679000.0

4 Beds
6 Baths
3500-5000 sq-ft

Welcome to your next chapter! This rare gem of an estate is a chance to have your dream home on the perfect secluded lot, still close to the city. Thi

43 Photos

57 Kennedy Road, Peel, ON , MLS #40719468 , Image - 1

57 Kennedy Road Cheltenham, Caledon, Peel, ON MLS® 40719468

Residential (Single Family Residence)

$2679000

4 Beds
7 Baths
6861 sq-ft

Discover a property that redefines luxury living for the discerning buyer seeking something truly special. This exceptional estate invites you to expe

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45 Photos

2525 Trident Avenue, Peel, ON , MLS #W12489282 , Image - 1

2525 Trident Avenue Cooksville, Mississauga, Peel, ON MLS® W12489282

Residential Freehold (Semi-Detached )

$890000.0

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

Rare Opportunity! Spacious 5-Level Backsplit Semi with Incredible Income Potential Ideal for Savvy Investors or Multi-Generational Living. Featuring a

22 Photos

46 Mint Leaf Boulevard, Peel, ON , MLS #W12556332 , Image - 1

46 Mint Leaf Boulevard Sandringham-Wellington, Brampton, Peel, ON MLS® W12556332

Residential Freehold (Detached)

$1069900.0

3 +2 Beds
4 Baths
2000-2500 sq-ft

Welcome to this newly painted 3-bedroom gem nestled in one of Brampton's most sought-after communities. The grand 20 ft entrance sets the tone the mom

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