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 19, 2025

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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,

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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

Similar Properties near Cheltenham

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35 York Street, Peel, ON , MLS #W12378714 , Image - 1

35 York Street Malton, Mississauga, Peel, ON MLS® W12378714

Residential Freehold (Detached)

$850000.0

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

Bright & Spacious Family Home on a Premium Lot! Welcome to this beautifully maintained five (5) bedroom detached home situated on a massive 105.5 ft x

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580 Shoreline Drive, Peel, ON , MLS #W12569814 , Image - 1

Unit-6, 580 Shoreline Drive Cooksville, Mississauga, Peel, ON MLS® W12569814

Residential Condo & Other (Condo Townhouse)

$699000.0

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

Bright and updated upper-level stacked townhouse with a large south-facing terrace, featuring 2 spacious bedrooms plus a versatile roof-level loft, an

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1825 Hyde Mill Crescent, Peel, ON , MLS #W12642098 , Image - 1

1825 Hyde Mill Crescent Streetsville, Mississauga, Peel, ON MLS® W12642098

Residential Condo & Other (Detached Condo)

$799800.0

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

Welcome to Hyde Mill's finest. This chic and unique detached condo executive townhouse has the best credit river views in the complex. Rare cul-de-sac

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