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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: February 12, 2026

50 Photos

1428 Mill Street, Peel, ON , MLS #W12725402 , Image - 1

1428 Mill Street Cheltenham, Caledon, Peel, ON MLS® W12725402

Residential Freehold (Detached)

$1149500.0

3 Beds
2 Baths
1500-2000 sq-ft

Nestled in the charming town of Cheltenham, Ontario, this stunning 2-storey, 3-bedroom, 2-bathroom home on sought-after quiet Mill Street offers the p

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50 Photos

22 Rolling Rock Way, Peel, ON , MLS #W12658714 , Image - 1

22 Rolling Rock Way Bram West, Brampton, Peel, ON MLS® W12658714

Residential Freehold (Detached)

$1468000.0

Price drop by 8.2%

4 Beds
4 Baths
3000-3500 sq-ft

Luxurious 4-Bedroom, 4-Bathroom Detached Home offering over 3,000 square feet of luxurious living space above grade. Built in 2020, this elegant resid

9 Photos

86 Dundas Street E, Peel, ON , MLS #W12785102 , Image - 1

Unit-821, 86 Dundas Street E Cooksville, Mississauga, Peel, ON MLS® W12785102

Residential Condo & Other (Condo Apartment)

$569000.0

1 +1 Beds
1 Baths
500-599 sq-ft

Stunning 1 Bedroom + Den, 1 Bath suite in the Artform High-Rise by Emblem Developments, located in desirable Cooksville. Bright, open-concept living a

33 Photos

33 Campbell Drive, Peel, ON , MLS #W12742516 , Image - 1

33 Campbell Drive Northwood Park, Brampton, Peel, ON MLS® W12742516

Residential Freehold (Detached)

$799000.0

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

Outstanding opportunity for investors and large or multi-generational families! Registered duplex as per MPAC/GeoWarehouse situated on a massive appro

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150 Joymar Drive, Peel, ON , MLS #W12784870 , Image - 1

Unit-TH94, 150 Joymar Drive Streetsville, Mississauga, Peel, ON MLS® W12784870

Residential Condo & Other (Condo Townhouse)

$800000.0

3 Beds
2 Baths
1800-1999 sq-ft

Welcome to this sun-filled end-unit townhome, perfectly positioned in the heart of the highly coveted Streetsville community and within the top-ranked

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Houses for Sale in Cheltenham Caledon Under $5 Million

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