Cookstown, Innisfil, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Cookstown. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Cookstown

Last Updated: December 19, 2025

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22 EAST JOHN Street, Simcoe, ON , MLS #N12454213 , Image - 1

22 EAST JOHN Street Cookstown, Innisfil, Simcoe, ON MLS® N12454213

Residential Freehold (Detached)

$2149000.0

3 +2 Beds
5 Baths
3000-3500 sq-ft

BACKS ONTO PROTECTED LAND. This stunning luxury home is situated on a quiet dead-end st, w/views of the countryside, + steps from park/rink/courts/lib

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1, 3, 5 Church Street, Simcoe, ON , MLS #N12084695 , Image - 1

1, 3, 5 Church Street Cookstown, Innisfil, Simcoe, ON MLS® N12084695

Residential Freehold (Store W Apartment/Office)

$2200000.0

6 Beds
5 Baths
5000 + sq-ft

Tremendous Investment Opportunity in the heart of Cookstown w/ 2 Buildings, a parking lot, 5 Apartments, a commercial space and a Restaurant! Located

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3568 4 Line, Simcoe, ON , MLS #N12641382 , Image - 1

3568 4 Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12641382

Residential Freehold (Vacant Land)

$3500000.0

Are you ready to turn your real estate dreams into reality? Presenting a golden opportunity for savvy investors - a sprawling piece of vacant land nes

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8464 6th Line, Simcoe, ON , MLS #N12638712 , Image - 1

8464 6th Line Rural Essa, Essa, Simcoe, ON MLS® N12638712

Residential Freehold (Detached)

$2500000.0

4 Beds
3 Baths
3500-5000 sq-ft

TIMBER-FRAME ESTATE ON 10 ACRES WITH INGROUND POOL, EXPANSIVE BARN, VERSATILE OUTBUILDINGS, & A 4,544 SQ FT HOME BUILT TO IMPRESS! Call it a farmhouse