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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 17, 2025

50 Photos

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

33 Photos

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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40 Photos

1372 Division Road E, Simcoe, ON , MLS #S12517032 , Image - 1

1372 Division Road E Rural Severn, Severn, Simcoe, ON MLS® S12517032

Residential Freehold (Detached)

$2199000.0

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

INDULGE IN LUXURY ON 2.1 ACRES WITH BREATHTAKING VIEWS, SHARED OWNERSHIP OF AN ADDITIONAL 32 ACRES, & A MAN-MADE LAKE!! Enter a realm of unrivalled el

40 Photos

130 Concession 15 N/A W, Simcoe, ON , MLS #S12424833 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S12424833

Residential Freehold (Detached)

$2599000.0

4 Beds
3 Baths
3500-5000 sq-ft

Your Dream Country Retreat! Experience the perfect blend of luxury, functionality, and self-sufficiency on this breathtaking 40-acre estate. Thoughtfu

Pre-Construction

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard

From $879,990 - $1,339,990

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes

25 Photos

7475 Poplar Side Road, Simcoe, ON , MLS #S12383439 , Image - 1

7475 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12383439

Residential Freehold (Vacant Land)

$7500000.0

1 Baths
1100-1500 sq-ft

Future Development Opportunity on 84.6 acres on Poplar Sideroad with the Pretty River flowing through the land and abutting the Train Trail. A very bu

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Cookstown, Innisfil, ON Luxury Homes

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Rosehaven Simcoe Woods

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