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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 29, 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

Similar Properties near Cookstown

23 Photos

10 White Oaks Road, Simcoe, ON , MLS #S12378091 , Image - 1

10 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S12378091

Residential Freehold (Detached)

$3350000.0

5 Beds
4 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Welcome to an exceptional waterfront retreat, boasting over 91' of pristine sandy shoreline and a steel reta

40 Photos

20 Tiny Beaches Road N, Simcoe, ON , MLS #S12647006 , Image - 1

20 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S12647006

Residential Freehold (Detached)

$2199900.0

4 +3 Beds
4 Baths
2500-3000 sq-ft

This exceptional 0.8-acre waterfront Georgian Bay estate offers 270-degree water views and breathtaking sunsets. The meticulously maintained 2,818 sqf

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

35 Photos

1614 Ridge Road E, Simcoe, ON , MLS #S6142920 , Image - 1

1614 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S6142920

Residential Freehold (Multiplex)

$3299000.0

Price drop by 1.8%

6 Beds
5 Baths
5000 + sq-ft

Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This U

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Cookstown, Innisfil, ON Luxury Homes

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Rosehaven Simcoe Woods

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