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: September 24, 2026

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128 Copeland Crescent, Simcoe, ON , MLS #N13226498 , Image - 1

128 Copeland Crescent Cookstown, Innisfil, Simcoe, ON MLS® N13226498

Residential Freehold (Detached)

$2100000.0

4 Beds
5 Baths
3500-5000 sq-ft

Refined, spacious and filled w/ natural light, this exceptional North Star Homes Stagecoach model offers 5,184 sq ft of finished living space on a pre

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4421 5th Line N/A, Simcoe, ON , MLS #N13661380 , Image - 1

4421 5th Line N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13661380

Residential Freehold (Detached)

$2258888.0

4 Beds
3 Baths
3500-5000 sq-ft

Truly a one of a kind property - The Carswell House is a remarkable Georgian-style home with immense history and character. Built circa 1840's by one

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58 Sydenham Trail W, Simcoe, ON , MLS #S13700916 , Image - 1

58 Sydenham Trail W Rural Clearview, Clearview, Simcoe, ON MLS® S13700916

Residential Freehold (Detached)

$3425000.0

4 Beds
5 Baths
3500-5000 sq-ft

A remarkable fusion of architecture, landscape & modern European design, this nearly 4,100 sq. ft. Scottish Longhouse by Scot-Build Developments sits

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995611 Mono-Adjala Townline N/A, Simcoe, ON , MLS #N13675058 , Image - 1

995611 Mono-Adjala Townline N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13675058

Residential Freehold (Detached)

$6999000.0

5 +1 Beds
7 Baths
5000 + sq-ft

Set amid 97+ acres of rolling countryside, private forests, and spring-fed ponds, Pond Hill Farm is a rare legacy estate where true eco-conscious livi