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Collingwood, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Collingwood. 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 Collingwood

Last Updated: September 23, 2026

29 Photos

4 Buckingham Boulevard, Simcoe, ON , MLS #S13814476 , Image - 1

4 Buckingham Boulevard Collingwood, Simcoe, ON MLS® S13814476

Residential Freehold (Detached)

$2799000.0

7 Beds
4 Baths
3500-5000 sq-ft

Experience unparalleled luxury and exceptional investment potential at 4 Buckingham Boulevard, an expansive estate offering over 5,000 sq. ft. of exqu

47 Photos

291 Third Street, Simcoe, ON , MLS #S13811550 , Image - 1

291 Third Street Collingwood, Simcoe, ON MLS® S13811550

Residential Freehold (Detached)

$2499000.0

5 Beds
3 Baths
3000-3500 sq-ft

**A Rare Collingwood Masterpiece - Historic Character, Modern Luxury & Unparalleled Potential!** This extraordinary 1894 red brick estate is set on a

46 Photos

98 Huron Street, Simcoe, ON , MLS #S13754592 , Image - 1

98 Huron Street Collingwood, Simcoe, ON MLS® S13754592

Residential Freehold (Detached)

$2449000.0

4 +2 Beds
4 Baths
3000-3500 sq-ft

COVETED SUNSET POINT LOCATION!! Welcome to an exceptional custom-built residence where timeless Victorian-inspired elegance meets the beauty of Georgi

32 Photos

7 Meadowlark Way, Simcoe, ON , MLS #S13726820 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S13726820

Residential Freehold (Detached)

$3500000.0

3 +2 Beds
4 Baths
2500-3000 sq-ft

A CONTEMPORARY ESTATE DESIGNED FOR ELEVATED FOUR-SEASON LIVING! Set on 1.21 acres in Windrose Estates, an estate enclave of custom homes on large prop

Open House : Sat Sep 26, 12:00 PM to 02:00 PM

50 Photos

63 Georgian Manor Drive, Simcoe, ON , MLS #S13658890 , Image - 1

63 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S13658890

Residential Freehold (Detached)

$2695000.0

Price drop by 2.0%

5 Beds
3 Baths
3000-3500 sq-ft

Wake up to spectacular sunrises, unwind with unforgettable sunsets, and enjoy panoramic 180-degree views across Nottawasaga Bay from this exceptional

45 Photos

12 WHEELHOUSE Crescent, Simcoe, ON , MLS #S13735694 , Image - 1

12 WHEELHOUSE Crescent Collingwood, Simcoe, ON MLS® S13735694

Residential Condo & Other (Condo Townhouse)

$2300000.0

4 +0 Beds
4 Baths
2750-2999 sq-ft

This spectacular waterfront condo in The Shipyards offers 3,591 square feet of finished living space across three storeys of luxury construction, with

47 Photos

222 Oak Street, Simcoe, ON , MLS #S13701580 , Image - 1

222 Oak Street Collingwood, Simcoe, ON MLS® S13701580

Residential Freehold (Detached)

$2950000.0

5 Beds
4 Baths
3500-5000 sq-ft

Welcome to 222 Oak Street, where timeless elegance meets modern luxury in this custom-built North Oak home. Set on a fenced full town lot in downtown

40 Photos

6920 Poplar Side Road, Simcoe, ON , MLS #S13602452 , Image - 1

6920 Poplar Side Road Collingwood, Simcoe, ON MLS® S13602452

Residential Freehold (Detached)

$2399900.0

4 Beds
4 Baths
3000-3500 sq-ft

Welcome to 6920 Poplar Side Road, a stunning custom-built estate on nearly 1.8 acres in Collingwood. Offering 3430 sqft above grade plus an unfinished

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Collingwood, ON Luxury Homes

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