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Simcoe, ON Luxury Homes

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

Last Updated: September 26, 2026

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243 Champlain Road, Simcoe, ON , MLS #S13669278 , Image - 1

243 Champlain Road Penetanguishene, Simcoe, ON MLS® S13669278

Residential Freehold (Detached)

$2399000.0

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

Exceptional custom-built, south facing energy-efficient bungalow on almost 3 private acres with an incredible 720 ft. of Georgian Bay peninsula, sandy

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6 Georgian Grande Drive, Simcoe, ON , MLS #S13786564 , Image - 1

6 Georgian Grande Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13786564

Residential Freehold (Detached)

$2250000.0

4 +1 Beds
6 Baths
2500-3000 sq-ft

6 Georgian Grande Drive is truly a one-of-a-kind home in the sought-after Braestone lifestyle community. Renovated with an exceptional level of care a

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4 Walter James Parkway, Simcoe, ON , MLS #S13831740 , Image - 1

4 Walter James Parkway Snow Valley, Springwater, Simcoe, ON MLS® S13831740

Residential Freehold (Detached)

$2549900.0

4 +1 Beds
6 Baths
2500-3000 sq-ft

Welcome to 4 Walter James Parkway. Located in the sought after Cameron Estates pocket of Snow Valley, this custom executive bungalow with loft sits on

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

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247 Lakeshore Road W, Simcoe, ON , MLS #S13829078 , Image - 1

247 Lakeshore Road W Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13829078

Residential Freehold (Detached)

$5999500.0

4 Beds
5 Baths
3500-5000 sq-ft

If Lake Simcoe had a front row, this would be it. Set on 1.09 private acres along Lake Simcoe's prestigious North Shore, 247 Lakeshore Rd West pairs 9

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

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102 Pine Hill Road, Simcoe, ON , MLS #N13830862 , Image - 1

102 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13830862

Residential Freehold (Detached)

$2649000.0

4 +2 Beds
6 Baths
3500-5000 sq-ft

Set Within The Prestigious Shires Estates Community, This Impressive All-Brick Country Residence Is Surrounded By 2.33 Acres Of Scenic Privacy With Ma

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6591 6th Line, Simcoe, ON , MLS #N13829842 , Image - 1

6591 6th Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13829842

Residential Freehold (Detached)

$2999000.0

5 +1 Beds
6 Baths
3500-5000 sq-ft

Welcome to an exceptionally rare 10-acre country retreat with impressive wide frontage, ideally located just north of King. Offering the perfect combi

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3591 Line 12 N/A, Simcoe, ON , MLS #N13089012 , Image - 1

3591 Line 12 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13089012

Residential Freehold (Farm)

$2350000.0

Price drop by 21.6%

3 Beds
2 Baths
2000-2500 sq-ft

Rare Opportunity To Own An Extraordinary 26+ Acre Horse Farm Featuring Two Fully Independent Residences In Highly Desirable Bradford West Gwillimbury.

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529 Saint Marie Street, Simcoe, ON , MLS #S13827574 , Image - 1

529 Saint Marie Street Collingwood, Simcoe, ON MLS® S13827574

Residential Freehold (Detached)

$2475000.0

5 Beds
4 Baths
3500-5000 sq-ft

Welcome To 529 Ste Marie Street, An Opulent, Red-Brick Century Masterpiece On One Of Collingwood's Most Coveted Mature Tree Lined Streets. Just Steps

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4 Morrison Court, Simcoe, ON , MLS #N13794188 , Image - 1

4 Morrison Court Rural Essa, Essa, Simcoe, ON MLS® N13794188

Residential Freehold (Detached)

$2098000.0

4 Beds
4 Baths
3500-5000 sq-ft

Set on a private 1.56-acre lot at the end of a quiet cul-de-sac in Ridge Hill Estates, this executive 2-storey home offers open country views and a ba

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

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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

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

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

Residential Freehold (Detached)

$2450000.0

Price drop by 10.9%

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

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13 Parkland Drive, Simcoe, ON , MLS #S12979534 , Image - 1

13 Parkland Drive Rural Clearview, Clearview, Simcoe, ON MLS® S12979534

Residential Freehold (Detached)

$2250000.0

4 Beds
4 Baths
2500-3000 sq-ft

Your Dream Home Awaits in Prestigious Collingwoodlands. Discover the essence of refined country living in this truly exquisite 4-bedroom custom-built

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209 Bay Street, Simcoe, ON , MLS #S13508726 , Image - 1

209 Bay Street Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13508726

Residential Freehold (Detached)

$4490000.0

5 Beds
5 Baths
3000-3500 sq-ft

Rare Waterfront Estate in Prestigious Shanty BayA rare opportunity to own an exceptional waterfront retreat in the heart of Shanty Bay. Tucked away on

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1304 Bass Lake Side Road N/A W, Simcoe, ON , MLS #S13677378 , Image - 1

1304 Bass Lake Side Road N/A W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13677378

Residential Freehold (Detached)

$2295000.0

5 Beds
5 Baths
2500-3000 sq-ft

Few properties do this much. On 20 acres in Oro-Medonte, this one is a family home, a hobby farm, a workshop and a four-season basecamp at once. The f

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668 Florence Road, Simcoe, ON , MLS #N13822110 , Image - 1

668 Florence Road Alcona, Innisfil, Simcoe, ON MLS® N13822110

Residential Freehold (Detached)

$2148000.0

5 Beds
5 Baths
3500-5000 sq-ft

Why escape to the cottage on weekends when you can live the lifestyle every day? Welcome to this spectacular custom-built luxury home, completed in 20

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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

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58 White Oaks Road, Simcoe, ON , MLS #S13708164 , Image - 1

58 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S13708164

Residential Freehold (Detached)

$2075000.0

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to a truly one of a kind opportunity to own a prime piece of waterfront real estate nestled along the sandy shores of Kempenfelt Bay. This lar

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4767 14th Line, Simcoe, ON , MLS #N13819412 , Image - 1

4767 14th Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13819412

Residential Freehold (Detached)

$2100000.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

A four-season cottage without the cottage. 4,300+ sq ft of finished living space and 8 walkouts on 1.57 private acres backing onto a tree-lined stream

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3869 7th Line, Simcoe, ON , MLS #N13638014 , Image - 1

3869 7th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N13638014

Residential Freehold (Farm)

$3400000.0

4 Beds
3 Baths
2500-3000 sq-ft

Prime 78.8-acre agricultural property on paved 7th Line, Innisfil, ideally located between the Village of Thornton and the rapidly growing Innisfil Be

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6952 Second Line N/A, Simcoe, ON , MLS #N13819376 , Image - 1

6952 Second Line N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13819376

Residential Freehold (Detached)

$3999000.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

171-acre country property with main house and newly created 2-storey apartment in the newly restored century barn. Turnkey country property. Bring you

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11 Byers Street, Simcoe, ON , MLS #S13756856 , Image - 1

11 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S13756856

Residential Freehold (Detached)

$2399900.0

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

Nestled on a premium lot in prestigious Cameron Estates, this exceptional executive bungalow offers a rare blend of luxury, privacy and resort-inspire

Open House : Sun Sep 27, 12:00 PM to 02:00 PM

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2014 Innisbrook Street, Simcoe, ON , MLS #N13795392 , Image - 1

2014 Innisbrook Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13795392

Residential Freehold (Detached)

$2398000.0

Price drop by 2.0%

5 +1 Beds
5 Baths
3500-5000 sq-ft

Location, Location & Location! Welcome To 2014 Innisbrook Street! This Luxurious Custom-Built 2-Storey Residence Offers An Exceptional Lifestyle On Al

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8672 County Rd 91 Road, Simcoe, ON , MLS #S13736848 , Image - 1

8672 County Rd 91 Road Rural Clearview, Clearview, Simcoe, ON MLS® S13736848

Residential Freehold (Detached)

$2875000.0

5 Beds
4 Baths
2000-2500 sq-ft

Luxury Estate where timeless craftsmanship meets modern elegance. Nestled on over 4 acres of picturesque countryside, this custom-built 5-bedroom, 4-b

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130 Melissa Lane, Simcoe, ON , MLS #S12747348 , Image - 1

130 Melissa Lane Rural Tiny, Tiny, Simcoe, ON MLS® S12747348

Residential Freehold (Detached)

$3299000.0

Price drop by 2.7%

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

Nestled within the exclusive Cedar Ridge community in Tiny Township, this architect-designed retreat offers a rare opportunity to own a custom waterfr

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339 Champlain Road, Simcoe, ON , MLS #S13732230 , Image - 1

339 Champlain Road Penetanguishene, Simcoe, ON MLS® S13732230

Residential Freehold (Detached)

$3450000.0

3 Beds
4 Baths
3500-5000 sq-ft

This is one of a kind! Some properties simply exist in a category of their own. This extraordinary waterfront estate along the shores of Georgian Bay

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40 South Island Trail, Simcoe, ON , MLS #S13564130 , Image - 1

40 South Island Trail Rural Ramara, Ramara, Simcoe, ON MLS® S13564130

Residential Freehold (Detached)

$2290000.0

4 Beds
5 Baths
3500-5000 sq-ft

Experience Extraordinary Waterfront Living in this One-Of-A-Kind Custom Estate, Where Timeless Craftsmanship meets Today's Luxury Lifestyle. Designed

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359-363 Duckworth Street, Simcoe, ON , MLS #S13584928 , Image - 1

359-363 Duckworth Street Grove East, Barrie, Simcoe, ON MLS® S13584928

Residential Freehold (Other)

$12350000.0

Price drop by 5.0%

99 +45 Beds
64 Baths
5000 + sq-ft

Rare student housing investment opportunity in Barrie, offering immediate cash flow. This offering includes two well-maintained, purpose-built apartme

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2623 Con 10 N Nottawasaga Side Road N, Simcoe, ON , MLS #S13812540 , Image - 1

2623 Con 10 N Nottawasaga Side Road N Rural Clearview, Clearview, Simcoe, ON MLS® S13812540

Residential Freehold (Rural Residential)

$3395000.0

3 +3 Beds
4 Baths
3500-5000 sq-ft

Set across 95 acres with commanding views directly toward the ski hills of Osler Bluff, this landmark country estate offers a remarkable combination o

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