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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: December 12, 2025

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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

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3777 Ferretti Court, Simcoe, ON , MLS #N12224377 , Image - 1

3777 Ferretti Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N12224377

Residential Freehold (Att/Row/Townhouse)

$2212990.0

3 Beds
4 Baths
2500-3000 sq-ft

Brand New 3-Storey Townhome at Friday Harbour Resort. This Stunning 3 Bedroom waterfront home is the epitome of low maintenance, all season lakeside

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24 Finley Drive, Simcoe, ON , MLS #S12474342 , Image - 1

24 Finley Drive Rural Tiny, Tiny, Simcoe, ON MLS® S12474342

Residential Freehold (Detached)

$2699000.0

2 +3 Beds
4 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Custom waterfront home featuring 4,066 square feet above ground and 5,899 total, while being nestled on a do

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95 lakeshore Road E, Simcoe, ON , MLS #S12475807 , Image - 1

95 lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12475807

Residential Freehold (Detached)

$2150000.0

Price drop by 4.4%

3 +1 Beds
3 Baths
1500-2000 sq-ft

Don't be deceived by this home's modest roadside appearance-behind the front door awaits a private lakeside retreat offering over 2,700 sq. ft. of ren

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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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

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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

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1359 Old Barrie Road E, Simcoe, ON , MLS #S12446590 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S12446590

Residential Freehold (Detached)

$2299900.0

4 +1 Beds
5 Baths
3000-3500 sq-ft

Highest Quality From Top To Bottom Over 5000SqFt Of Available Living Space, South Western Exposure Backyard. One Of A Kind It Factor Family Home on 37

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150 Essa Road, Simcoe, ON , MLS #S12609246 , Image - 1

150 Essa Road Allandale, Barrie, Simcoe, ON MLS® S12609246

Residential Freehold (Detached)

$2700000.0

3 Beds
4 Baths
1500-2000 sq-ft

Development Opportunity for up to 12 story -120 unit residential building or possible commercial building. Prime corner location. Re-zoned urban trans

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0000 POOLTON Lane, Simcoe, ON , MLS #S12609416 , Image - 1

0000 POOLTON Lane Painswick North, Barrie, Simcoe, ON MLS® S12609416

Residential Freehold (Vacant Land)

$7999999.0

Vacant land with Development Opportunity. Prime location. Potential of 55-60 townhomes. Property currently is Registered plan of subdivision zoned for

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4065 15th Line, Simcoe, ON , MLS #N12498630 , Image - 1

4065 15th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N12498630

Residential Freehold (Farm)

$5499000.0

1 Baths
< 700 sq-ft

Top 5 Reasons You Will Love This Property: 1) Exceptional land banking and future development opportunity with 137.5-acres of prime land adjacent to d

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3870 Darling Island Road, Simcoe, ON , MLS #S12352866 , Image - 1

3870 Darling Island Road Port Severn, Severn, Simcoe, ON MLS® S12352866

Residential Freehold (Detached)

$2299900.0

3 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Constructed with state-of-the-art BONE Structure technology boasting a steel and concrete frame for unmatche

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18 Edgewater Road, Simcoe, ON , MLS #S12400170 , Image - 1

18 Edgewater Road Wasaga Beach, Simcoe, ON MLS® S12400170

Residential Freehold (Detached)

$2999000.0

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

Sitting majestically on one of the most spectacular riverfront lots on the Nottawasaga River in beautiful Wasaga Beach you will find this newly built

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2249 PILKINGTON Lane, Simcoe, ON , MLS #S12236910 , Image - 1

2249 PILKINGTON Lane Rural Severn, Severn, Simcoe, ON MLS® S12236910

Residential Freehold (Detached)

$6780000.0

8 +1 Beds
10 Baths
5000 + sq-ft

Welcome to the crown jewel of Ontario's world-renowned cottage country an exquisite combination of 10,000+ sq. ft. custom-built estate retreat perche

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138 Knox Road E, Simcoe, ON , MLS #S12437128 , Image - 1

138 Knox Road E Wasaga Beach, Simcoe, ON MLS® S12437128

Residential Freehold (Detached)

$2149000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) A rare 5.6-acre setting surrounded by trees and nature, while being just steps to the Nottawasaga River and

33 Photos

331 Tornado Drive, Simcoe, ON , MLS #N12106179 , Image - 1

331 Tornado Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12106179

Residential Freehold (Farm)

$2900000.0

Price drop by 3.3%

3 +1 Beds
1 Baths
1100-1500 sq-ft

Welcome to 331 Tornado Dr, Nestled in the Quiet Farming Community of Bradford West Gwillimbury. This residential farmland is a terrific opportunity fo

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57 Glenhuron Drive, Simcoe, ON , MLS #S12597102 , Image - 1

57 Glenhuron Drive Midhurst, Springwater, Simcoe, ON MLS® S12597102

Residential Freehold (Detached)

$4195000.0

4 +2 Beds
6 Baths
5000 + sq-ft

Brand new, jaw dropping custom estate located just steps to Barrie in ultra desirable Midhurst. No expense spared with over 10,000 square feet of fini

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1536 Tiny Beaches Road N, Simcoe, ON , MLS #S11896365 , Image - 1

1536 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S11896365

Residential Freehold (Detached)

$3399000.0

4 Beds
1 Baths
700-1100 sq-ft

For more information, please click Brochure button. Your opportunity to own an awesome four season waterfront beach house with 102 feet of sandy shore

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4 Meadowlark Way, Simcoe, ON , MLS #S12398226 , Image - 1

4 Meadowlark Way Rural Clearview, Clearview, Simcoe, ON MLS® S12398226

Residential Freehold (Detached)

$2995000.0

5 Beds
6 Baths
3500-5000 sq-ft

This is it! Get settled before ski season. Welcome to 4 Meadowlark Way, a rare offering in one of the area's most exclusive communities of just 44 est

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3328 4 Line N, Simcoe, ON , MLS #S12399041 , Image - 1

3328 4 Line N Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12399041

Residential Freehold (Detached)

$2495000.0

Price drop by 3.9%

4 +1 Beds
3 Baths
3000-3500 sq-ft

Wow! Welcome to *** 3328 4 Line N *** Prestigious horseshoe valley opportunity! Fabulous custom detached two story in the luxury residential area loca

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1910 18th Sideroad N/A, Simcoe, ON , MLS #N12478512 , Image - 1

1910 18th Sideroad N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12478512

Residential Freehold (Detached)

$2490000.0

Price drop by 4.2%

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

Willow Ridge Farm, Schomberg Heights; Exclusive 5 acre, luxury custom built ranch bungalow, over 5,000 sq. ft. of comfortable living space with 4 bedr

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1052 Sideroad 20 N/A, Simcoe, ON , MLS #N12550398 , Image - 1

1052 Sideroad 20 N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12550398

Residential Freehold (Vacant Land)

$3895000.0

This spectacular estate lot immediately outside of highly desirable village of Schomberg is a once in a lifetime opportunity. The 157 acres of rolling

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4 BUCKINGHAM Boulevard, Simcoe, ON , MLS #S12211234 , Image - 1

4 BUCKINGHAM Boulevard Collingwood, Simcoe, ON MLS® S12211234

Residential Freehold (Detached)

$2999990.0

Price drop by 1.6%

7 Beds
4 Baths
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

39 Photos

2981 Ninth Line, Simcoe, ON , MLS #N12474079 , Image - 1

2981 Ninth Line Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12474079

Residential Freehold (Detached)

$2380800.0

Price drop by 4.3%

5 +2 Beds
5 Baths
2500-3000 sq-ft

Welcome To 2981 Ninth Line, An Impressive Custom-Built Executive Home W/ Breathtaking Panoramic Views Of Nature's Finest Beauty. Truly A Dream Home In

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7369 5th Side Road, Simcoe, ON , MLS #N12070247 , Image - 1

7369 5th Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12070247

Residential Freehold (Farm)

$2875000.0

Price drop by 17.7%

5 Beds
3 Baths
2500-3000 sq-ft

This property offers a prime location, immediately abutting the border of New Tecumseth, with two road frontages for easy access. The 2610 sq.ft. farm

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215 Dock Road, Simcoe, ON , MLS #S12535710 , Image - 1

215 Dock Road South Shore, Barrie, Simcoe, ON MLS® S12535710

Residential Freehold (Detached)

$2995000.0

Price drop by 3.1%

4 +1 Beds
5 Baths
5000 + sq-ft

Welcome to your dream home, just steps from Kempenfelt Bay! This exceptional 4+1 bedroom detached home is nestled in one of Barrie's most exclusive ar

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6643 3rd Line, Simcoe, ON , MLS #N12562584 , Image - 1

6643 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12562584

Residential Freehold (Detached)

$2999000.0

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

This stunning 6-bedroom, 6-bathroom bungalow on 10 acres just north of King offers luxurious living with the convenience of nearby amenities. The prop

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58 White Oaks Road, Simcoe, ON , MLS #S12564712 , Image - 1

58 White Oaks Road South Shore, Barrie, Simcoe, ON MLS® S12564712

Residential Freehold (Detached)

$2149000.0

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

50 Photos

75 Indian Trail, Simcoe, ON , MLS #S12533084 , Image - 1

75 Indian Trail Collingwood, Simcoe, ON MLS® S12533084

Residential Freehold (Detached)

$2300000.0

6 Beds
4 Baths
3500-5000 sq-ft

This dream waterfront estate home could be yours for the 2025/2026 Ski season. Spanning nearly 5,000 square feet of living space, this six-bedroom hom

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3965 Algoma Avenue, Simcoe, ON , MLS #N12198631 , Image - 1

3965 Algoma Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12198631

Residential Freehold (Detached)

$2749999.0

Price drop by 31.0%

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

Luxury Custom Home Big Bay Point, Steps from Lake Simcoe! Welcome to this newly upgraded, move-in ready luxury bungaloft situated on a sprawling 200x

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2991 Concession Rd 4 N/A N, Simcoe, ON , MLS #N11896046 , Image - 1

2991 Concession Rd 4 N/A N Loretto, Adjala-Tosorontio, Simcoe, ON MLS® N11896046

Residential Freehold (Detached)

$4899000.0

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

NEW ESTATE HOME stunning 7,900 sq. ft. custom-built estate sprawls across over 10 acres of pristine land, offering the pinnacle of luxury living. With

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