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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 20, 2025

11 Photos

3568 4 Line, Simcoe, ON , MLS #N12641382 , Image - 1

3568 4 Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12641382

Residential Freehold (Vacant Land)

$3500000.0

Are you ready to turn your real estate dreams into reality? Presenting a golden opportunity for savvy investors - a sprawling piece of vacant land nes

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8464 6th Line, Simcoe, ON , MLS #N12638712 , Image - 1

8464 6th Line Rural Essa, Essa, Simcoe, ON MLS® N12638712

Residential Freehold (Detached)

$2500000.0

4 Beds
3 Baths
3500-5000 sq-ft

TIMBER-FRAME ESTATE ON 10 ACRES WITH INGROUND POOL, EXPANSIVE BARN, VERSATILE OUTBUILDINGS, & A 4,544 SQ FT HOME BUILT TO IMPRESS! Call it a farmhouse

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7 Meadowlark Way, Simcoe, ON , MLS #S12639170 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S12639170

Residential Freehold (Detached)

$3590000.0

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

MODERN, ORGANIC & TIMELESS CUSTOM-BUILT BUNGALOW FEATURING OVER 5,500 SQFT OF COMFORT-DRIVEN LIVING SPACE! Located in the equally coveted and conveni

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6409 10th Line, Simcoe, ON , MLS #N12638922 , Image - 1

6409 10th Line Rural Essa, Essa, Simcoe, ON MLS® N12638922

Residential Freehold (Farm)

$3150000.0

3 Beds
2 Baths
1500-2000 sq-ft

100 acre Farm for sale / 80 acres of workable land. Cash crop and livestock opportunities. Nicely maintained 4 bedroom, 2 bathroom farmhouse. Huge kit

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

40 Photos

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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1372 Division Road E, Simcoe, ON , MLS #S12517032 , Image - 1

1372 Division Road E Rural Severn, Severn, Simcoe, ON MLS® S12517032

Residential Freehold (Detached)

$2199000.0

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

INDULGE IN LUXURY ON 2.1 ACRES WITH BREATHTAKING VIEWS, SHARED OWNERSHIP OF AN ADDITIONAL 32 ACRES, & A MAN-MADE LAKE!! Enter a realm of unrivalled el

25 Photos

7475 Poplar Side Road, Simcoe, ON , MLS #S12383439 , Image - 1

7475 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12383439

Residential Freehold (Vacant Land)

$7500000.0

1 Baths
1100-1500 sq-ft

Future Development Opportunity on 84.6 acres on Poplar Sideroad with the Pretty River flowing through the land and abutting the Train Trail. A very bu

42 Photos

8485 Highway 93 N/A, Simcoe, ON , MLS #S12558060 , Image - 1

8485 Highway 93 N/A Rural Tiny, Tiny, Simcoe, ON MLS® S12558060

Residential Freehold (Farm)

$2170000.0

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

Top 5 Reasons You Will Love This Home: 1) Nearly 80-acres of income-producing land offering multiple revenue streams, including income from barn signa

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7833 Poplar Side Road, Simcoe, ON , MLS #S12475972 , Image - 1

7833 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12475972

Residential Freehold (Detached)

$3100000.0

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

Welcome to an extraordinary 14.95-acre country estate that defines luxury living in the heart of Collingwood. Just minutes from downtown yet surrounde

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7 Purple Hill Lane, Simcoe, ON , MLS #S12405373 , Image - 1

7 Purple Hill Lane Creemore, Clearview, Simcoe, ON MLS® S12405373

Residential Freehold (Detached)

$2190000.0

5 +1 Beds
4 Baths
2500-3000 sq-ft

Discover your own private retreat in this 4,297 sqft resort-style home set on 1.84 acres of beautifully landscaped grounds. With a 3-car garage, 12 pe

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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

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

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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

45 Photos

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

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

41 Photos

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

44 Photos

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

39 Photos

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

50 Photos

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

40 Photos

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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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

17 Photos

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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