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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: August 13, 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 +2 Beds
4 Baths
2000-2500 sq-ft

Exceptional custom-built, energy-efficient bungalow on almost 3 private acres with an incredible 700 ft. of Georgian Bay shoreline, sandy beach areas

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156 Bartlett Boulevard, Simcoe, ON , MLS #S12794486 , Image - 1

156 Bartlett Boulevard Collingwood, Simcoe, ON MLS® S12794486

Residential Freehold (Detached)

$3950000.0

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

Welcome to your dream waterfront oasis in Collingwood, Ontario. This stunning home offers the rare luxury of docking your boat right at your property,

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180 Courtland Street, Simcoe, ON , MLS #S13667800 , Image - 1

180 Courtland Street Atherley, Ramara, Simcoe, ON MLS® S13667800

Residential Freehold (Farm)

$4999000.0

4 Beds
3 Baths
2500-3000 sq-ft

A truly remarkable 102 acre offering combining country living, extensive equestrian facilities, multiple residences, significant income generation and

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1068 Shore Lane, Simcoe, ON , MLS #S13667500 , Image - 1

1068 Shore Lane Wasaga Beach, Simcoe, ON MLS® S13667500

Residential Freehold (Detached)

$2599900.0

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

Welcome to waterfront living at its finest! This exceptional 2+2 bedroom bungaloft offers an incredible blend of comfort, functionality & breathtaking

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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245 Pine Hill Road, Simcoe, ON , MLS #N13615814 , Image - 1

245 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13615814

Residential Freehold (Detached)

$2480000.0

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

A rare opportunity to own a luxury estate on one of Bradford's most desirable executive streets. Situated on a premium 1.66-acre pie-shaped lot, this

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521 huronia Road, Simcoe, ON , MLS #S13666922 , Image - 1

521 huronia Road Painswick South, Barrie, Simcoe, ON MLS® S13666922

Residential Freehold (Vacant Land)

$3120000.0

Exceptional development opportunity at 521 Huronia Road in Barrie. This approximately 15.5-acre property offers significant development potential in a

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102 Pine Hill Road, Simcoe, ON , MLS #N13427258 , Image - 1

102 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13427258

Residential Freehold (Detached)

$2689000.0

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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17 Cherry Street, Simcoe, ON , MLS #S13513284 , Image - 1

17 Cherry Street Collingwood, Simcoe, ON MLS® S13513284

Residential Freehold (Detached)

$2199000.0

Price drop by 4.4%

3 +2 Beds
4 Baths
1500-2000 sq-ft

Rare opportunity to own a truly one-of-a-kind Georgian Bay waterfront property in Collingwood. Tucked away at the end of a quiet dead-end street, this

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2 Dale Crescent, Simcoe, ON , MLS #N13596444 , Image - 1

2 Dale Crescent Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13596444

Residential Freehold (Detached)

$2199999.0

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

A Custom-Built Bungalow On 1 Acre, Complete With A Heated Saltwater Pool, Over 3,000 Sq Ft Of Main-Floor Living, And A Finished Basement With Two Stai

Open House : Sun Aug 16, 01:00 PM to 03:00 PM

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2055 Forest Valley Drive, Simcoe, ON , MLS #N13662834 , Image - 1

2055 Forest Valley Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13662834

Residential Freehold (Detached)

$2239000.0

3 +1 Beds
4 Baths
2500-3000 sq-ft

MULTI-GENERATIONAL LIVING AT ITS FINEST. Set on 1.27 Acres with Lovers Creek tracing the edge of the property, this custom-built 3+1 bedroom home beau

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39 Plunkett Court, Simcoe, ON , MLS #S13215634 , Image - 1

39 Plunkett Court Bayshore, Barrie, Simcoe, ON MLS® S13215634

Residential Freehold (Detached)

$4998000.0

Price drop by 4.8%

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

Welcome To 39 Plunkett Court, An Extraordinary Custom-Built Waterfront Estate Offering 99' Of Frontage On Kempenfelt Bay In Barrie's Prestigious Tolle

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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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5097 Conc Rd 2 Concession Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12855646

Residential Freehold (Vacant Land)

$3249999.0

Price drop by 7.1%

Calling all Cash Crop Farmers regarding a rare agricultural offering at 5097 Concession Rd 2, Everett .This 212-acre parcel is a rare find, and an app

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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)

$2750000.0

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

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2014 Innisbrook Street, Simcoe, ON , MLS #N13628432 , Image - 1

2014 Innisbrook Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13628432

Residential Freehold (Detached)

$2600000.0

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

Welcome To 2014 Innisbrook! This Luxurious Custom Built 2 Storey Home Provides You The Lifestyle Many Can Just Dream Of. Over 7250 Sq Ft Living Space,

Open House : Sat Aug 15, 01:00 PM to 03:00 PM

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10258 Highway 9 N/A E, Simcoe, ON , MLS #N12834076 , Image - 1

10258 Highway 9 N/A E Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12834076

Residential Freehold (Detached)

$5900000.0

4 Beds
3 Baths
2500-3000 sq-ft

10258 Highway 9 presents a rare opportunity to own an extraordinary 91-acre corner estate in Ontario's highly desirable rural landscape, bordering Cal

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7583 Oak Point Road, Simcoe, ON , MLS #S13546682 , Image - 1

7583 Oak Point Road Rural Ramara, Ramara, Simcoe, ON MLS® S13546682

Residential Freehold (Detached)

$2595000.0

Price drop by 3.7%

6 Beds
3 Baths
3500-5000 sq-ft

DECOMMISSIONED Train Bridge! $100k in Recent Upgrades - All New Modern Windows & Front Door. Welcome to Oak Point Estate - featured on Lakefront Luxur

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2623 Con 10 N Nottawasaga Side Road N, Simcoe, ON , MLS #S13572766 , Image - 1

2623 Con 10 N Nottawasaga Side Road N Rural Clearview, Clearview, Simcoe, ON MLS® S13572766

Residential Freehold (Rural Residential)

$3900000.0

Price drop by 13.3%

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

Capturing every changing views of the Niagara Escarpment from 95 breathtaking acres, this extraordinary country estate offers a rare opportunity to em

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44-46 Gray Lane, Simcoe, ON , MLS #S13652280 , Image - 1

44-46 Gray Lane Innis-Shore, Barrie, Simcoe, ON MLS® S13652280

Residential Freehold (Detached)

$6399000.0

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

Discover one of Barrie's most exceptional waterfront estates on the shores of Lake Simcoe. Set on just under an acre, this custom-built luxury residen

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13 Georgina Drive S, Simcoe, ON , MLS #S13626724 , Image - 1

13 Georgina Drive S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13626724

Residential Freehold (Detached)

$3149000.0

3 Beds
4 Baths
2000-2500 sq-ft

Truly an extraordinary waterfront opportunity on the coveted North Shore of Kempenfelt Bay! This is a unique opportunity to secure 120 feet of pristi

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98 Huron Street, Simcoe, ON , MLS #S13249778 , Image - 1

98 Huron Street Collingwood, Simcoe, ON MLS® S13249778

Residential Freehold (Detached)

$2499000.0

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

Victorian Elegance Meets Georgian Bay Waterfront Living! Breathtaking custom-built home overlooking Sunset Point and the sparkling waters of Georgian

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2620 Baguley Road W, Simcoe, ON , MLS #S13649408 , Image - 1

2620 Baguley Road W Port Severn, Severn, Simcoe, ON MLS® S13649408

Residential Freehold (Detached)

$2575000.0

5 Beds
3 Baths
2000-2500 sq-ft

Discover year-round waterfront living on beautiful Little Lake with 319.07 feet of straight-line frontage, expanding to 436 feet along the shoreline.

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8485 Highway 93 N/A, Simcoe, ON , MLS #S13580248 , Image - 1

8485 Highway 93 N/A Rural Tiny, Tiny, Simcoe, ON MLS® S13580248

Residential Freehold (Farm)

$2170000.0

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

Top 5 Reasons You Will Love This Home: 1) Expansive 80-acre rural estate delivering exceptional income potential with diversified revenue streams, inc

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130 Concession 15 N/A W, Simcoe, ON , MLS #S13576824 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S13576824

Residential Freehold (Detached)

$2499900.0

4 Beds
3 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Escape the limitations of the city with this 40-acre private compound in Tiny, offering a scale of infrastru

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1450 Line 3 N/A N, Simcoe, ON , MLS #S13566402 , Image - 1

1450 Line 3 N/A N Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13566402

Residential Freehold (Detached)

$3699999.0

3 +3 Beds
5 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Set on 48 breathtaking acres in the highly sought-after Oro-Medonte, this exceptional custom-built ICF home

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2265 Concession 11 Nottawasaga N/A S, Simcoe, ON , MLS #S13560428 , Image - 1

2265 Concession 11 Nottawasaga N/A S Rural Clearview, Clearview, Simcoe, ON MLS® S13560428

Residential Freehold (Detached)

$2399000.0

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

SOPHISTICATED COUNTRY LIVING IN A CUSTOM HOME IN SOUGHT-AFTER LOCATION ON SPRAWLING ACREAGE WITH A SEPARATE DETACHED SHOP, & A 2-BEDROOM INDEPENDENT S

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731 Concession 15 N/A W, Simcoe, ON , MLS #S13502250 , Image - 1

731 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S13502250

Residential Freehold (Detached)

$3950000.0

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

A rare offering on the shores of Georgian Bay in Tiny Township, this extraordinary waterfront estate redefines luxury living with an unmatched blend o

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3554 Concession 3 N/A, Simcoe, ON , MLS #S13462930 , Image - 1

3554 Concession 3 N/A Rural Clearview, Clearview, Simcoe, ON MLS® S13462930

Residential Freehold (Rural Residential)

$6690000.0

6 Beds
5 Baths
3500-5000 sq-ft

Welcome to Fairview Farm, a remarkable 57-acre country estate just minutes from Creemore, where history, natural beauty and an exceptional lifestyle c

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2353 County Road 124 N/A, Simcoe, ON , MLS #S13169688 , Image - 1

2353 County Road 124 N/A Rural Clearview, Clearview, Simcoe, ON MLS® S13169688

Residential Freehold (Detached)

$8950000.0

3 +1 Beds
5 Baths
3500-5000 sq-ft

TALLY HO! A LANDMARK ESTATE RICH IN HISTORY - Once a bustling stagecoach stop in the 1850s, Tally Ho has evolved over the past 30 years into one of th

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10195 Highway 12 N/A W, Simcoe, ON , MLS #S13155114 , Image - 1

10195 Highway 12 N/A W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13155114

Residential Freehold (Farm)

$2299900.0

3 Beds
3 Baths
3000-3500 sq-ft

A TRUE LIVE-WORK PROPERTY WITH A RETAIL STORE, OFFICE, MULTIPLE OUTBUILDINGS & OVER 95 ACRES TO GROW YOUR VISION! This picture-worthy property offers

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