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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: June 29, 2026

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11 Park Trail, Simcoe, ON , MLS #S12995010 , Image - 1

11 Park Trail Midhurst, Springwater, Simcoe, ON MLS® S12995010

Residential Freehold (Detached)

$2199800.0

5 Beds
5 Baths
3500-5000 sq-ft

Discover timeless elegance in this stunning English Tudor estate, perched on a private 2.2 acre lot in prestigious Midhurst. Thoughtfully positioned a

35 Photos

1614 Ridge Road E, Simcoe, ON , MLS #S6142920 , Image - 1

1614 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S6142920

Residential Freehold (Multiplex)

$3299000.0

Price drop by 1.8%

6 Beds
5 Baths
5000 + sq-ft

Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This U

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7874 10th Line, Simcoe, ON , MLS #N13492744 , Image - 1

7874 10th Line Rural Essa, Essa, Simcoe, ON MLS® N13492744

Residential Freehold (Farm)

$3699000.0

3 +0 Beds
2 Baths
1500-2000 sq-ft

Premium 106- Acre Country Estate & Farm Just West of Barrie. The Perfect blend of Modern Luxury, Fertile Land , and Investment Potential. Escape to th

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1000 Strawberry Island Rural Ramara, Ramara, Simcoe, ON MLS® S13130562

Residential Freehold (Other)

$3995000.0

< 700 sq-ft

A Truly Exceptional Fall And Winter Opportunity To Own Strawberry Island-A 26-Acre Private, Iconic, And Historically Significant Sanctuary On Lake Sim

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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00000 George Avenue Wasaga Beach, Simcoe, ON MLS® S13042710

Residential Freehold (Vacant Land)

$2350000.0

< 700 sq-ft

Attention Developers - 10.3 Acres Development Land. Zoned D for development. Non-residential Uses: Agricultural produce sales outlet, Agricultural use

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130 Concession 15 N/A W, Simcoe, ON , MLS #S12984964 , Image - 1

130 Concession 15 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S12984964

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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2698 Tottenham Road, Simcoe, ON , MLS #N13436382 , Image - 1

2698 Tottenham Road Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13436382

Residential Freehold (Detached)

$3250000.0

3 Beds
2 Baths
1500-2000 sq-ft

What truly sets this property apart is the impressive detached shop zone commercial with a front office, offering endless possibilities for business o

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183 Lakeshore Road W, Simcoe, ON , MLS #S13240562 , Image - 1

183 Lakeshore Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13240562

Residential Freehold (Detached)

$2950000.0

4 Beds
7 Baths
3500-5000 sq-ft

Welcome to this exceptional luxury waterfront estate on Lake Simcoe, offering over 97 feet of private shoreline in sought-after Oro-Medonte. Ideally l

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24 Finley Drive, Simcoe, ON , MLS #S13091062 , Image - 1

24 Finley Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13091062

Residential Freehold (Detached)

$2625000.0

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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153 Creighton Street S, Simcoe, ON , MLS #S13480050 , Image - 1

153 Creighton Street S Atherley, Ramara, Simcoe, ON MLS® S13480050

Residential Freehold (Detached)

$4899000.0

5 Beds
5 Baths
5000 + sq-ft

Curated with pure intention, exceptionally executed - here's a spectacular opportunity to own one of Lake Simcoe's most admirable waterfront estates!

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7369 5th Side Road, Simcoe, ON , MLS #N13467990 , Image - 1

7369 5th Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13467990

Residential Freehold (Rural Residential)

$2150000.0

5 Beds
4 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 2610sq.ft. farmh

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28 Alana Drive, Simcoe, ON , MLS #S13478104 , Image - 1

28 Alana Drive Centre Vespra, Springwater, Simcoe, ON MLS® S13478104

Residential Freehold (Detached)

$2099900.0

4 Beds
3 Baths
3500-5000 sq-ft

A private backyard retreat with a heated saltwater pool, multiple seating areas, and mature landscaping - ideal for relaxing, hosting friends, or spen

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767 Cedarvale Drive, Simcoe, ON , MLS #N12890686 , Image - 1

767 Cedarvale Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N12890686

Residential Freehold (Detached)

$2399999.0

4 Beds
4 Baths
3500-5000 sq-ft

Fabulous sun filled layout with a spectacular gourmet kitchen, with Thermador appliances. Family room with 32ft soaring cathedral ceilings. Custom lar

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114 Melissa Lane, Simcoe, ON , MLS #S13472210 , Image - 1

114 Melissa Lane Rural Tiny, Tiny, Simcoe, ON MLS® S13472210

Residential Freehold (Detached)

$5490000.0

8 Beds
8 Baths
3500-5000 sq-ft

Incomparable Private West Facing 2 Acres With 239 Ft. Of Water Frontage in One of the Finest Large Lot Communities in Southern Georgian Bay. Private S

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416 Bay Street, Simcoe, ON , MLS #S12978166 , Image - 1

416 Bay Street Orillia, Simcoe, ON MLS® S12978166

Residential Freehold (Detached)

$2498000.0

4 Beds
3 Baths
2500-3000 sq-ft

Tucked along the tranquil shoreline of Lake Couchiching, this cherished waterfront stylish residence tells a story nearly three decades in the making.

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1 PIERCE Court, Simcoe, ON , MLS #S13428306 , Image - 1

1 PIERCE Court Midhurst, Springwater, Simcoe, ON MLS® S13428306

Residential Freehold (Detached)

$2650000.0

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

Every once in a while, a property comes along that completely resets your expectations. Not because it sits on a breathtaking 4.33-acre estate lot. No

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95 Spruce Street, Simcoe, ON , MLS #S13452718 , Image - 1

95 Spruce Street Rural Tiny, Tiny, Simcoe, ON MLS® S13452718

Residential Freehold (Detached)

$3500000.0

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

Set on a beautifully private one-acre estate surrounded by mature forest, this exceptional custom-built 2023 residence offers a rare combination of mo

41 Photos

3965 Algoma Avenue, Simcoe, ON , MLS #N12937336 , Image - 1

3965 Algoma Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12937336

Residential Freehold (Detached)

$2499000.0

Price drop by 7.4%

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

Luxury Custom Bungaloft on Shoreline Road - Steps to Lake Simcoe! ****Welcome to this newly upgraded, move-in-ready custom bungaloft situated on a rar

48 Photos

1220 Shoreview Drive, Simcoe, ON , MLS #N13039442 , Image - 1

1220 Shoreview Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13039442

Residential Freehold (Detached)

$7250000.0

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

Welcome to this stunning luxury waterfront estate, a blend of elegant design, modern amenities, and breathtaking natural beauty. The exterior showcase

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3730 Mangusta Court, Simcoe, ON , MLS #N13439676 , Image - 1

3730 Mangusta Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13439676

Residential Freehold (Att/Row/Townhouse)

$2899999.0

5 Beds
5 Baths
3500-5000 sq-ft

Client RemarksRESORT LIVING AT ITS FINEST - Stunning 3550 Sqft Fully Upgraded End Unit Island Town On Prime Mangusta Court In The Sought After Marina

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6643 3rd Line, Simcoe, ON , MLS #N13242614 , Image - 1

6643 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13242614

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

49 Photos

8058 20th Side Road, Simcoe, ON , MLS #N13259422 , Image - 1

8058 20th Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13259422

Residential Freehold (Detached)

$2500000.0

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

The complete lifestyle for those who want more than a beautiful home - they want space, freedom, and a lifestyle that cannot be found in town. Set beh

47 Photos

202 Kempenfelt Drive, Simcoe, ON , MLS #S13425266 , Image - 1

202 Kempenfelt Drive North Shore, Barrie, Simcoe, ON MLS® S13425266

Residential Freehold (Detached)

$2099000.0

4 Beds
4 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Welcome to 202 Kempenfelt Drive, an extraordinary custom-built residence completed in 2020, ideally located

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359-363 Duckworth Street, Simcoe, ON , MLS #S13032490 , Image - 1

359-363 Duckworth Street Grove East, Barrie, Simcoe, ON MLS® S13032490

Residential Freehold (Other)

$13850000.0

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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6 Pinehurst Lane, Simcoe, ON , MLS #S13112938 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S13112938

Residential Freehold (Detached)

$2675000.0

Price drop by 0.9%

6 +3 Beds
6 Baths
5000 + sq-ft

Experience the ultimate retreat in this stunning custom-built estate, perfectly positioned on a private 1.62-acre lot just minutes from Barrie. Design

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376 Brewery Lane, Simcoe, ON , MLS #S13251518 , Image - 1

376 Brewery Lane Orillia, Simcoe, ON MLS® S13251518

Residential Freehold (Detached)

$4499999.0

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

Welcome to 376 Brewery Lane, a stunning luxury waterfront home situated on one of Orillias finest streets. This exceptional property offers 104 feet o

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57 Glenhuron Drive, Simcoe, ON , MLS #S13249574 , Image - 1

57 Glenhuron Drive Midhurst, Springwater, Simcoe, ON MLS® S13249574

Residential Freehold (Detached)

$3840000.0

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

48 Photos

1754 Pappy Gill Lane, Simcoe, ON , MLS #S13106296 , Image - 1

1754 Pappy Gill Lane Rural Severn, Severn, Simcoe, ON MLS® S13106296

Residential Freehold (Detached)

$3380000.0

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

STUNNING & IMMACULATE on Gloucester Pool! Discover the magic of this inland Muskoka gem, known for its calm waters, breathtaking natural shorelines, a

35 Photos

3476 Garden Of Eden Road, Simcoe, ON , MLS #S12660608 , Image - 1

3476 Garden Of Eden Road Rural Clearview, Clearview, Simcoe, ON MLS® S12660608

Residential Freehold (Rural Residential)

$3788000.0

Price drop by 5.3%

7 Beds
7 Baths
5000 + sq-ft

Set on an extraordinary 50-acre parcel just minutes from the heart of Creemore, this exceptional executive home offers refined living surrounded by a

41 Photos

1359 Old Barrie Road E, Simcoe, ON , MLS #S13021978 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13021978

Residential Freehold (Detached)

$2199900.0

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

Highest Quality From Top To Bottom Over 5000 SqFt Of Available Living Space, South Western Exposure Backyard For Beautiful Sunsets. One Of A Kind It F

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