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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: November 14, 2025

40 Photos

17 Swan Lane, Simcoe, ON , MLS #S12544864 , Image - 1

17 Swan Lane Port McNicoll, Tay, Simcoe, ON MLS® S12544864

Residential Freehold (Detached)

$2499000.0

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

Luxury Waterfront Estate with Private Guest House & Income Potential. Welcome to 17 Swan Lane, a rare opportunity to own a stunning waterfront residen

46 Photos

201 Cedar Island Road, Simcoe, ON , MLS #S12151443 , Image - 1

201 Cedar Island Road Orillia, Simcoe, ON MLS® S12151443

Residential Freehold (Detached)

$2599900.0

3 Beds
4 Baths
2000-2500 sq-ft

Tucked along a quiet bay on Lake Couchiching, this stunning waterfront cottage or year-round home offers the peaceful lifestyle you've been dreaming o

40 Photos

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

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10 BROLLEY Crescent, Simcoe, ON , MLS #N12544620 , Image - 1

10 BROLLEY Crescent Rural Essa, Essa, Simcoe, ON MLS® N12544620

Residential Freehold (Detached)

$2149900.0

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

Presenting 10 Brolley Crescent, an exceptional custom-built home in one of the most prestigious neighbourhoods in Essa Township. Sitting on a professi

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

50 Photos

95 Spruce Street, Simcoe, ON , MLS #S12358712 , Image - 1

95 Spruce Street Rural Tiny, Tiny, Simcoe, ON MLS® S12358712

Residential Freehold (Detached)

$3500000.0

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

Introducing this luxurious, resort-like smart technology home or cottage near the pristine shores of Georgian Bay. Spanning over 2800 sq. ft. on the m

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8464 6th Line, Simcoe, ON , MLS #N12295252 , Image - 1

8464 6th Line Rural Essa, Essa, Simcoe, ON MLS® N12295252

Residential Freehold (Detached)

$2500000.0

4 Beds
3 Baths
3500-5000 sq-ft

LUXURY, SPACE, AND OPPORTUNITY - 4,544 SQ FT ESTATE ON 10 ACRES WITH OUTBUILDINGS BUILT FOR BUSINESS! Live the rural estate dream with this 4,544 sq f

25 Photos

8747 10th Line, Simcoe, ON , MLS #N12438171 , Image - 1

8747 10th Line Rural Essa, Essa, Simcoe, ON MLS® N12438171

Residential Freehold (Detached)

$2295000.0

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

OVER 3,000 SQ FT BUNGALOW FEATURING IN-LAW POTENTIAL NESTLED ON 83.47 ACRES WITH WORKABLE LAND & MINUTES TO BARRIE! Nestled on an expansive 83.47 acre

32 Photos

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

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

This waterfront property in Oro-Medonte sits on a 0.57-acre lot with 81 feet of clear shoreline and a private, shallow cove that gradually deepens to

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

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854 Sixth Street, Simcoe, ON , MLS #S12542318 , Image - 1

854 Sixth Street Rural Clearview, Clearview, Simcoe, ON MLS® S12542318

Residential Freehold (Detached)

$2699000.0

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

* Ask about potential severance of 2 Acre parcel* Nestled on 19 breathtaking acres just minutes from the vibrant heart of Collingwood and the world-cl

50 Photos

8429 Poplar Side Road, Simcoe, ON , MLS #S12537646 , Image - 1

8429 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12537646

Residential Freehold (Detached)

$3299000.0

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

Welcome to The Great Totem House, a stunning reclaimed timber frame chalet set on a private 1.3-acre forested lot, just minutes from Osler Bluff Ski C

40 Photos

2705 14th Line, Simcoe, ON , MLS #N12495028 , Image - 1

2705 14th Line Gilford, Innisfil, Simcoe, ON MLS® N12495028

Residential Freehold (Detached)

$2430000.0

Price drop by 4.1%

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

Welcome to this exceptional 3+2 bedroom, 5 bathroom custom-built estate home set on a private 3.25-acre treed property, offering luxury country living

32 Photos

1398 Old Second Road N, Simcoe, ON , MLS #S12490196 , Image - 1

1398 Old Second Road N Phelpston, Springwater, Simcoe, ON MLS® S12490196

Residential Freehold (Detached)

$2699900.0

3 +0 Beds
2 Baths
2000-2500 sq-ft

Welcome to your private country retreat nestled on 78 sprawling acres in the heart of Springwater, this extraordinary property offers the perfect blen

33 Photos

44-46 Gray Lane, Simcoe, ON , MLS #S12518308 , Image - 1

44-46 Gray Lane Innis-Shore, Barrie, Simcoe, ON MLS® S12518308

Residential Freehold (Detached)

$6499900.0

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

LUXURY WATERFRONT ESTATE HOME ON LAKE SIMCOE! ONE OF BARRIE'S MOST BEAUTIFUL HOMES! CUSTOM BUILT RETREAT WITH AN INGROUND POOL, FULL SIZE TENNIS/SPO

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1918 Concession Rd 2 N/A, Simcoe, ON , MLS #N12412220 , Image - 1

1918 Concession Rd 2 N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12412220

Residential Freehold (Detached)

$2750000.0

6 Beds
3 Baths
2500-3000 sq-ft

Exceptional 100-acre farm in South Adjala, surrounded by estate properties and just minutes from Caledon. Features gently rolling farmland with approx

50 Photos

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

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

Residential Freehold (Detached)

$3090000.0

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

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

45 Photos

9 Monica Road, Simcoe, ON , MLS #S12532648 , Image - 1

9 Monica Road Rural Tiny, Tiny, Simcoe, ON MLS® S12532648

Residential Freehold (Detached)

$3999000.0

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

A rare opportunity to own over 300 feet of private Georgian Bay waterfront in one of Tinys most coveted enclaves. Set on 2+ acres with unobstructed vi

40 Photos

6 Pinehurst Lane, Simcoe, ON , MLS #S12415757 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S12415757

Residential Freehold (Detached)

$2745000.0

6 +3 Beds
6 Baths
5000 + sq-ft

STUNNING Executive Custom Home in Springwater w/Breathtaking Views! Welcome to 7,864 Sq. Ft. of Living Space! Be Prepared to be Amazed. As you enter,

41 Photos

17 Bellflower Crescent, Simcoe, ON , MLS #N12526910 , Image - 1

17 Bellflower Crescent Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N12526910

Residential Freehold (Detached)

$2099000.0

5 Beds
5 Baths
5000 + sq-ft

This brand-new, **NEVER LIVED IN** luxury detached house sits on a premium **70-foot lot** and features a **Triple-car garage*** with a **10-car parki

13 Photos

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

5 Photos

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

50 Photos

2230 Spring Street, Simcoe, ON , MLS #N12473997 , Image - 1

2230 Spring Street Alcona, Innisfil, Simcoe, ON MLS® N12473997

Residential Freehold (Detached)

$3736000.0

4 Beds
2 Baths
2000-2500 sq-ft

A beautifully renovated 4-bedroom HOME on 1.96 ACRES, complete with a serene pond. In addition you could add an additional fully serviced 2.56-acre lo

6 Photos

476 Penetanguishene Road, Simcoe, ON , MLS #S4439718 , Image - 1

476 Penetanguishene Road Rural Springwater, Springwater, Simcoe, ON MLS® S4439718

Residential Freehold (Farm)

$5000000.0

< 700 sq-ft

Excellent Prospecting Land Located 1Km From Barrie. Next To Mini Storage, Golf Course, And City Wells.Currently Being Rented Out As Farm Land For Cash

5 Photos

Pt Lt20 Concession 7 Drive, Simcoe, ON , MLS #S4701501 , Image - 1

Pt Lt20 Concession 7 Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S4701501

Residential Freehold (Farm)

$10000000.0

< 700 sq-ft

Attention Investors And Farmers! This Property Abuts The Lake Simcoe Regional Airport (Airport Allows Small Jets). 137 Acres Of Farm/Vacant Land. Curr

50 Photos

28 Alana Drive, Simcoe, ON , MLS #S12510962 , Image - 1

28 Alana Drive Centre Vespra, Springwater, Simcoe, ON MLS® S12510962

Residential Freehold (Detached)

$2299900.0

4 Beds
3 Baths
3500-5000 sq-ft

Discover luxurious living in this beautifully redesigned Stonegate Estates home, offering 3,600+ sq. ft. of elegant, turn-key space. Professionally cu

49 Photos

237 West Shore Drive, Simcoe, ON , MLS #S12508920 , Image - 1

237 West Shore Drive Rural Tiny, Tiny, Simcoe, ON MLS® S12508920

Residential Freehold (Detached)

$2688000.0

5 Beds
3 Baths
1100-1500 sq-ft

Indulge In Luxury At 237 West Shore Dr., Tiny Exclusive Location In Thunder Beach. Approximately 2500 sq.ft of total living space. This 5-bed, 3-bath

40 Photos

2993 Innisfil Beach Road, Simcoe, ON , MLS #N12500820 , Image - 1

2993 Innisfil Beach Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N12500820

Residential Freehold (Detached)

$4999999.0

2 +2 Beds
4 Baths
1100-1500 sq-ft

Welcome to 2993 Innisfil Beach Road, a private luxury estate nestled on 19.17 acres of Muskoka-like landscape in the heart of Innisfil. Designed for t

50 Photos

57 Glenhuron Drive, Simcoe, ON , MLS #S12181041 , Image - 1

57 Glenhuron Drive Midhurst, Springwater, Simcoe, ON MLS® S12181041

Residential Freehold (Detached)

$4500000.0

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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206 Foster Drive Painswick North, Barrie, Simcoe, ON MLS® S12506966

Residential Freehold (Vacant Land)

$3000000.0

Presenting 206 Foster Dr in the heart of Barrie! 1.25 acre flat property designated as a Strategic Growth Area in the Town's Official Plan. Great oppo

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