Simcoe, ON Luxury Homes For Sale | SquareYards

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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

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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

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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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376 Brewery Lane, Simcoe, ON , MLS #S12432210 , Image - 1

376 Brewery Lane Orillia, Simcoe, ON MLS® S12432210

Residential Freehold (Detached)

$4799000.0

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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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

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7781 Poplar Side Road, Simcoe, ON , MLS #S12188211 , Image - 1

7781 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12188211

Residential Freehold (Detached)

$6499000.0

5 Beds
7 Baths
5000 + sq-ft

Welcome to one of the most spectacular properties you will find located on the Clearview/Collingwood border just 2hrs from Toronto and located minutes

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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

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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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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

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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

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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

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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

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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

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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

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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

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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

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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

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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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53 Niagara Street, Simcoe, ON , MLS #S12399959 , Image - 1

53 Niagara Street Collingwood, Simcoe, ON MLS® S12399959

Residential Freehold (Detached)

$2399000.0

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

NEW PRICE & STEPS TO SUNSET POINT, GEORGIAN BAY - this custom Vandermeer-designed 5-bedroom home offers over 3,700 sq. ft. of beautifully finished li

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45 Mary Street, Simcoe, ON , MLS #S12039966 , Image - 1

45 Mary Street Collingwood, Simcoe, ON MLS® S12039966

Residential Freehold (Detached)

$2400000.0

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

***BUILD IN PROGRESS*** Luxury Custom Home on Mary Street, Collingwood. Currently under construction by a quality local builder, this stunning custom

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60 Marni Lane, Simcoe, ON , MLS #S12282963 , Image - 1

60 Marni Lane Phelpston, Springwater, Simcoe, ON MLS® S12282963

Residential Freehold (Detached)

$2388000.0

Price drop by 7.3%

4 Beds
3 Baths
3000-3500 sq-ft

Quality builder, Tarion warranty included! Brand New. Sprawling 3200 sq ft Custom stone and brick bungalow on over an acre. From the large entrance wa

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31 Paradise Boulevard, Simcoe, ON , MLS #S12484661 , Image - 1

31 Paradise Boulevard Rural Ramara, Ramara, Simcoe, ON MLS® S12484661

Residential Freehold (Detached)

$2199000.0

3 Beds
3 Baths
3500-5000 sq-ft

Almost 4, 200 Sqft of living space detached home. Stunning and beautiful home backing on canal leading to Lake Simcoe. Chef's kitchen with side by sid

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