Simcoe, ON Luxury Homes For Sale | SquareYards

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1189 Woodland Drive, Simcoe, ON , MLS #S13607388 , Image - 1

1189 Woodland Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13607388

Residential Freehold (Detached)

$2999900.0

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

Some properties offer waterfront. Others offer a lifestyle that simply can't be replicated. From the curb appeal to the breathtaking lake views the mo

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955 Big Bay Point Road, Simcoe, ON , MLS #N13555904 , Image - 1

955 Big Bay Point Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13555904

Residential Freehold (Vacant Land)

$4500000.0

Strategically located within the highly desirable Big Bay Point corridor, this exceptional 50-acre landholding offers a rare opportunity to acquire a

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105-111 Edgehill Drive, Simcoe, ON , MLS #S13589824 , Image - 1

105-111 Edgehill Drive Edgehill Drive, Barrie, Simcoe, ON MLS® S13589824

Residential Freehold (Vacant Land)

$3900000.0

Exceptional residential infill development opportunity in Barrie. 1.88-acre site zoned RM2 (SP-575) with a new Site Plan being submitted for a 36-unit

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6 Pinehurst Lane, Simcoe, ON , MLS #S13523312 , Image - 1

6 Pinehurst Lane Anten Mills, Springwater, Simcoe, ON MLS® S13523312

Residential Freehold (Detached)

$2600000.0

Price drop by 1.9%

6 +3 Beds
6 Baths
5000 + sq-ft

Experience the ultimate retreat in this stunning custom-built estate on a private 1.62-acre lot minutes from Barrie. Designed for discerning buyers se

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11 Byers Street, Simcoe, ON , MLS #S13174312 , Image - 1

11 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S13174312

Residential Freehold (Detached)

$2499900.0

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

Exceptional executive bungalow on a premium estate lot in prestigious Cameron Estates, offering incredible curb appeal and a resort-inspired rear yard

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3316 Point Bush Court, Simcoe, ON , MLS #S13082362 , Image - 1

3316 Point Bush Court Port Severn, Severn, Simcoe, ON MLS® S13082362

Residential Freehold (Detached)

$2699000.0

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

Where waterfront living meets everyday comfort, this custom-built four-season retreat sits on a picturesque point of land on Little Lake, offering sou

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6920 Poplar Side Road, Simcoe, ON , MLS #S13602452 , Image - 1

6920 Poplar Side Road Collingwood, Simcoe, ON MLS® S13602452

Residential Freehold (Detached)

$2399900.0

4 Beds
4 Baths
3000-3500 sq-ft

Welcome to 6920 Poplar Side Road, a stunning custom-built estate on nearly 1.8 acres in Collingwood. Offering 3430 sqft above grade plus an unfinished

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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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1031 Wisker Avenue, Simcoe, ON , MLS #N13595944 , Image - 1

1031 Wisker Avenue Lefroy, Innisfil, Simcoe, ON MLS® N13595944

Residential Freehold (Detached)

$2888000.0

5 Beds
3 Baths
2500-3000 sq-ft

Unbelievable opportunity to own a stunning, fully renovated (2023) five-bedroom waterfront home on a massive 138' x 141' double lot in one of the most

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8058 20th Side Road, Simcoe, ON , MLS #N13580044 , Image - 1

8058 20th Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13580044

Residential Freehold (Detached)

$2500000.0

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

Welcome to your ultimate rural investment opportunity! Nestled on 21 pristine gated acres in highly desirable equestrian country, the versatile estate

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4 Raintree Court, Simcoe, ON , MLS #S13594758 , Image - 1

4 Raintree Court Rural Clearview, Clearview, Simcoe, ON MLS® S13594758

Residential Freehold (Detached)

$4995000.0

4 +1 Beds
7 Baths
5000 + sq-ft

Welcome to the extraordinary, four season resort experience offered by 4 Raintree Court, nestled in the heart of Ontario's ski country. This luxurious

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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)

$3499000.0

Price drop by 12.5%

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

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2710 Nottawasaga 10 Concession N, Simcoe, ON , MLS #S13593190 , Image - 1

2710 Nottawasaga 10 Concession N Rural Clearview, Clearview, Simcoe, ON MLS® S13593190

Residential Freehold (Detached)

$3975000.0

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

Introducing Winterbrook, a luxurious custom estate home masterfully crafted by Dalton Beachli. Nestled on just under two acres of beautifully landscap

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15 Palm Beach Road, Simcoe, ON , MLS #S13502062 , Image - 1

15 Palm Beach Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13502062

Residential Freehold (Detached)

$2299999.0

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

Set along the pristine shores of Lake Simcoe, this exceptional waterfront estate offers a rare blend of privacy, prestige, and resort-style living, pe

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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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6863 Fifth Line, Simcoe, ON , MLS #N13588520 , Image - 1

6863 Fifth Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13588520

Residential Freehold (Farm)

$15800000.0

< 700 sq-ft

Exceptional Power of Sale opportunity to acquire a (6863a 10.16 and 6863 89.46) combined 99.62 acres of contiguous, largely vacant land with frontage

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846 Sixth Street, Simcoe, ON , MLS #S13563542 , Image - 1

846 Sixth Street Rural Clearview, Clearview, Simcoe, ON MLS® S13563542

Residential Freehold (Detached)

$2499000.0

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

Luxury Custom Home with Income Suite - Over 6,000 Sq Ft of Finished Living SpaceDiscover this stunning, one-of-a-kind luxury custom home, perfectly si

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6863a Fifth Line, Simcoe, ON , MLS #N13588156 , Image - 1

6863a Fifth Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13588156

Residential Freehold (Farm)

$2500000.0

< 700 sq-ft

Exceptional Power of Sale / Receivership opportunity to acquire a combined - (6863a 10.16 and 6863 89.46) and Adjacent 99.62 acres of contiguous, larg

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18 Carrol Lane Waubaushene, Tay, Simcoe, ON MLS® S13492722

Residential Freehold (Vacant Land)

$11500000.0

This 26-acre property in the Town of Tay, located just 2 minutes from Highway 400 and offering convenient access (roughly an hour from Vaughan, 35 min

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168 Pine Hill Road, Simcoe, ON , MLS #N13557218 , Image - 1

168 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13557218

Residential Freehold (Detached)

$2348000.0

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to 168 Pine Hill Road, an extraordinary executive estate nestled on a breathtaking 1.38 acre private lot in one of Bradford's most prestigious

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2166 10th Side Road, Simcoe, ON , MLS #N13527220 , Image - 1

2166 10th Side Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13527220

Residential Freehold (Detached)

$3368800.0

6 +1 Beds
9 Baths
5000 + sq-ft

Generational Living at it's finest in Bradford's exclusive area. 2min to HWY 400. Feel the magnificence of this one of a kind property the second you

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57 Alpine Drive, Simcoe, ON , MLS #S13576842 , Image - 1

57 Alpine Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13576842

Residential Freehold (Detached)

$2385000.0

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

Welcome to this stunning, new estate bungalow located in a quiet community just 5 minutes from a 36 slope ski resort and snowmobile trails. With quick

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3692 Ferretti Court, Simcoe, ON , MLS #N13521406 , Image - 1

3692 Ferretti Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13521406

Residential Freehold (Att/Row/Townhouse)

$2500000.0

Price drop by 13.8%

4 Beds
5 Baths
2500-3000 sq-ft

Step into this beautifully appointed corner townhome at Friday Harbour, fully furnished and enhanced with over $300,000 in custom upgrades. This water

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4229 Wilson Point Road N, Simcoe, ON , MLS #S13466754 , Image - 1

4229 Wilson Point Road N Rural Severn, Severn, Simcoe, ON MLS® S13466754

Residential Freehold (Detached)

$2499000.0

4 Beds
6 Baths
3500-5000 sq-ft

Commanding one of the finest lots on Lake Couchiching, this exceptional waterfront estate is positioned at the end of a quiet dead-end street, offerin

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9 Barrie Terrace, Simcoe, ON , MLS #S13537858 , Image - 1

9 Barrie Terrace Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13537858

Residential Freehold (Detached)

$3699900.0

1 +3 Beds
3 Baths
3000-3500 sq-ft

Welcome to one of Barrie's most exceptional waterfront offerings. Nestled along the shores of Kempenfelt Bay on one of the city's most coveted streets

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1036 River Road E, Simcoe, ON , MLS #S13171888 , Image - 1

1036 River Road E Wasaga Beach, Simcoe, ON MLS® S13171888

Residential Freehold (Detached)

$2500000.0

4 Beds
3 Baths
2500-3000 sq-ft

A HOME FOR ALL SEASONS! With immediate access to the sandy shores of Allenwood Beach, this private, custom-built, four bedroom, three bathroom bungalo

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8464 6th Line, Simcoe, ON , MLS #N13561726 , Image - 1

8464 6th Line Rural Essa, Essa, Simcoe, ON MLS® N13561726

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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5 17th Street N, Simcoe, ON , MLS #S13561556 , Image - 1

5 17th Street N Wasaga Beach, Simcoe, ON MLS® S13561556

Residential Freehold (Detached)

$2800000.0

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

A MASTERPIECE OF COASTAL PRESTIGE DIRECTLY ON GEORGIAN BAY! Pull through the gated entry and Georgian Bay unfolds before you, creating a waterfront es

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7665 36/37 NOTTAWASAGA Side Road W, Simcoe, ON , MLS #S13496572 , Image - 1

7665 36/37 NOTTAWASAGA Side Road W Nottawa, Clearview, Simcoe, ON MLS® S13496572

Residential Freehold (Detached)

$3499000.0

5 Beds
3 Baths
5000 + sq-ft

Prepare to be captivated. Set on 18 private acres overlooking the breathtaking Pretty River, this extraordinary custom-built log home is a masterpiece

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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)

$5250000.0

Price drop by 4.4%

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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