609+ Detached Houses for Sale in Simcoe Under $5M

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238 Robins Point Road, Simcoe, ON , MLS #S12544504 , Image - 1

238 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S12544504

Residential Freehold (Detached)

$1495000.0

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

Top 5 Reasons You Will Love This Home: 1) Enjoy stunning waterfront living with over 50' of Georgian Bay frontage, offering expansive views and a layo

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282 Robins Point Road, Simcoe, ON , MLS #S12561534 , Image - 1

282 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S12561534

Residential Freehold (Detached)

$1149900.0

4 Beds
2 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) This waterfront home showcases breathtaking panoramic water views, creating a tranquil and scenic atmosphere

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2766 Ireton Street, Simcoe, ON , MLS #N12325788 , Image - 1

2766 Ireton Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N12325788

Residential Freehold (Detached)

$475000.0

3 Beds
1 Baths
700-1100 sq-ft

Incredible opportunity to build your dream home or cottage retreat on a premium lot just steps from one of Innisfil's most beautiful beaches. This exp

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57 Glenhuron Drive, Simcoe, ON , MLS #S12597102 , Image - 1

57 Glenhuron Drive Midhurst, Springwater, Simcoe, ON MLS® S12597102

Residential Freehold (Detached)

$4195000.0

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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2 WHITE PINES Trail, Simcoe, ON , MLS #S12596254 , Image - 1

2 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S12596254

Residential Freehold (Detached)

$134999.0

2 Beds
1 Baths
< 700 sq-ft

Enjoy your Seasonal Getaway at Wasaga Countrylife Resort! Now is the time to secure your seasonal cottage retreat! This immaculate 2009 Northlander Co

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118 Queen Street, Simcoe, ON , MLS #N12423433 , Image - 1

118 Queen Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12423433

Residential Freehold (Detached)

$899000.0

Price drop by 5.3%

3 +1 Beds
2 Baths
1100-1500 sq-ft

Nestled on a peaceful street in Bradford! This well-cared-for freshly painted bungalow is an excellent option for those looking to downsize or for fir

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726 Pennorth Drive, Simcoe, ON , MLS #S12555996 , Image - 1

726 Pennorth Drive Rural Tiny, Tiny, Simcoe, ON MLS® S12555996

Residential Freehold (Detached)

$1099900.0

5 Beds
3 Baths
2500-3000 sq-ft

Welcome To The Beach Life! This Well Maintained 5-Bedroom, 3-Bathroom, Home Or Cottage Sits Just A Short Walk From The Gorgeous Sand Beach And Crystal

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Lot 92A Reynolds Drive, Simcoe, ON , MLS #S12393579 , Image - 1

Lot 92A Reynolds Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12393579

Residential Freehold (Detached)

$559900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome To Lakepoint Village's Land Leased Community Located Just Outside Of Orillia With All The Amenities You Need! This Home Offers Elegant Main Fl

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Lot 89A Reynolds Drive, Simcoe, ON , MLS #S12393583 , Image - 1

Lot 89A Reynolds Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12393583

Residential Freehold (Detached)

$599900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome To Lakepoint Village's Land Leased Community Located Just Outside Of Orillia With All The Amenities You Need! This Home Offers Elegant Main Fl

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56 Birch Trail, Simcoe, ON , MLS #S12566242 , Image - 1

56 Birch Trail Wasaga Beach, Simcoe, ON MLS® S12566242

Residential Freehold (Detached)

$549777.0

1 Beds
2 Baths
< 700 sq-ft

Charming A-Frame Cottage Just a 9-Minute Walk from Allenwood Beach. Nestled at the end of a tranquil cul-de-sac, this delightful A-frame cottage is on

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7177 Beach Drive, Simcoe, ON , MLS #S12071905 , Image - 1

7177 Beach Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12071905

Residential Freehold (Detached)

$614900.0

Price drop by 90.5%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to Floral Park, Enjoy lake living without high costs of lakefront. One minute walk to government dock on lake couchiching where you can launch

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16 Roy Road, Simcoe, ON , MLS #N12464703 , Image - 1

16 Roy Road Tottenham, New Tecumseth, Simcoe, ON MLS® N12464703

Residential Freehold (Detached)

$1568000.0

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

Step into a masterpiece where luxury meets tranquility in Tottenham's most coveted enclave! This extraordinary home, the largest builder model, rests

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37 Loon Avenue, Simcoe, ON , MLS #S12544678 , Image - 1

37 Loon Avenue Painswick South, Barrie, Simcoe, ON MLS® S12544678

Residential Freehold (Detached)

$699900.0

4 Beds
3 Baths
1500-2000 sq-ft

Multi-Family, Flip, or Investment Opportunity in Central Barrie - Sellers Willing to Rent Back! Located minutes from Hwy 400, major shopping, schools,

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56 Georgian Manor Drive, Simcoe, ON , MLS #S12430539 , Image - 1

56 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S12430539

Residential Freehold (Detached)

$749000.0

Price drop by 9.2%

5 Beds
2 Baths
1500-2000 sq-ft

Welcome to 56 Georgian Manor Drive in beautiful Collingwood an incredible investment opportunity just minutes from Georgian Bay, downtown Collingwood

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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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2371 Lakeshore Road E, Simcoe, ON , MLS #S12527924 , Image - 1

2371 Lakeshore Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S12527924

Residential Freehold (Detached)

$1925000.0

2 +1 Beds
2 Baths
1500-2000 sq-ft

Welcome to this beautifully renovated bungalow, perfectly positioned on the inviting shores of Lake Simcoe. This home is an ideal retreat for those wh

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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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209 Barrie Street, Simcoe, ON , MLS #N12542736 , Image - 1

209 Barrie Street Thornton, Essa, Simcoe, ON MLS® N12542736

Residential Freehold (Detached)

$699999.0

4 Beds
2 Baths
1500-2000 sq-ft

Welcome to 209 Barrie St, a truly remarkable property in the heart of Thornton! Situated on an expansive 114' x 294' lot, offering over 3/4 of an acre

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2082 Lea Road, Simcoe, ON , MLS #N12553568 , Image - 1

2082 Lea Road Alcona, Innisfil, Simcoe, ON MLS® N12553568

Residential Freehold (Detached)

$899900.0

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

21000 Sqft Lot With Mixed Use Zoning. Second Access From Innisfil Beach Rd. Minutes To Beaches, Amenities, And Lake Simcoe. Enjoy Your Large Private B

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5 Culbert Road, Simcoe, ON , MLS #N12299513 , Image - 1

5 Culbert Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12299513

Residential Freehold (Detached)

$1350000.0

3 Beds
3 Baths
2000-2500 sq-ft

5 Culbert Rd in Bradford is a brand-new, never-lived-in 3-bedroom, 3-bathroom home offering modern elegance and comfort. The main floor boasts approxi

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84 Atlantis Drive W, Simcoe, ON , MLS #S12456892 , Image - 1

84 Atlantis Drive W Orillia, Simcoe, ON MLS® S12456892

Residential Freehold (Detached)

$789900.0

4 Beds
3 Baths
2000-2500 sq-ft

**NO CARPET IN HOUSE** New Flooring Installed in July 2025. Welcome To 84 Atlantis Dr. A Home That Truly Checks All The Right Boxes. This Elegant, Mod

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6222 Bluebird Street, Simcoe, ON , MLS #S12534978 , Image - 1

6222 Bluebird Street Rural Ramara, Ramara, Simcoe, ON MLS® S12534978

Residential Freehold (Detached)

$579999.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to your affordable lakefront escape on the peaceful shores of Lake St. John! This cozy 2-bedroom, 1-bathroom four-season home is the perfect e

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57 Coldwater Road, Simcoe, ON , MLS #S12522580 , Image - 1

57 Coldwater Road Coldwater, Severn, Simcoe, ON MLS® S12522580

Residential Freehold (Detached)

$650000.0

3 Beds
2 Baths
1100-1500 sq-ft

Located just a short walk from the charming village centre of Coldwater, this beautifully updated century home combines character with modern comfort.

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309 Manly Street, Simcoe, ON , MLS #S12509724 , Image - 1

309 Manly Street Midland, Simcoe, ON MLS® S12509724

Residential Freehold (Detached)

$424900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 309 Manly Street in Midland. Whether you are looking for an investment or just starting out this property has upside potential. Featuring

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3769 Sunbank Crescent, Simcoe, ON , MLS #S12505476 , Image - 1

3769 Sunbank Crescent West Shore, Severn, Simcoe, ON MLS® S12505476

Residential Freehold (Detached)

$849888.0

4 Beds
3 Baths
2500-3000 sq-ft

Welcome to 3769 Sunbank Crescent! Practically Brand New (2023) Never Lived in, Ugraded Detached 2 Story 2 Car Garage on a Premium Pie Shaped Lot, Boas

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216 Foster Drive, Simcoe, ON , MLS #S12503250 , Image - 1

216 Foster Drive Painswick North, Barrie, Simcoe, ON MLS® S12503250

Residential Freehold (Detached)

$749800.0

3 +2 Beds
2 Baths
700-1100 sq-ft

Detached, newly renovated sun-filled raised bungalow situated on a quiet street with a huge 60 ft x 300 ft lot, and ample driveway parking. Very brigh

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210 Minnesota Street, Simcoe, ON , MLS #S12176825 , Image - 1

210 Minnesota Street Collingwood, Simcoe, ON MLS® S12176825

Residential Freehold (Detached)

$1499000.0

Price drop by 6.3%

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

Welcome to 210 Minnesota Street a home on one of Collingwood's most loved streets. There's a reason homes here rarely change hands. The street has a

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2858 LAKESHORE Road E, Simcoe, ON , MLS #S12501150 , Image - 1

2858 LAKESHORE Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12501150

Residential Freehold (Detached)

$1269900.0

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

Spectacular 5yr old Linwood Georgian II home with a great lake view of Carthew Bay! Shallow beach area makes this a perfect spot for families with chi

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5 Bourgeois Beach Road, Simcoe, ON , MLS #S12468089 , Image - 1

5 Bourgeois Beach Road Victoria Harbour, Tay, Simcoe, ON MLS® S12468089

Residential Freehold (Detached)

$639000.0

3 +1 Beds
2 Baths
1100-1500 sq-ft

Welcome to 5 Bourgeois Beach Road. This beautifully updated bungalow offers the perfect blend of comfort, privacy, and location. With a total of 2,316

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264 Robins Point Road, Simcoe, ON , MLS #S12462766 , Image - 1

264 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S12462766

Residential Freehold (Detached)

$1515000.0

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

Experience the ultimate waterfront lifestyle on Georgian Bay with this exceptional 122' property featuring two unique cottages. The charming log cotta

Detached Houses for Sale in Simcoe Under $5M - P20

Rosehaven Simcoe Woods