975+ Houses for Sale in Simcoe Under $5 Million

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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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2728 25th Side Road, Simcoe, ON , MLS #N12108250 , Image - 1

2728 25th Side Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N12108250

Residential Freehold (Vacant Land)

$399900.0

Price drop by 10.9%

Attention builders and investors! Great Opportunity to build your dream home on this rare 1 Acre sized property. Just steps away from Lake Simcoe and

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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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41 Paradise Boulevard, Simcoe, ON , MLS #S12429470 , Image - 1

41 Paradise Boulevard Brechin, Ramara, Simcoe, ON MLS® S12429470

Residential Freehold (Vacant Land)

$999000.0

Premium lot on the main channel in Beautiful Lagoon City. This lot is ready to build, with permits, foundation and piles in place for a 6000 + sq ft s

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90 Dean Avenue, Simcoe, ON , MLS #S8364164 , Image - 1

Unit-417, 90 Dean Avenue Painswick South, Barrie, Simcoe, ON MLS® S8364164

Residential Condo & Other (Leasehold Condo)

$399900.0

Price drop by 10.8%

1 Beds
1 Baths
800-899 sq-ft

The Terraces of Heritage Square is a Adult over 60+ building. These buildings have lots to offer, Party rooms, library, computer room and a second lev

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29 Nelson Street, Simcoe, ON , MLS #S12217295 , Image - 1

29 Nelson Street Creemore, Clearview, Simcoe, ON MLS® S12217295

Residential Freehold (Vacant Land)

$324900.0

Visit REALTOR website for additional information. Dreaming of a quieter lifestyle in a charming small town? This recently severed 50 x 165 lot in Cree

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552 10 Line S, Simcoe, ON , MLS #S12304965 , Image - 1

552 10 Line S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12304965

Residential Freehold (Vacant Land)

$999000.0

1100-1500 sq-ft

96 Acres of Opportunity, First Time Available in Over 65 Years! Discover the perfect blend of space, location, and potential with this expansive 96-ac

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Lot 354 Desroches Trail N/A NW, Simcoe, ON , MLS #S12215407 , Image - 1

Lot 354 Desroches Trail N/A NW Rural Tiny, Tiny, Simcoe, ON MLS® S12215407

Residential Freehold (Vacant Land)

$229000.0

TINY!!! BEST DESTINATION TO LIVE YOUR DREAMS. BUILD YOUR DREAM HOME AT THE BEACH! This one of a kind 100x150 corner lot is within 1 minutes to Lafonta

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7183 Hwy 93 Highway, Simcoe, ON , MLS #S12576032 , Image - 1

7183 Hwy 93 Highway Rural Tay, Tay, Simcoe, ON MLS® S12576032

Residential Freehold (Vacant Land)

$175000.0

Opportunity knocks at 7183 Highway 93 in the growing community of Wyebridge. This prime piece of land is an excellent option for builders, investors,

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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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2616 Grand Tamarack Crescent, Simcoe, ON , MLS #S12556258 , Image - 1

2616 Grand Tamarack Crescent West Shore, Severn, Simcoe, ON MLS® S12556258

Residential Freehold (Att/Row/Townhouse)

$529000.0

3 Beds
4 Baths
1500-2000 sq-ft

Welcome to this bright and beautifully maintained three-storey freehold townhouse offering approximately1,880 sq ft of finished living space only ten

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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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2149 Conc 5 N N/A, Simcoe, ON , MLS #S12554280 , Image - 1

2149 Conc 5 N N/A Rural Clearview, Clearview, Simcoe, ON MLS® S12554280

Residential Freehold (Vacant Land)

$149000.0

< 700 sq-ft

Over half acre lot that would qualify for a building permit if combined with a neighbouring lot but presently just a nicely treed lot for weekend enjo

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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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1430 COUNTY RD 50 N/A S, Simcoe, ON , MLS #N9362823 , Image - 1

1430 COUNTY RD 50 N/A S Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N9362823

Residential Freehold (Vacant Land)

$900000.0

This picturesque 10-acre parcel of rolling land in Adjala-Tosorontio Township offers stunning, clear views in every direction, making it the ideal loc

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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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241 Sea Ray Avenue, Simcoe, ON , MLS #N12537114 , Image - 1

Unit-A101, 241 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12537114

Residential Condo & Other (Condo Apartment)

$538888.0

2 Beds
2 Baths
800-899 sq-ft

This is your chance to own a slice of luxury vacation living, just one hour from the GTA. Whether you're looking for a full-time home, weekend escape,

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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.

Houses for Sale in Simcoe Under $5 Million - P31

Rosehaven Simcoe Woods