890+ Houses for Sale in Simcoe Under $5 Million

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16 SUNWARD Drive, Simcoe, ON , MLS #S12442588 , Image - 1

16 SUNWARD Drive Wasaga Beach, Simcoe, ON MLS® S12442588

Residential Freehold (Vacant Land)

$599000.0

Perfect Building lot for TWO homes. This rare opportunity doesn't come by often where you find a lot that has access to 2 thru roads. Measuring 100 x

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7 Purple Hill Lane, Simcoe, ON , MLS #S12405373 , Image - 1

7 Purple Hill Lane Creemore, Clearview, Simcoe, ON MLS® S12405373

Residential Freehold (Detached)

$2190000.0

5 +1 Beds
4 Baths
2500-3000 sq-ft

Discover your own private retreat in this 4,297 sqft resort-style home set on 1.84 acres of beautifully landscaped grounds. With a 3-car garage, 12 pe

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31 Sweet Cicely Street, Simcoe, ON , MLS #S12454638 , Image - 1

31 Sweet Cicely Street Midhurst, Springwater, Simcoe, ON MLS® S12454638

Residential Freehold (Detached)

$919990.0

Price drop by 5.2%

4 Beds
4 Baths
2500-3000 sq-ft

Situated in the prestigious Midhurst Valley Community this 2,630 sq ft. home, crafted by the award-winning Brookfield Residential, is a sanctuary of n

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60 Carley Crescent, Simcoe, ON , MLS #S12668560 , Image - 1

60 Carley Crescent Painswick South, Barrie, Simcoe, ON MLS® S12668560

Residential Freehold (Detached)

$889000.0

4 Beds
3 Baths
2500-3000 sq-ft

Welcome to this beautifully cared-for all-brick family home, nestled on a quiet crescent in one of Barrie's most sought-after neighborhoods. From the

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221 JANE Street, Simcoe, ON , MLS #S12451972 , Image - 1

221 JANE Street Stayner, Clearview, Simcoe, ON MLS® S12451972

Residential Freehold (Detached)

$999900.0

4 +0 Beds
4 Baths
3000-3500 sq-ft

DETACHED SHOP + SECOND DRIVEWAY. In Law capability. Welcome to this charming piece of paradise in the heart of Stayner. Nestled on a PRIVATE 93' x 158

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16 Wales Avenue N, Simcoe, ON , MLS #N12668208 , Image - 1

16 Wales Avenue N Everett, Adjala-Tosorontio, Simcoe, ON MLS® N12668208

Residential Freehold (Detached)

$899000.0

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

Welcome to 16 Wales Ave N - Situated on an impressive 78 x 167-foot lot, this beautifully updated 3+2 bedroom bungalow offers an unbeatable combinatio

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10 INVERMARA Court, Simcoe, ON , MLS #S12503218 , Image - 1

Unit-28, 10 INVERMARA Court Orillia, Simcoe, ON MLS® S12503218

Residential Freehold (Detached)

$949900.0

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

Nestled in a private, gated community on the shores of Lake Simcoe in the heart of Orillia, this beautifully updated executive home offers over 2,250

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24 Brennan Avenue, Simcoe, ON , MLS #S12665924 , Image - 1

24 Brennan Avenue South Shore, Barrie, Simcoe, ON MLS® S12665924

Residential Freehold (Detached)

$625000.0

3 Beds
1 Baths
1100-1500 sq-ft

Builders , 1st time home buyers, developers , so many opportunities for this 50' property that fronts 2 roads in Barrie's highly desirable Minet's poi

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3718 Mangusta Court, Simcoe, ON , MLS #N12665456 , Image - 1

3718 Mangusta Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N12665456

Residential Freehold (Att/Row/Townhouse)

$1599999.0

3 Beds
5 Baths
2000-2500 sq-ft

Discover the epitome of luxurious 4-seasons waterfront living at 3718 Mangusta, a marvel that blends sophistication &comfort, nestled on a private & g

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9 Harbour Street E, Simcoe, ON , MLS #S12099425 , Image - 1

Unit-3109-3111, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12099425

Residential Condo & Other (Other)

$78000.0

2 Beds
2 Baths
1200-1399 sq-ft

This 3 week G6 fractional ownership for weeks 31-33-46, with a spectacular view of Georgian Bay and historic Collingwood grain terminals could be your

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1 Fortuna Circle, Simcoe, ON , MLS #N12658538 , Image - 1

Unit-20, 1 Fortuna Circle Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12658538

Residential Condo & Other (Detached Condo)

$869000.0

2 +1 Beds
3 Baths
1400-1599 sq-ft

STUNNING BUNGALOFT IN THE GOLFING COMMUNITY OF BRIAR HILL! Extensive renovations dressed to impress from top to bottom! Entertain in style with the gr

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65 Crimson Ridge Road, Simcoe, ON , MLS #S12664360 , Image - 1

65 Crimson Ridge Road Bayshore, Barrie, Simcoe, ON MLS® S12664360

Residential Freehold (Detached)

$1099000.0

3 Beds
3 Baths
2000-2500 sq-ft

Stunning Detached Home Located in a sought-after neighborhood. Features a double garage with inside entry, hardwood and ceramic flooring throughout, a

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178 Barrie Street, Simcoe, ON , MLS #N12663972 , Image - 1

178 Barrie Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12663972

Residential Freehold (Detached)

$949999.0

4 Beds
2 Baths
1500-2000 sq-ft

Rare Opportunity in the Heart of Bradford! This tastefully renovated and modernized home offers 2 fully separate main floor units, perfect for investo

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93 Bayshore Drive, Simcoe, ON , MLS #S12087968 , Image - 1

93 Bayshore Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12087968

Residential Freehold (Detached)

$948000.0

Price drop by 11.8%

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

Welcome home to this wonderful 4-bedroom, 3-bath home in the prestigious Bayshore Village waterfront community. Backing onto a tranquil pond, this pro

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1417 Gilford Road, Simcoe, ON , MLS #N12662114 , Image - 1

1417 Gilford Road Gilford, Innisfil, Simcoe, ON MLS® N12662114

Residential Freehold (Detached)

$1399900.0

5 Beds
3 Baths
3000-3500 sq-ft

Here is your chance to own a stunning bungaloft-style home located in the tranquil Gilford, Ontario. This 5-bedroom, 3-bathroom residence offers over

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155 Webb Street, Simcoe, ON , MLS #N12661896 , Image - 1

155 Webb Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12661896

Residential Freehold (Detached)

$949000.0

3 Beds
3 Baths
1500-2000 sq-ft

Discover this stunning 2-storey detached home, built in 2013, offering the perfect blend of modern style, comfort, and convenience. With 3 generous be

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439 Sundial Drive, Simcoe, ON , MLS #S12491190 , Image - 1

439 Sundial Drive Orillia, Simcoe, ON MLS® S12491190

Residential Freehold (Detached)

$525000.0

3 Beds
1 Baths
700-1100 sq-ft

Situated on a generous 0.49-acre lot (approximately 60' x 330'), this raised bungalow offers a perfect blend of space and location. The home features

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23 Timcourt Drive, Simcoe, ON , MLS #S12661182 , Image - 1

23 Timcourt Drive Rural Tiny, Tiny, Simcoe, ON MLS® S12661182

Residential Freehold (Detached)

$1299900.0

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

Escape the city and embrace lakeside living! Located 15 minutes from Penetanguishene and under 2 hours from the GTA, this exceptional four-season lake

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4 Kimberly Lane

Unit-518, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® S12533272

Residential Condo & Other (Condo Apartment)

$749000.0

Price drop by 3.2%

2 Beds
2 Baths
1000-1199 sq-ft

Penthouse living at the brand new Royal Windsor! If you've been waiting for the best suite in the building, here it is. Suite 518 is a bright, open co

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17 Spooner Crescent, Simcoe, ON , MLS #S12660244 , Image - 1

Unit-205, 17 Spooner Crescent Collingwood, Simcoe, ON MLS® S12660244

Residential Condo & Other (Condo Apartment)

$445000.0

2 Beds
2 Baths
800-899 sq-ft

Are you looking for a simple, stress-free place to call home or escape on weekends? This bright and modern condo at The View at Blue Fairway could be

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1230 GRANDVIEW LODGE Road, Simcoe, ON , MLS #S12658886 , Image - 1

Unit-Beach Chalet #3, 1230 GRANDVIEW LODGE Road Rural Severn, Severn, Simcoe, ON MLS® S12658886

Residential Freehold (Att/Row/Townhouse)

$474900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 2026, wow that year went by quickly! Spring and summer are just around the corner so why not get you the summer vacation home of your dream

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22 Bourgeois Beach Road, Simcoe, ON , MLS #S12654316 , Image - 1

22 Bourgeois Beach Road Victoria Harbour, Tay, Simcoe, ON MLS® S12654316

Residential Freehold (Detached)

$917777.0

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

This one-owner, custom-built design and steps to Georgian Bay and the Trans Canada Trail offer a picturesque setting that's hard to resist. From the e

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8 Kelley Crescent, Simcoe, ON , MLS #S12658412 , Image - 1

8 Kelley Crescent Wasaga Beach, Simcoe, ON MLS® S12658412

Residential Freehold (Vacant Land)

$499900.0

5000 + sq-ft

A Rare Opportunity to build your dream home in the highly sought-after Wasaga Sands Golf Club community. This fully treed building lot backs onto gree

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58 Penetang Street, Simcoe, ON , MLS #S12657626 , Image - 1

Unit-1-4, 58 Penetang Street Codrington, Barrie, Simcoe, ON MLS® S12657626

Residential Freehold (Fourplex)

$794900.0

7 +0 Beds
4 Baths
2500-3000 sq-ft

INVESTORS!!! Looking to add to your real estate portfolio? Looking to enter into the real estate market and start your portfolio? Take a look today! G

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4 East Street, Simcoe, ON , MLS #S12657488 , Image - 1

4 East Street Wellington, Barrie, Simcoe, ON MLS® S12657488

Residential Freehold (Detached)

$549900.0

4 Beds
2 Baths
1500-2000 sq-ft

Property is being sold As is, Where is. Unique century home on 55 X 115 Lot close to downtown Barrie. The front portion of the home is the original

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1244 Mary-Lou Street, Simcoe, ON , MLS #N12462420 , Image - 1

1244 Mary-Lou Street Alcona, Innisfil, Simcoe, ON MLS® N12462420

Residential Freehold (Detached)

$785000.0

3 Beds
3 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Meticulously maintained and move-in ready, this spacious three bedroom, three bathroom home is ideally suite

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26 Robert Street E, Simcoe, ON , MLS #S12657176 , Image - 1

26 Robert Street E Penetanguishene, Simcoe, ON MLS® S12657176

Residential Freehold (Detached)

$749000.0

3 Beds
2 Baths
3000-3500 sq-ft

Perched on a hilltop in the heart of Penetanguishene, 26 Robert Street East is an exquisitely restored Edwardian century home offering timeless elegan

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4 KIMBERLY Lane, Simcoe, ON , MLS #S10438907 , Image - 1

Unit-207, 4 KIMBERLY Lane Collingwood, Simcoe, ON MLS® S10438907

Residential Condo & Other (Condo Apartment)

$749000.0

Price drop by 13.9%

2 +0 Beds
2 Baths
1200-1399 sq-ft

Welcome to Royal Windsor Condominiums in Beautiful Collingwood - This Brand new DYNASTY suite (1,305 Sq ft) has a two bedroom, two bathroom floor plan

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4 KIMBERLY Lane, Simcoe, ON , MLS #S10436897 , Image - 1

Unit-109, 4 KIMBERLY Lane Collingwood, Simcoe, ON MLS® S10436897

Residential Condo & Other (Condo Apartment)

$879000.0

Price drop by 10.8%

2 +0 Beds
2 Baths
1400-1599 sq-ft

Welcome to Royal Windsor Condominiums in Beautiful Collingwood - This Brand new KNIGHT suite (1,500 Sq ft) has a two bedroom, two bathroom. 2 (tandem)

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1369 Ryerson Boulevard, Simcoe, ON , MLS #S12655608 , Image - 1

1369 Ryerson Boulevard Rural Severn, Severn, Simcoe, ON MLS® S12655608

Residential Freehold (Detached)

$1249000.0

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

Welcome to tranquility surrounded by trees and nature. This newly renovated/un-lived in (upper) country home sits on 10 acres of land with plenty of l

Houses for Sale in Simcoe Under $5 Million - P20

Rosehaven Simcoe Woods