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Houses for Sale in Orillia ON Under $500K

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Are you looking for houses under $500k for sale in Orillia ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Orillia. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Orillia. Whether you’re looking to buy houses under under $500k in Orillia ON for residential living or as investment opportunities, our listings allow you to filter by amenities, property age, number of bedrooms and much more. Explore a diverse range of Orillia houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: December 05, 2025

32 Photos

325 West N Street, Simcoe, ON , MLS #S12388344 , Image - 1

Unit-15, 325 West N Street Orillia, Simcoe, ON MLS® S12388344

Residential Condo & Other (Condo Townhouse)

$459900.0

3 +1 Beds
2 Baths
1000-1199 sq-ft

This bright and spacious townhome is the perfect opportunity for those seeking comfortable, affordable living without compromise. Offering four bedroo

28 Photos

147 Dufferin Street, Simcoe, ON , MLS #S12172960 , Image - 1

147 Dufferin Street Orillia, Simcoe, ON MLS® S12172960

Residential Freehold (Detached)

$359000.0

Price drop by 5.5%

1 Beds
2 Baths
< 700 sq-ft

Welcome to this cute and cozy home located in Orillia's West Ward neighbourhood. This home has lots of natural light and plenty of potential for any f

23 Photos

132 Dunedin Street, Simcoe, ON , MLS #S12406088 , Image - 1

132 Dunedin Street Orillia, Simcoe, ON MLS® S12406088

Residential Freehold (Detached)

$299900.0

Price drop by 11.8%

2 Beds
1 Baths
< 700 sq-ft

Earn sweat equity. Perfect for a handyman. Steps to hospital, park, restaurants. Terrific starter for young ambitious couple. There is a garage but us

2 Photos

1366 Wilson Point Road, Simcoe, ON , MLS #S12369715 , Image - 1

1366 Wilson Point Road Orillia, Simcoe, ON MLS® S12369715

Residential Freehold (Vacant Land)

$280000.0

Attention builders or investors. A Beautiful, building lot in the City of Orillia. New city water and sewer services. Driveway permits pulled. Great

32 Photos

3 Courtland Street, Simcoe, ON , MLS #S12514032 , Image - 1

3 Courtland Street Orillia, Simcoe, ON MLS® S12514032

Residential Freehold (Detached)

$389000.0

2 Beds
1 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Zoned Village Commercial, this unique property offers endless flexibility to live comfortably, run a busines

14 Photos

267 Barrie Road, Simcoe, ON , MLS #S12456852 , Image - 1

267 Barrie Road Orillia, Simcoe, ON MLS® S12456852

Residential Freehold (Vacant Land)

$275000.0

9 Beds
< 700 sq-ft

Vacant Land FOR SALE! **SELLER FINANCING AVAILABLE** Fantastic Opportunity: Build A TRIPLEX On A Huge 1/4 Acre Lot. Great For Multi-Generational Famil

1 Photos

217 Atherley Drive Orillia, Simcoe, ON MLS® S12311275

Residential Freehold (Vacant Land)

$429999.0

Price drop by 14.0%

< 700 sq-ft

Premium Downtown Waterfront Building Lot with Approved Permits Ready to Build An exceptional opportunity to build a luxury side-by-side duplex in Ori

32 Photos

173 Barrie Road, Simcoe, ON , MLS #S12122130 , Image - 1

173 Barrie Road Orillia, Simcoe, ON MLS® S12122130

Residential Freehold (Detached)

$424999.0

Price drop by 9.6%

3 Beds
2 Baths
700-1100 sq-ft

Welcome to 173 Barrie Road, a wonderful 2 storey detached house on 50ft lot perfect for first-time buyers or investors, located in the heart of Orilli

2 Photos

LOT 24 CON 12 North Orillia N/A W, Simcoe, ON , MLS #S12138570 , Image - 1

LOT 24 CON 12 North Orillia N/A W Orillia, Simcoe, ON MLS® S12138570

Residential Freehold (Vacant Land)

$136900.0

< 700 sq-ft

Nestled in the heart of a serene and lush wooded area, this stunning parcel of land offers a rare opportunity to own a piece of untouched nature. Span

23 Photos

382 West Street N, Simcoe, ON , MLS #S12397748 , Image - 1

382 West Street N Orillia, Simcoe, ON MLS® S12397748

Residential Freehold (Detached)

$385000.0

2 Beds
1 Baths
700-1100 sq-ft

Attention Builders/Developers/Investors. This may be the development/investment property you've been looking for. Property is being sold primarily as

9 Photos

424 Forest Avenue S, Simcoe, ON , MLS #40752390 , Image - 1

424 Forest Avenue S Orillia, Simcoe, ON MLS® 40752390

Residential (Single Family Residence)

$300000

2 Beds
1 Baths
740 sq-ft

Welcome to 424 Forest Avenue South, a fantastic investment opportunity in Orillia. Situated on a generously sized lot in a quiet, established neighbou

33 Photos

441 Barrie Road, Simcoe, ON , MLS #40746697 , Image - 1

Unit-54, 441 Barrie Road Orillia, Simcoe, ON MLS® 40746697

Residential (Row/Townhouse)

$440000

3 Beds
2 Baths
1356 sq-ft

Welcome to Orillia Woodlands, where you’ll find easy living in this tastefully updated condo townhouse, ideally located in Orillia with quick access t

22 Photos

132 Dunedin Street, Simcoe, ON , MLS #40741218 , Image - 1

132 Dunedin Street Orillia, Simcoe, ON MLS® 40741218

Residential (Single Family Residence)

$399900

2 Beds
1 Baths
596 sq-ft

Earn sweat equity. Perfect for a handyman. Steps to hospital, park, resturants. Terrific starter for young ambitious couple. There is a garage but use

27 Photos

83 Andrew Street S, Simcoe, ON , MLS #40735223 , Image - 1

83 Andrew Street S Orillia, Simcoe, ON MLS® 40735223

Residential (Single Family Residence)

$469000

Price drop by 2.3%

3 Beds
2 Baths
1350 sq-ft

Welcome to 83 Andrew Street S – A Move-In Ready Gem in the Heart of Orillia. As you drive in, you'll find ample parking as well as a single car garage

4 Photos

221 Matchedash Street S, Simcoe, ON , MLS #40724434 , Image - 1

221 Matchedash Street S Orillia, Simcoe, ON MLS® 40724434

Land (Residential)

$285000

Attention builders and investors! Vacant land for sale, corner lot on a quiet street. Building permit is ready and paid for. Fantastic opportunity to

2 Photos

147 Dufferin Street, Simcoe, ON , MLS #40680343 , Image - 1

147 Dufferin Street Orillia, Simcoe, ON MLS® 40680343

Residential (Single Family Residence)

$380000

Price drop by 9.3%

1 Beds
2 Baths
700 sq-ft

Welcome to this cute and cozy home located in Orillia's West Ward neighbourhood. This home has lots of natural light andplenty of potential for any fi

10 Photos

102 Victoria Street, Simcoe, ON , MLS #40693296 , Image - 1

102 Victoria Street Orillia, Simcoe, ON MLS® 40693296

Residential (Single Family Residence)

$339900

3 Beds
1 Baths
830 sq-ft

Attention First-Time Homebuyers, Investors, and Home Renovators!This charming 3-bedroom, 1-bathroom home sits on a 37 x 89 ft lot and offers fantastic

23 Photos

1095 Mississaga Street, Simcoe, ON , MLS #40668724 , Image - 1

Unit-77, 1095 Mississaga Street Orillia, Simcoe, ON MLS® 40668724

Residential (Row/Townhouse)

$436000

3 Beds
1 Baths
1078 sq-ft

Situated in a desirable neighborhood, this 3 bedroom townhome is perfect for first time buyers, downsizers and families. Newer kitchen with newer appl

20 Photos

325 West Street, Simcoe, ON , MLS #40681848 , Image - 1

Unit-13, 325 West Street Orillia, Simcoe, ON MLS® 40681848

Residential (Row/Townhouse)

$394900

3 Beds
2 Baths
1070 sq-ft

This end unit townhome, located in the desirable North Ward of Orillia, offers both convenience and comfort. Step inside to discover a welcoming layou

25 Photos

441 Barrie Road, Simcoe, ON , MLS #40675322 , Image - 1

Unit-34, 441 Barrie Road Orillia, Simcoe, ON MLS® 40675322

Residential (Row/Townhouse)

$459900

3 Beds
2 Baths
1160 sq-ft

This charming, affordable townhouse is a great opportunity for first-time buyers, downsizers, or investors. With 1160 sq. ft. of living space plus a f

27 Photos

441 Barrie Road, Simcoe, ON , MLS #40674563 , Image - 1

Unit-7, 441 Barrie Road Orillia, Simcoe, ON MLS® 40674563

Residential (Row/Townhouse)

$499000

3 Beds
2 Baths
1175 sq-ft

Don’t miss this charming two-storey townhouse, perfect for first-time buyers or growing families! Located close to Highway 11, Schools, and plenty of

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