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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: September 27, 2026

6 Photos

103 Mississaga Street W, Simcoe, ON , MLS #S13832824 , Image - 1

103 Mississaga Street W Orillia, Simcoe, ON MLS® S13832824

Residential Freehold (Detached)

$294500.0

2 Beds
1 Baths
< 700 sq-ft

This starter bungalow offers up main floor living composed of 2 bedrooms, an upgraded full bath, galley style kitchen with newer cabinets and counter,

27 Photos

381 Forest Avenue S, Simcoe, ON , MLS #S13831684 , Image - 1

381 Forest Avenue S Orillia, Simcoe, ON MLS® S13831684

Residential Freehold (Detached)

$379900.0

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 381 Forest Avenue, South! This bright and cozy 3-bedroom, 1-bath bungalow is located in a peaceful and friendly neighbourhood. Bright and i

22 Photos

54 Fittons Road W, Simcoe, ON , MLS #S13780956 , Image - 1

Unit-202, 54 Fittons Road W Orillia, Simcoe, ON MLS® S13780956

Residential Condo & Other (Condo Apartment)

$279000.0

2 Beds
2 Baths
1000-1199 sq-ft

This is an excellent opportunity for those looking to enjoy a comfortable, low-maintenance lifestyle in Orillia's popular North Ward. Everything you n

12 Photos

43 FITTONS Road W, Simcoe, ON , MLS #S13661072 , Image - 1

43 FITTONS Road W Orillia, Simcoe, ON MLS® S13661072

Residential Freehold (Detached)

$499999.0

4 +0 Beds
2 Baths
1500-2000 sq-ft

A unique opportunity at 43 Fittons Road West in Orillia, with options for today and exciting possibilities for the future. The existing home is full o

Open House : Sat Oct 03, 10:00 AM to 12:00 PM

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580 West Street S, Simcoe, ON , MLS #S13814274 , Image - 1

Unit-33, 580 West Street S Orillia, Simcoe, ON MLS® S13814274

Residential Freehold (MobileTrailer)

$209900.0

3 Beds
1 Baths
1100-1500 sq-ft

Renovated three-bedroom in Lakeside Estates with the big-ticket items already handled. A high-efficiency gas furnace and central air system were both

34 Photos

67 Fittons Road E, Simcoe, ON , MLS #S13829864 , Image - 1

Unit-18, 67 Fittons Road E Orillia, Simcoe, ON MLS® S13829864

Residential Condo & Other (Condo Townhouse)

$379900.0

4 Beds
2 Baths
1200-1399 sq-ft

Discover an exceptional opportunity for first-time buyers, investors, or those looking to downsize into low-maintenance living. Ideally situated in th

23 Photos

356 West Street N, Simcoe, ON , MLS #S13686360 , Image - 1

356 West Street N Orillia, Simcoe, ON MLS® S13686360

Residential Freehold (Detached)

$449900.0

4 Beds
1 Baths
1100-1500 sq-ft

Welcome to 356 West St N in Orillia's desirable North Ward. This affordable four-bedroom home offers plenty of space for families, first-timebuyers, o

28 Photos

148 Coldwater Road W, Simcoe, ON , MLS #S13789516 , Image - 1

148 Coldwater Road W Orillia, Simcoe, ON MLS® S13789516

Residential Freehold (Detached)

$449999.0

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to 148 Coldwater Rd W. Excellent location with amenities at your fingertips & Victoria Park down the street. Endless potential awaits in thi

1 Photos

217 Atherley Road Orillia, Simcoe, ON MLS® S13819366

Residential Freehold (Vacant Land)

$299999.0

PREMIUM DOWNTOWN WATERFRONT AREA BUIDING LOT. PERMIT APPROVED AND READY TO BUILD SIDE BY SIDELUXURY DUPLEX OVER 4000 SQ FT ON THREE LEVELS PLUS LEGAL

16 Photos

239 Front Street S, Simcoe, ON , MLS #S13619760 , Image - 1

239 Front Street S Orillia, Simcoe, ON MLS® S13619760

Residential Freehold (Detached)

$374900.0

Price drop by 6.0%

2 +0 Beds
1 Baths
700-1100 sq-ft

Incredible Investment Opportunity & Modern Turn-Key Home in the Heart of Orillia. Welcome to this beautifully updated 2-bedroom, 1-bathroom detached h

9 Photos

166 Laclie Street, Simcoe, ON , MLS #S13224634 , Image - 1

166 Laclie Street Orillia, Simcoe, ON MLS® S13224634

Residential Freehold (Detached)

$359000.0

Price drop by 28.1%

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

Not every opportunity comes wrapped in fresh paint and granite countertops. Some come with vision. Located in Orillia's desirable North Ward and just

21 Photos

800 West Ridge Boulevard, Simcoe, ON , MLS #S13798050 , Image - 1

Unit-125, 800 West Ridge Boulevard Orillia, Simcoe, ON MLS® S13798050

Residential Freehold (Att/Row/Townhouse)

$419999.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome to this beautifully 3-bedroom, 3-bathroom end-unit townhome, offering a bright, spacious, and inviting layout. Featuring an open-concept desig

46 Photos

25 Simcoe Street, Simcoe, ON , MLS #S13684472 , Image - 1

25 Simcoe Street Orillia, Simcoe, ON MLS® S13684472

Residential Freehold (Detached)

$499999.0

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

Welcome to this gem, a beautifully updated 3+2 bedroom bungalow offering the perfect blend of comfort, style and functionality. Step inside to discove

38 Photos

441 Barrie Road, Simcoe, ON , MLS #S13710244 , Image - 1

Unit-16, 441 Barrie Road Orillia, Simcoe, ON MLS® S13710244

Residential Condo & Other (Condo Townhouse)

$359900.0

Price drop by 2.7%

3 Beds
2 Baths
1000-1199 sq-ft

Well cared for and tastefully updated two-storey townhouse situated in the highly desirable Orillia Woodlands Condominium community. This inviting thr

40 Photos

345 LINWOOD Avenue, Simcoe, ON , MLS #S13810206 , Image - 1

345 LINWOOD Avenue Orillia, Simcoe, ON MLS® S13810206

Residential Freehold (Detached)

$449400.0

5 +1 Beds
3 Baths
1100-1500 sq-ft

Opportunity awaits in this detached 1-storey family home located on a quiet residential street in south-central Orillia. Situated on a standard-sized

45 Photos

275 Nottawasaga Street, Simcoe, ON , MLS #S13791566 , Image - 1

275 Nottawasaga Street Orillia, Simcoe, ON MLS® S13791566

Residential Freehold (Detached)

$499900.0

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

Welcome home to this inviting raised bungalow in the heart of Orillia! Offering a wonderful blend of comfort, space, and convenience, this thoughtfull

12 Photos

167 Laclie Street, Simcoe, ON , MLS #S13794736 , Image - 1

167 Laclie Street Orillia, Simcoe, ON MLS® S13794736

Residential Freehold (Detached)

$369000.0

1 Beds
1 Baths
700-1100 sq-ft

Welcome to 167 Laclie St, Orillia - a well-located property offering flexibility, recent improvements and exciting value-add potential. Set in an esta

8 Photos

600 West Street S, Simcoe, ON , MLS #S13561268 , Image - 1

600 West Street S Orillia, Simcoe, ON MLS® S13561268

Residential Freehold (Detached)

$349000.0

Price drop by 12.5%

2 Beds
1 Baths
700-1100 sq-ft

Attention Builders, Renovators, & Investors! Exceptional opportunity in the highly sought-after Lakeside Estates community. Situated in Orillia's desi

8 Photos

50 DUNEDIN Street, Simcoe, ON , MLS #S13440270 , Image - 1

50 DUNEDIN Street Orillia, Simcoe, ON MLS® S13440270

Residential Freehold (Detached)

$399000.0

3 Beds
1 Baths
700-1100 sq-ft

The property includes an approximately 1,100 sq. ft. house currently rented for $950 per month plus utilities and is in poor condition. The house has

50 Photos

8 Dunn Avenue, Simcoe, ON , MLS #S13791572 , Image - 1

8 Dunn Avenue Orillia, Simcoe, ON MLS® S13791572

Residential Freehold (Detached)

$459900.0

2 Beds
1 Baths
700-1100 sq-ft

This charming West Ward bungalow is proof that great things come in small packages! Set on a surprisingly deep, private lot surrounded by mature trees

4 Photos

79 Frederick Street, Simcoe, ON , MLS #S13655208 , Image - 1

79 Frederick Street Orillia, Simcoe, ON MLS® S13655208

Residential Freehold (Detached)

$399900.0

Price drop by 19.9%

3 Beds
1 Baths
1100-1500 sq-ft

ESTATE SALE - A Rare Opportunity in the Heart of Historic Orillia! Offered for the first time in generations, this cherished family home was lovingly

35 Photos

87 Bond Street, Simcoe, ON , MLS #S13672502 , Image - 1

87 Bond Street Orillia, Simcoe, ON MLS® S13672502

Residential Freehold (Detached)

$499000.0

Price drop by 3.9%

4 +0 Beds
2 Baths
1100-1500 sq-ft

Investors, contractors, handyman and families this property offers plenty of potential on a large lot 60' x 239'. House is a 1 1/2 storey approx 1442

25 Photos

531 High Street, Simcoe, ON , MLS #S13780498 , Image - 1

Unit-9, 531 High Street Orillia, Simcoe, ON MLS® S13780498

Residential Condo & Other (Condo Townhouse)

$314500.0

3 Beds
2 Baths
1000-1199 sq-ft

Are you searching for an affordable home/condo that requires little maintenance and has no elevators? This is your opportunity! This condo townhome fe

19 Photos

331 Linwood Avenue, Simcoe, ON , MLS #S13780420 , Image - 1

331 Linwood Avenue Orillia, Simcoe, ON MLS® S13780420

Residential Freehold (Detached)

$499900.0

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to this charming 3-bedroom, 1.5-storey home nestled in a great family-friendly neighbourhood in Orillia! Featuring neutral décor throughout, t

17 Photos

107 Bond Street, Simcoe, ON , MLS #S13512384 , Image - 1

Unit-208, 107 Bond Street Orillia, Simcoe, ON MLS® S13512384

Residential Condo & Other (Condo Apartment)

$319900.0

2 Beds
1 Baths
700-799 sq-ft

Bright and freshly painted 2-bedroom, 1-bathroom condo in Orillia, located on the second floor.This well-designed unit features a functional layout, h

21 Photos

486 Laclie Street, Simcoe, ON , MLS #S13772916 , Image - 1

Unit-Unit 111, 486 Laclie Street Orillia, Simcoe, ON MLS® S13772916

Residential Condo & Other (Condo Apartment)

$439900.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to Maple Arbour Condominiums, one of Orillia's most sought-after communities. This bright and spacious ground-floor unit offers convenient, lo

23 Photos

345 East Street, Simcoe, ON , MLS #S13696788 , Image - 1

345 East Street Orillia, Simcoe, ON MLS® S13696788

Residential Freehold (Detached)

$424000.0

Price drop by 3.4%

2 Beds
1 Baths
700-1100 sq-ft

A detached home in an established Orillia neighbourhood, offered under $450,000. A rare entry point into the market at this price, with room to add yo

19 Photos

10 First Street, Simcoe, ON , MLS #S13736770 , Image - 1

10 First Street Orillia, Simcoe, ON MLS® S13736770

Residential Freehold (Vacant Land)

$294500.0

< 700 sq-ft

Approved Engineered Drawings For A Duplex. Prime R2 Lot In Orillia's Desirable North Ward. Multi Unit Residential Lot Offering Outstanding Development

50 Photos

12 LANKIN Boulevard, Simcoe, ON , MLS #S13481748 , Image - 1

Unit-#22, 12 LANKIN Boulevard Orillia, Simcoe, ON MLS® S13481748

Residential Condo & Other (Condo Townhouse)

$408000.0

Price drop by 2.8%

3 +0 Beds
1 Baths
1200-1399 sq-ft

Experience lakeside living in this fully renovated, multi-level condo townhouse just a few hundred yards from Lake Simcoe. Unit 22, 12 Lankin Blvd, si

14 Photos

93 Bond Street, Simcoe, ON , MLS #S13752114 , Image - 1

93 Bond Street Orillia, Simcoe, ON MLS® S13752114

Residential Freehold (Detached)

$399900.0

1 Beds
1 Baths
< 700 sq-ft

COZY BUNGALOW WITH TASTEFUL FINISHES ON A 239-FT-DEEP LOT, A DETACHED OUTBUILDING & A PRIME ORILLIA LOCATION! The backyard stretches far beyond the ho

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