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Houses for Sale in Orillia ON Under $5 Million

Showing results 1 - 30 of 224

Are you looking for houses under $5m 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 $5m 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 $5m, including freehold homes, condos, and commercial properties.

Last Updated: November 07, 2026

45 Photos

32 Carter Crescent, Simcoe, ON , MLS #S13810230 , Image - 1

32 Carter Crescent Orillia, Simcoe, ON MLS® S13810230

Residential Freehold (Detached)

$745000.0

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

Well-kept, all-brick bungalow in Orillia's sought-after Rynard Estates, offering a comfortable floor plan, generous finished living space and a privat

18 Photos

296 Crawford Street, Simcoe, ON , MLS #S14159002 , Image - 1

296 Crawford Street Orillia, Simcoe, ON MLS® S14159002

Residential Freehold (Detached)

$549000.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to this 3 bedroom, 1 bathroom home in a quiet, family friendly neighbourhood with easy access to the Highway 12 by-pass and Highway 11. Oversi

35 Photos

12 Lankin Boulevard, Simcoe, ON , MLS #S14094722 , Image - 1

Unit-12, 12 Lankin Boulevard Orillia, Simcoe, ON MLS® S14094722

Residential Condo & Other (Condo Townhouse)

$374990.0

3 Beds
1 Baths
1000-1199 sq-ft

Freshly updated and move-in ready, this bright 3-bedroom condo townhouse offers outstanding value in a well-managed Orillia community. Featuring a fre

21 Photos

109 Albert Street S, Simcoe, ON , MLS #S14158158 , Image - 1

109 Albert Street S Orillia, Simcoe, ON MLS® S14158158

Residential Freehold (Triplex)

$699900.0

6 Beds
3 Baths
1500-2000 sq-ft

This beautifully updated 100+ year old home offers a rare opportunity with three self-contained residential units including a detached garden suite ap

28 Photos

148 Coldwater Road W, Simcoe, ON , MLS #S14099924 , Image - 1

148 Coldwater Road W Orillia, Simcoe, ON MLS® S14099924

Residential Freehold (Detached)

$369000.0

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 inthis s

Open House : Sat Nov 14, 02:00 PM to 04:00 PM

34 Photos

1095 Mississaga Street W, Simcoe, ON , MLS #S14142642 , Image - 1

Unit-121, 1095 Mississaga Street W Orillia, Simcoe, ON MLS® S14142642

Residential Condo & Other (Condo Townhouse)

$389900.0

3 Beds
2 Baths
900-999 sq-ft

Welcome to 1095 Mississaga Street W., Unit 121, a bright and well-maintained end-unit townhome offering comfort, convenience, and exceptional value in

48 Photos

265 Diana Drive, Simcoe, ON , MLS #S14157380 , Image - 1

265 Diana Drive Orillia, Simcoe, ON MLS® S14157380

Residential Freehold (Detached)

$894900.0

4 Beds
4 Baths
2000-2500 sq-ft

One-Of-A-Kind & Move-In Ready! You Won't Want To Miss Your Opportunity To Own This Rare Offering In The Highly Sought After Community Of Westridge.

45 Photos

64 Vanessa Drive, Simcoe, ON , MLS #S13696376 , Image - 1

64 Vanessa Drive Orillia, Simcoe, ON MLS® S13696376

Residential Freehold (Detached)

$649900.0

Price drop by 8.5%

3 Beds
3 Baths
1100-1500 sq-ft

Beautifully finished and move-in ready, this 3-bedroom, 3-bathroom home is located in Orillia's popular West Ridge community. Bright and airy, it offe

34 Photos

383 High Street, Simcoe, ON , MLS #S14112002 , Image - 1

383 High Street Orillia, Simcoe, ON MLS® S14112002

Residential Freehold (Detached)

$529900.0

6 Beds
2 Baths
1100-1500 sq-ft

Raised bungalow 1152 Square feet 3+3 bedrooms. Two kitchens two bathrooms. Few updates plumbing, electrical, most fixtures are original. A seniors

45 Photos

54 Wyandotte Street, Simcoe, ON , MLS #S14154242 , Image - 1

54 Wyandotte Street Orillia, Simcoe, ON MLS® S14154242

Residential Freehold (Duplex)

$499900.0

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

Welcome to this updated legal duplex located in an extremely convenient location, just a short walk to the hospital and downtown Orillia! Offering tw

32 Photos

535 High Street N, Simcoe, ON , MLS #S14155156 , Image - 1

535 High Street N Orillia, Simcoe, ON MLS® S14155156

Residential Freehold (Detached)

$639900.0

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

Where VINTAGE CHARM meets MODERN LUXURY - Welcome to 535 High Street - from the moment you arrive you will be captivated by the stunning curb appeal o

Open House : Sat Nov 14, 12:00 PM to 02:00 PM

30 Photos

12 Francis Road, Simcoe, ON , MLS #S13549548 , Image - 1

12 Francis Road Orillia, Simcoe, ON MLS® S13549548

Residential Freehold (Detached)

$1079900.0

3 Beds
2 Baths
1100-1500 sq-ft

What makes a property truly rare? A beautifully updated, move-in-ready home on an exceptional mature lot in one of Orillia's most sought-after neighbo

Open House : Sat Nov 07, 11:00 AM to 01:00 PM

50 Photos

1 Mariners Pier Way, Simcoe, ON , MLS #S14146206 , Image - 1

1 Mariners Pier Way Orillia, Simcoe, ON MLS® S14146206

Residential Freehold (Att/Row/Townhouse)

$739950.0

3 Beds
3 Baths
1500-2000 sq-ft

YOUR HOME. YOUR COTTAGE. YOUR WATERFRONT ESCAPE. Welcome to an incredible opportunity to bring your home, cottage and love of the water together for u

20 Photos

233 West Street N, Simcoe, ON , MLS #S14133180 , Image - 1

233 West Street N Orillia, Simcoe, ON MLS® S14133180

Residential Freehold (Detached)

$549000.0

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

One Property, Endless Possibilities! Discover an exceptional opportunity in Orillia with this detached raised bungalow offering two self-contained res

32 Photos

424 Homewood Avenue, Simcoe, ON , MLS #S13610426 , Image - 1

424 Homewood Avenue Orillia, Simcoe, ON MLS® S13610426

Residential Freehold (Detached)

$649900.0

Price drop by 16.1%

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

Welcome to 424 Homewood located in Orillia, this exceptional property offers a rare combination of spacious living and private outdoor space on a doub

49 Photos

10 Invermara Court, Simcoe, ON , MLS #S13846104 , Image - 1

Unit-36, 10 Invermara Court Orillia, Simcoe, ON MLS® S13846104

Residential Freehold (Detached)

$949000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to 10 - 36 Invermara Court a stunning bungaloft nestled within the exclusive gated waterfront community of Sophie's Landing on the shores of L

48 Photos

174 Barrie Road, Simcoe, ON , MLS #S14151422 , Image - 1

174 Barrie Road Orillia, Simcoe, ON MLS® S14151422

Residential Freehold (Duplex)

$439900.0

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

The Price is Right!!! This legal 2-unit home (duplex) sits on an exceptionally deep lot (46.42ft x 196.66ft x 40.29ft x 173.19ft) just off Memorial Dr

45 Photos

800 West Ridge Boulevard, Simcoe, ON , MLS #S14108886 , Image - 1

Unit-32, 800 West Ridge Boulevard Orillia, Simcoe, ON MLS® S14108886

Residential Freehold (Att/Row/Townhouse)

$530000.0

Price drop by 3.6%

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to this bright and beautifully maintained 3-bedroom, 4-washroom townhome in Orillia's sought-after Westridge community! One of the larger unit

12 Photos

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

167 Laclie Street Orillia, Simcoe, ON MLS® S13794736

Residential Freehold (Detached)

$329900.0

Price drop by 10.6%

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

1 Photos

69 Olive Crescent Orillia, Simcoe, ON MLS® S14125460

Residential Freehold (Detached)

$800000.0

3 +0 Beds
1 Baths
700-1100 sq-ft

Updated, turnkey Lake Simcoe waterfront with municipal water, sewer and year-round access on a municipal road-no well or septic to maintain! Boat thro

30 Photos

37 Toboggan Hill Drive, Simcoe, ON , MLS #S14031846 , Image - 1

37 Toboggan Hill Drive Orillia, Simcoe, ON MLS® S14031846

Residential Freehold (Detached)

$649900.0

Price drop by 4.4%

3 +0 Beds
2 Baths
1100-1500 sq-ft

Welcome to 37 Toboggan Hill Drive, an immaculately maintained home on one of Orillia's most highly desired streets. Recent updates include a newer roo

Open House : Sun Nov 08, 12:30 PM to 02:00 PM

41 Photos

68 CINDY LEE Crescent, Simcoe, ON , MLS #S14107618 , Image - 1

68 CINDY LEE Crescent Orillia, Simcoe, ON MLS® S14107618

Residential Freehold (Detached)

$599000.0

Price drop by 2.6%

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

WELCOME TO 68 CINDY LEE CRESCENT - 5 BEDROOMS, 2 KITCHENS & IMPRESSIVE UPGRADES! Located on a quiet crescent in Orillia's established West Ward, this

Open House : Sun Nov 08, 12:30 PM to 03:00 PM

37 Photos

46 Michelle Drive, Simcoe, ON , MLS #S14148224 , Image - 1

46 Michelle Drive Orillia, Simcoe, ON MLS® S14148224

Residential Freehold (Att/Row/Townhouse)

$550000.0

3 Beds
3 Baths
1100-1500 sq-ft

The Location You'll Love. Welcome to this beautifully maintained end-unit townhouse in a sought-after, convenient Orillia location! Offering over 1,50

49 Photos

140 Cedar Island Road, Simcoe, ON , MLS #S13733332 , Image - 1

Unit-109, 140 Cedar Island Road Orillia, Simcoe, ON MLS® S13733332

Residential Condo & Other (Condo Apartment)

$687000.0

2 Beds
2 Baths
1400-1599 sq-ft

Wake up to breathtaking, unobstructed views of Lake Couchiching from the comfort of your own home at the highly sought-after Elgin Bay Club. Perfectly

Open House : Sun Nov 08, 01:00 PM to 03:00 PM

49 Photos

531 High Street, Simcoe, ON , MLS #S14087034 , Image - 1

Unit-18, 531 High Street Orillia, Simcoe, ON MLS® S14087034

Residential Condo & Other (Condo Townhouse)

$319500.0

3 Beds
2 Baths
1000-1199 sq-ft

Looking for an affordable entry into the real estate market or an opportunity to simplify your lifestyle? Welcome to 18-531 High Street in Orillia! Th

34 Photos

140 Cedar Island Road, Simcoe, ON , MLS #S14113014 , Image - 1

Unit-311, 140 Cedar Island Road Orillia, Simcoe, ON MLS® S14113014

Residential Condo & Other (Condo Apartment)

$498700.0

2 +0 Beds
2 Baths
1000-1199 sq-ft

Welcome to Unit 311 at the prestigious Elgin Bay Club - one of Orillia's most desirable waterfront condominium communities. This spacious and beautifu

Open House : Sun Nov 08, 01:00 PM to 03:00 PM

50 Photos

15 Walker Avenue, Simcoe, ON , MLS #S14144196 , Image - 1

15 Walker Avenue Orillia, Simcoe, ON MLS® S14144196

Residential Freehold (Detached)

$599000.0

3 Beds
2 Baths
1100-1500 sq-ft

Completele remodelled, 2 storey 1150 sq ft brick and aluminum above grade home with 27' x 10' carport, paved driveway, large 101.71' x 149.87' irregul

40 Photos

8 Vanessa Drive, Simcoe, ON , MLS #S14123398 , Image - 1

8 Vanessa Drive Orillia, Simcoe, ON MLS® S14123398

Residential Freehold (Detached)

$599900.0

2 Beds
1 Baths
1100-1500 sq-ft

Charming, inviting, and full of potential! Welcome to 8 Vanessa Drive in Orillia, a lovely 2-bedroom home with spaces to relax, entertain, and make yo

Open House : Sat Nov 07, 01:00 PM to 03:00 PM

46 Photos

28 Borland Street W, Simcoe, ON , MLS #S14146938 , Image - 1

28 Borland Street W Orillia, Simcoe, ON MLS® S14146938

Residential Freehold (Detached)

$599999.0

3 Beds
2 Baths
700-1100 sq-ft

Located in the North Ward of Orillia this brick bungalow sits on a fully fenced lot. Close to schools, downtown, shopping and transit. This charming b

Open House : Sat Nov 07, 12:00 PM to 03:00 PM

37 Photos

90 Orchard Point Road, Simcoe, ON , MLS #S14145670 , Image - 1

Unit-601, 90 Orchard Point Road Orillia, Simcoe, ON MLS® S14145670

Residential Condo & Other (Condo Apartment)

$714900.0

2 Beds
1 Baths
800-899 sq-ft

Experience luxury waterfront living at the prestigious Orchard Point Harbour on the picturesque shores of Lake Simcoe. This beautifully appointed full

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