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Houses for Sale in Orillia ON Under $5 Million - P5

Showing results 121 - 150 of 263
Last Updated: September 21, 2026
  • New Listings
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  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
50 Photos
Last Updated : 11 Days ago
12 LANKIN Boulevard, Simcoe, ON , MLS #S13481748 , Image - 1
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Unit-#22, 12 LANKIN Boulevard Orillia, Simcoe, ON MLS® S13481748

Residential Condo & Other (Condo Townhouse)

$408000.0
price drop iconPrice 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
48 Photos
Last Updated : 12 Days ago
25 Atlantis Drive, Simcoe, ON , MLS #S13763122 , Image - 1

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25 Atlantis Drive Orillia, Simcoe, ON MLS® S13763122

Residential Freehold (Detached)

$840000.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to 25 Atlantis Drive, a beautifully maintained home built in 2020, nestled in Orillia's highly sought-after West Ridge community. Set in one o
25 Photos
Last Updated : 12 Days ago
328 Colborne Street W, Simcoe, ON , MLS #S13733786 , Image - 1

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328 Colborne Street W Orillia, Simcoe, ON MLS® S13733786

Residential Freehold (Detached)

$529900.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 328 Colborne St W in Orillia-a charming 4-bedroom, 2-bathroom, 1.5-storey detached home offering a flexible layout, attached single-car gar
32 Photos
Last Updated : 12 Days ago
95 Matchedash Street N, Simcoe, ON , MLS #S13742958 , Image - 1

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Unit-202, 95 Matchedash Street N Orillia, Simcoe, ON MLS® S13742958

Residential Condo & Other (Condo Apartment)

$599000.0
  • 2 Beds
  • 2 Baths
  • 1800-1999 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Set on the second level, this bright and welcoming condo is enhanced by large windows that invite an abunda
39 Photos
Last Updated : 12 Days ago
60 Museum Drive, Simcoe, ON , MLS #S13759538 , Image - 1

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Unit-518, 60 Museum Drive Orillia, Simcoe, ON MLS® S13759538

Residential Condo & Other (Condo Townhouse)

$649000.0
  • 2 Beds
  • 3 Baths
  • 2000-2249 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Located in the sought-after adult lifestyle community of Leacock Village, this charming two bedroom, three
13 Photos
Last Updated : 12 Days ago
26 rose Avenue, Simcoe, ON , MLS #S13759346 , Image - 1

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26 rose Avenue Orillia, Simcoe, ON MLS® S13759346

Residential Freehold (Semi-Detached )

$659900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Modern luxury. Light, volume, and a kitchen that actually cooks.This residence is built around height and light: soaring 9-foot ceilings, oversized wi
21 Photos
Last Updated : 13 Days ago
35 Canterbury Circle, Simcoe, ON , MLS #S13722500 , Image - 1

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35 Canterbury Circle Orillia, Simcoe, ON MLS® S13722500

Residential Freehold (Link)

$655000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Beautifully maintained 2 bedroom, 2 bathroom bungalow on a quiet cul-de-sac in highly desired development by Landen Homes in 2012. Main floor features
14 Photos
Last Updated : 13 Days ago
3063 Emperor Drive, Simcoe, ON , MLS #S13756380 , Image - 1

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3063 Emperor Drive Orillia, Simcoe, ON MLS® S13756380

Residential Freehold (Detached)

$784900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Located in the heart of the highly sought-after West Ridge community in Orillia, this exceptional 4-bedroom, 2.5-bathroom home is a true show-stopper!
33 Photos
Last Updated : 13 Days ago
192 John Street, Simcoe, ON , MLS #S13751758 , Image - 1

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192 John Street Orillia, Simcoe, ON MLS® S13751758

Residential Freehold (Detached)

$774999.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Exceptional Quality and Value! A Worry Free, immaculate, well maintained century home. Renovated and restored creating the perfect blend of original
14 Photos
Last Updated : 13 Days ago
93 Bond Street, Simcoe, ON , MLS #S13752114 , Image - 1

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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
39 Photos
Last Updated : 13 Days ago
506 West Street S, Simcoe, ON , MLS #S13755396 , Image - 1

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506 West Street S Orillia, Simcoe, ON MLS® S13755396

Residential Freehold (Detached)

$639000.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 506 West Street South, Orillia! This beautifully fully renovated 1.5-storey home offers modern updates, comfortable living space, and an ex
43 Photos
Last Updated : 13 Days ago
90 Pearl Drive, Simcoe, ON , MLS #S13753364 , Image - 1

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90 Pearl Drive Orillia, Simcoe, ON MLS® S13753364

Residential Freehold (Detached)

$589900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to your next chapter-a stylish, sun-filled 2-storey home offering 1,692 sq ft of thoughtfully designed living space with 3 bedrooms and 2.5 ba
43 Photos
Last Updated : 13 Days ago
269 Cedarmere Road, Simcoe, ON , MLS #S13147574 , Image - 1

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269 Cedarmere Road Orillia, Simcoe, ON MLS® S13147574

Residential Freehold (Detached)

$1259000.0
price drop iconPrice drop by 2.4%
  • 3 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 269 Cedarmere Road, in one of Orillia's most desirable neighbourhoods, minutes from Lake Couchiching. This beautifully maintained home offe
15 Photos
Last Updated : 13 Days ago
3195 Orion Boulevard, Simcoe, ON , MLS #S13677548 , Image - 1

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3195 Orion Boulevard Orillia, Simcoe, ON MLS® S13677548

Residential Freehold (Detached)

$999900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Looking for a premier location close to schools, shopping, parks and trails? Looking for the quality of a custom built home without all the decisions
44 Photos
Last Updated : 13 Days ago
2 Vanessa Drive, Simcoe, ON , MLS #S13752982 , Image - 1

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2 Vanessa Drive Orillia, Simcoe, ON MLS® S13752982

Residential Freehold (Detached)

$999999.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Perfectly positioned in the heart of Orillia, this spacious legal duplex offers exceptional convenience, wal
31 Photos
Last Updated : 13 Days ago
396 Mary Street, Simcoe, ON , MLS #S13751738 , Image - 1

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396 Mary Street Orillia, Simcoe, ON MLS® S13751738

Residential Freehold (Detached)

$674999.0
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set in a welcoming, family-friendly neighbourhood and backing directly onto Homewood Park, this spacious fiv
14 Photos
Last Updated : 13 Days ago
267 Barrie Road, Simcoe, ON , MLS #S13234824 , Image - 1

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267 Barrie Road Orillia, Simcoe, ON MLS® S13234824

Residential Freehold (Vacant Land)

$225900.0
price drop iconPrice drop by 5.4%
Vacant Land For Sale! Seller Financing Available. A great opportunity to build on a large ~1/4 acre lot in a convenient downtown Orillia location.
44 Photos
Last Updated : 13 Days ago
743 Broadview Avenue, Simcoe, ON , MLS #S13751444 , Image - 1

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743 Broadview Avenue Orillia, Simcoe, ON MLS® S13751444

Residential Freehold (Detached)

$1299800.0
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Desirable Couchiching Point 86' WATERFRONT All-Year Round 2+2 Raised Detached Bungalow on Premium Lot. **Over 2,500 Sq Ft Of Living Space. Recently Re
6 Photos
Last Updated : 14 Days ago
3119 Emperor Drive, Simcoe, ON , MLS #S13723024 , Image - 1

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3119 Emperor Drive Orillia, Simcoe, ON MLS® S13723024

Residential Freehold (Detached)

$849000.0
  • 6 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Welcome to 3119 Emperor Drive, an extraordinary estate in Orillia's coveted Westridge community, where timeless elegance harmonizes with modern luxury
26 Photos
Last Updated : 14 Days ago
177 Atherley Road, Simcoe, ON , MLS #S13749246 , Image - 1

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177 Atherley Road Orillia, Simcoe, ON MLS® S13749246

Residential Freehold (Detached)

$399900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
DON'T JUDGE THIS BOOK BY ITS COVER - THE REAL STORY HERE MAY BE WHAT COMES NEXT! Whether you're looking for an affordable home, an income property or
41 Photos
Last Updated : 17 Days ago
354 Arthur Street, Simcoe, ON , MLS #S13745886 , Image - 1

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354 Arthur Street Orillia, Simcoe, ON MLS® S13745886

Residential Freehold (Detached)

$669000.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Well Here It Is!! Great Location and well maintained 2 storey home with 3 plus 1 bedrooms. Perfect family home close to amenities including hospital a
23 Photos
Last Updated : 17 Days ago
382 West Street N, Simcoe, ON , MLS #S13057842 , Image - 1

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382 West Street N Orillia, Simcoe, ON MLS® S13057842

Residential Freehold (Detached)

$350000.0
price drop iconPrice drop by 6.7%
  • 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
36 Photos
Last Updated : 17 Days ago
23A George Street, Simcoe, ON , MLS #S13110238 , Image - 1

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23A George Street Orillia, Simcoe, ON MLS® S13110238

Residential Freehold (Detached)

$599900.0
price drop iconPrice drop by 7.7%
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this well kept brick bungalow located in a family-friendly neighbourhood close to schools, parks, and everyday amenities. With no rear neig
37 Photos
Last Updated : 17 Days ago
46 Michelle Drive, Simcoe, ON , MLS #S13744744 , Image - 1

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46 Michelle Drive Orillia, Simcoe, ON MLS® S13744744

Residential Freehold (Att/Row/Townhouse)

$550000.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to this beautifully maintained end-unit townhouse offering over 1,500sq. ft. of finished living space in one of Orillia's most convenient loca
39 Photos
Last Updated : 17 Days ago
54 Fittons Road W, Simcoe, ON , MLS #S13591736 , Image - 1

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Unit-306, 54 Fittons Road W Orillia, Simcoe, ON MLS® S13591736

Residential Condo & Other (Condo Apartment)

$295000.0
price drop iconPrice drop by 7.8%
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to effortless condo living. This well maintained 2 bedroom, 2 bath condo unit in the north ward is move in ready. Whether you're looking to d
40 Photos
Last Updated : 18 Days ago
59 Wyn Wood Lane, Simcoe, ON , MLS #S13673206 , Image - 1

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59 Wyn Wood Lane Orillia, Simcoe, ON MLS® S13673206

Residential Freehold (Att/Row/Townhouse)

$564990.0
  • 2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
NEW CONSTRUCTION! HST REBATE IN EFFECT! FULL TARION NEW HOME WARRANTY! Welcome To 59 Wyn Wood In The Thriving Orillia Fresh Towns Community! Be The Fi
37 Photos
Last Updated : 18 Days ago
57 Wyn Wood Lane, Simcoe, ON , MLS #S13673224 , Image - 1

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57 Wyn Wood Lane Orillia, Simcoe, ON MLS® S13673224

Residential Freehold (Att/Row/Townhouse)

$569990.0
  • 2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
NEW CONSTRUCTION! HST REBATE IN EFFECT! FULL TARION NEW HOME WARRANTY! Welcome To 57 Wyn Wood In The Thriving Orillia Fresh Towns Community! Be The Fi
41 Photos
Last Updated : 18 Days ago
5 INVERMARA Court, Simcoe, ON , MLS #S13743234 , Image - 1

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Unit-49, 5 INVERMARA Court Orillia, Simcoe, ON MLS® S13743234

Residential Freehold (Detached)

$998000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 49-5 Invermara, a beautifully maintained 3+1 bedroom, 3-bathroom home in the sought-after waterfront community of Sophie's Landing. Residen
25 Photos
Last Updated : 18 Days ago
336 Forest Avenue N, Simcoe, ON , MLS #S13742100 , Image - 1

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336 Forest Avenue N Orillia, Simcoe, ON MLS® S13742100

Residential Freehold (Detached)

$499000.0
  • 3 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Great quiet location close to Lake Couchiching. Large 4 level side split with over 2100 square feet above grade with 3 plus 2 bedrooms. 2 decks of bac
32 Photos
Last Updated : 18 Days ago
115 Bond Street, Simcoe, ON , MLS #S13626036 , Image - 1

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Unit-Unit 201, 115 Bond Street Orillia, Simcoe, ON MLS® S13626036

Residential Condo & Other (Condo Apartment)

$315000.0
price drop iconPrice drop by 3.1%
  • 2 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Welcome to this Well-Maintained Condominium Complex offering comfort, convenience, and easy living. This spacious Two-Bedroom Corner Unit features a d
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