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Houses for Sale in Orillia ON Under $5 Million - P9

Showing results 241 - 261 of 261
Last Updated: August 06, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
32 Photos
Last Updated : 77 Days ago
25 SKYLINE Drive, Simcoe, ON , MLS #S13132656 , Image - 1
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25 SKYLINE Drive Orillia, Simcoe, ON MLS® S13132656

Residential Freehold (Detached)

$599900.0
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 25 Skyline Dr in Orillia's desirable North Ward. This bungalow features a 3-bedroom main floor, a cozy living space filled with natural lig
1 Photos
Last Updated : 83 Days ago
263 Canice Street, Simcoe, ON
263 Canice Street Orillia, Simcoe, ON MLS® S13075776

Residential Freehold (Multiplex)

$2599000.0
  • 12 Beds
  • 12 Baths
  • 2500-3000 sq-ft
Incredible investment opportunity in Orillia. Fully occupied 12-unit apartment building with stable income from day one.The property generates approxi
21 Photos
Last Updated : 83 Days ago
423 Mary Street, Simcoe, ON , MLS #S13134834 , Image - 1

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423 Mary Street Orillia, Simcoe, ON MLS® S13134834

Residential Freehold (Detached)

$595000.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
CORNER LOT SIDESPLIT WITH BIG-TICKET UPDATES, A BACKYARD BUNKIE, FINISHED BASEMENT & OVERSIZED GARAGE! 423 Mary Street starts strong where buyers tend
46 Photos
Last Updated : 83 Days ago
201 Cedar Island Road, Simcoe, ON , MLS #S12151443 , Image - 1

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201 Cedar Island Road Orillia, Simcoe, ON MLS® S12151443

Residential Freehold (Detached)

$2599900.0
  • 3 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Tucked along a quiet bay on Lake Couchiching, this stunning waterfront cottage or year-round home offers the peaceful lifestyle you've been dreaming o
34 Photos
Last Updated : 85 Days ago
140 Cedar Island Road, Simcoe, ON , MLS #S13120086 , Image - 1

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Unit-311, 140 Cedar Island Road Orillia, Simcoe, ON MLS® S13120086

Residential Condo & Other (Condo Apartment)

$648700.0
  • 2 +0 Beds
  • 2 Baths
  • 1200-1399 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
24 Photos
Last Updated : 86 Days ago
28 rose Avenue, Simcoe, ON , MLS #S13116276 , Image - 1

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28 rose Avenue Orillia, Simcoe, ON MLS® S13116276

Residential Freehold (Semi-Detached )

$659900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Featuring soaring 9-foot ceilings, oversized windows, and premium wide-plank vinyl flooring throughout, this modern luxury residence offers exceptiona
2 Photos
Last Updated : 86 Days ago
LOT 24 CON 12 North Orillia N/A W, Simcoe, ON , MLS #S13115956 , Image - 1
LOT 24 CON 12 North Orillia N/A W Orillia, Simcoe, ON MLS® S13115956

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
42 Photos
Last Updated : 90 Days ago
67 Wyn Wood Lane, Simcoe, ON , MLS #S13075484 , Image - 1

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67 Wyn Wood Lane Orillia, Simcoe, ON MLS® S13075484

Residential Freehold (Att/Row/Townhouse)

$989000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Life by the lake! Stunning corner unit freehold townhome in the heart of Downtown Orillia literally STEPS to the beautiful LAKE! This 3 Bedroom home b
11 Photos
Last Updated : 90 Days ago
385 Mary Street, Simcoe, ON , MLS #S13101284 , Image - 1

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385 Mary Street Orillia, Simcoe, ON MLS® S13101284

Residential Freehold (Detached)

$425000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordability in Orillia's West Ward. Featuring Two Bedroom Bungalow on a Large Corner Lot with Detached Garage. Featuring Metal Roof, Newer Windows,
20 Photos
Last Updated : 91 Days ago
102 Dunlop Street, Simcoe, ON , MLS #S13085964 , Image - 1

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102 Dunlop Street Orillia, Simcoe, ON MLS® S13085964

Residential Freehold (Triplex)

$799900.0
  • 8 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Well built 3 unit building. Lower 2 bedroom unit rents for $1650 monthly, main floor unit rents for $1800 monthly, upper 3 bedroom currently vacant. T
42 Photos
Last Updated : 93 Days ago
3063 Stone Ridge Boulevard, Simcoe, ON , MLS #S13084030 , Image - 1

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3063 Stone Ridge Boulevard Orillia, Simcoe, ON MLS® S13084030

Residential Freehold (Detached)

$1149000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Sprawling custom-built family bungalow showcasing a bright open-concept layout with high-end finishes throug
13 Photos
Last Updated : 93 Days ago
454 Bay Street, Simcoe, ON , MLS #S13045272 , Image - 1

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454 Bay Street Orillia, Simcoe, ON MLS® S13045272

Residential Freehold (Vacant Land)

$499900.0
Rare opportunity to build your dream home on a private, mature lot in Orillia's desirable North Ward. This partially cleared 100 x 200 ft property bac
38 Photos
Last Updated : 94 Days ago
235 Canice Street, Simcoe, ON , MLS #S12994258 , Image - 1

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235 Canice Street Orillia, Simcoe, ON MLS® S12994258

Residential Freehold (Multiplex)

$2299000.0
  • 8 +4 Beds
  • 7 Baths
  • 3500-5000 sq-ft
Exceptional opportunity to own a fully renovated 7-unit apartment building with high in-place income and excellent tenant profile. Completely occupied
5 Photos
Last Updated : 98 Days ago
463 Atherley Road, Simcoe, ON , MLS #S12966858 , Image - 1
463 Atherley Road Orillia, Simcoe, ON MLS® S12966858

Residential Freehold (Vacant Land)

$450000.0
23 Photos
Last Updated : 99 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)

$375000.0
  • 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
50 Photos
Last Updated : 99 Days ago
3068 Emperor Drive, Simcoe, ON , MLS #S13057022 , Image - 1

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3068 Emperor Drive Orillia, Simcoe, ON MLS® S13057022

Residential Freehold (Detached)

$849900.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 3068 Emperor Drive, located in one of Orillia's most desirable family neighbourhoods. Set on a quiet, tree-lined street, this spacious 4-be
1 Photos
Last Updated : 101 Days ago
66 Neywash Street, Simcoe, ON
66 Neywash Street Orillia, Simcoe, ON MLS® S12821260

Residential Freehold (Multiplex)

$3550000.0
price drop iconPrice drop by 5.3%
  • 18 Beds
  • 13 Baths
  • 5000 + sq-ft
Stately Built Brick Multi 12 Plex in Prime Downtown Orillia. 12 Units plus Owners Bachelor Unit. Consists of 7 one bedroom apartments, 4 two bedroom
29 Photos
Last Updated : 104 Days ago
177 Shannon Street, Simcoe, ON , MLS #S13039084 , Image - 1

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177 Shannon Street Orillia, Simcoe, ON MLS® S13039084

Residential Freehold (Detached)

$650000.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 177 Shannon Street in Orillia-an opportunity to own a beautifully maintained raised bungalow in a location that truly checks every box. Thi
40 Photos
Last Updated : 114 Days ago
345 LINWOOD Avenue, Simcoe, ON , MLS #S12994782 , Image - 1

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345 LINWOOD Avenue Orillia, Simcoe, ON MLS® S12994782

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
37 Photos
Last Updated : 119 Days ago
48 Wyn Wood Lane, Simcoe, ON , MLS #S12973708 , Image - 1

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48 Wyn Wood Lane Orillia, Simcoe, ON MLS® S12973708

Residential Freehold (Att/Row/Townhouse)

$1100000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to Premium Water-View Living at Its Best! This stunning, newly built 3-storey townhome is situated in the exclusive Orillia Fresh community, o
5 Photos
Last Updated : 150 Days ago
136 Barrie Road, Simcoe, ON , MLS #S12856768 , Image - 1
136 Barrie Road Orillia, Simcoe, ON MLS® S12856768

Residential Freehold (Duplex)

$499999.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Check out this outstanding investment opportunity featuring zoning and permitted use information available in the documents section. This legal duplex
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