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Houses for Sale in Orillia ON Under $500K - P2

Showing results 31 - 60 of 68
Last Updated: August 13, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
29 Photos
Last Updated : 10 Days ago
26 South Street S, Simcoe, ON , MLS #S13606072 , Image - 1
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26 South Street S Orillia, Simcoe, ON MLS® S13606072

Residential Freehold (Detached)

$460000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 26 South Street, a move-in ready home located in Orillia's desirable North Ward. Situated on an oversized, fenced lot, this property offers
32 Photos
Last Updated : 12 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)

$325000.0
  • 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
43 Photos
Last Updated : 12 Days ago
232 Shannon Street, Simcoe, ON , MLS #S13511228 , Image - 1

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232 Shannon Street Orillia, Simcoe, ON MLS® S13511228

Residential Freehold (Detached)

$472500.0
price drop iconPrice drop by 5.5%
  • 2 +1 Beds
  • 3 Baths
  • 700-1100 sq-ft
Opportunity awaits at 232 Shannon Street in Orillia. This raised bungalow offers a practical layout with 2 bedrooms on the main level, 1 additional be
15 Photos
Last Updated : 13 Days ago
430 Gill Street, Simcoe, ON , MLS #S13620104 , Image - 1

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430 Gill Street Orillia, Simcoe, ON MLS® S13620104

Residential Freehold (Detached)

$419900.0
  • 1 Beds
  • 1 Baths
  • 700-1100 sq-ft
Perfect for first-time buyers or those looking to downsize, this well-maintained bungalow sits on a level, fully fenced lot and offers excellent value
18 Photos
Last Updated : 13 Days ago
408 Regent Street, Simcoe, ON , MLS #S13142828 , Image - 1

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408 Regent Street Orillia, Simcoe, ON MLS® S13142828

Residential Freehold (Detached)

$475000.0
price drop iconPrice drop by 4.8%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
AFFORDABLE FAMILY LIVING STEPS FROM ORILLIA'S BEST AMENITIES - BRIGHT, SPACIOUS, & READY TO GROW WITH YOU! Welcome to a bright and welcoming detached
12 Photos
Last Updated : 14 Days ago
105 Matchedash Street S, Simcoe, ON , MLS #S13620072 , Image - 1

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105 Matchedash Street S Orillia, Simcoe, ON MLS® S13620072

Residential Freehold (Vacant Land)

$349000.0
  • 5000 + sq-ft
Top 5 Reasons You Will Love This Property: 1) Situated on a 65'x105' corner lot at Matchedash Street South and Western Avenue, this property offers ou
16 Photos
Last Updated : 14 Days ago
239 Front Street S, Simcoe, ON , MLS #S13619760 , Image - 1

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

Residential Freehold (Detached)

$399000.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable Turnkey Detached Home In Orillia! This beautifully updated 2 bedroom 1 bathroom home is perfectly suited for first-time buyers, working pro
30 Photos
Last Updated : 14 Days ago
124 MARY Street, Simcoe, ON , MLS #S13591868 , Image - 1

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124 MARY Street Orillia, Simcoe, ON MLS® S13591868

Residential Freehold (Detached)

$449900.0
price drop iconPrice drop by 4.3%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to this charming bungalow, ideally located in an established neighbourhood just minutes from downtown Orillia, parks, shopping, restaurants, s
22 Photos
Last Updated : 15 Days ago
54 Fittons Road W, Simcoe, ON , MLS #S13615614 , Image - 1

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Unit-202, 54 Fittons Road W Orillia, Simcoe, ON MLS® S13615614

Residential Condo & Other (Condo Apartment)

$299900.0
  • 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 desirable North Ward. Everything you
29 Photos
Last Updated : 15 Days ago
325 West Street N, Simcoe, ON , MLS #S13453354 , Image - 1

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Unit-21, 325 West Street N Orillia, Simcoe, ON MLS® S13453354

Residential Condo & Other (Condo Townhouse)

$395000.0
price drop iconPrice drop by 2.5%
  • 3 +0 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Townhouse located in the North Ward with single car attached garage with large green space and parking. This end unit has been recently renovated wait
18 Photos
Last Updated : 20 Days ago
492 Laclie Street, Simcoe, ON , MLS #S13600902 , Image - 1

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Unit-14, 492 Laclie Street Orillia, Simcoe, ON MLS® S13600902

Residential Condo & Other (Condo Townhouse)

$374900.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to 492 Laclie Street, Unit 14. Ideally located just minutes from downtown and Highway 11, this home offers the perfect balance of convenience
46 Photos
Last Updated : 21 Days ago
441 Barrie Road, Simcoe, ON , MLS #S13509204 , Image - 1

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Unit-35, 441 Barrie Road Orillia, Simcoe, ON MLS® S13509204

Residential Condo & Other (Condo Townhouse)

$399900.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Affordable Homeownership in Orillia's Woodlands Community! This neat & tidy 3 Bedroom townhouse offers an excellent opportunity for first-time buyers,
7 Photos
Last Updated : 21 Days ago
1382 Wilson Point Road, Simcoe, ON , MLS #S12970742 , Image - 1

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1382 Wilson Point Road Orillia, Simcoe, ON MLS® S12970742

Residential Freehold (Vacant Land)

$289000.0
price drop iconPrice drop by 3.3%
Private vacant parcel located 400 m from Lake Couchiching, with just over 2 acres and nearly 500 ft of road frontage. A rare opportunity to build a cu
50 Photos
Last Updated : 23 Days ago
45 ALBERT Street N, Simcoe, ON , MLS #S13551244 , Image - 1

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45 ALBERT Street N Orillia, Simcoe, ON MLS® S13551244

Residential Freehold (Detached)

$499999.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Great Price Adjustment! Tour this property before its gone! WOW! That's the first impression you'll have when you step inside this beautifully main
25 Photos
Last Updated : 24 Days ago
486 Laclie Street, Simcoe, ON , MLS #S13542112 , Image - 1

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Unit-109, 486 Laclie Street Orillia, Simcoe, ON MLS® S13542112

Residential Condo & Other (Condo Apartment)

$450000.0
price drop iconPrice drop by 2.2%
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Rarely offered main floor corner condo, an exceptional opportunity at 486 Laclie Street Unit 109 in Orillia's desirable north end. This spacious two b
28 Photos
Last Updated : 24 Days ago
580 West Street S, Simcoe, ON , MLS #S13549080 , Image - 1

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Unit-Lot 209, 580 West Street S Orillia, Simcoe, ON MLS® S13549080

Residential Freehold (MobileTrailer)

$189900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to easy, carefree living in the Lakeside Estates community! This Charming 2-bedroom mobile home offers a warm and inviting atmosphere. The Din
23 Photos
Last Updated : 26 Days ago
356 West Street N, Simcoe, ON , MLS #S13577842 , Image - 1

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356 West Street N Orillia, Simcoe, ON MLS® S13577842

Residential Freehold (Detached)

$474900.0
  • 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-time buyers,
35 Photos
Last Updated : 28 Days ago
308 Hilda Street, Simcoe, ON , MLS #S13418298 , Image - 1

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308 Hilda Street Orillia, Simcoe, ON MLS® S13418298

Residential Freehold (Semi-Detached )

$399000.0
price drop iconPrice drop by 5.5%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable opportunity in Orillia! This 2-storey semi-detached home offers over 1,000 sq ft above grade with 3 bedrooms and 1 full bath, making it a g
17 Photos
Last Updated : 29 Days ago
12 Lankin Boulevard, Simcoe, ON , MLS #S13231682 , Image - 1

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Unit-40, 12 Lankin Boulevard Orillia, Simcoe, ON MLS® S13231682

Residential Condo & Other (Condo Townhouse)

$399900.0
price drop iconPrice drop by 4.3%
  • 3 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Welcome to Ontario's Sunshine City, where waterfront living, recreation, and convenience come together in one of Central Ontario's most desirable comm
4 Photos
Last Updated : 29 Days ago
221 Matchedash Street S, Simcoe, ON , MLS #S13560270 , Image - 1
221 Matchedash Street S Orillia, Simcoe, ON MLS® S13560270

Residential Freehold (Vacant Land)

$285000.0
  • < 700 sq-ft
Attention builders and investors! Partial VTB available for qualified purchaser! Vacant land for sale, corner lot on a quiet street. Building permit i
8 Photos
Last Updated : 30 Days ago
600 West Street S, Simcoe, ON , MLS #S13561268 , Image - 1

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

Residential Freehold (Detached)

$399000.0
  • 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
31 Photos
Last Updated : 32 Days ago
371 Millard Street, Simcoe, ON , MLS #S13545060 , Image - 1

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371 Millard Street Orillia, Simcoe, ON MLS® S13545060

Residential Freehold (Att/Row/Townhouse)

$499900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome home to a freehold townhouse with no monthly fees - a rare find at this price point. Inside, the layout feels warm, functional, and designed t
17 Photos
Last Updated : 37 Days ago
72 Dunedin Street, Simcoe, ON , MLS #S13518498 , Image - 1

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72 Dunedin Street Orillia, Simcoe, ON MLS® S13518498

Residential Freehold (Duplex)

$439000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Well-maintained nonconforming duplex offering two bright, spacious 1-bedroom apartments in good condition. Both units feature some updated windows, li
26 Photos
Last Updated : 48 Days ago
107 Bond Street, Simcoe, ON , MLS #S13491718 , Image - 1

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Unit-304, 107 Bond Street Orillia, Simcoe, ON MLS® S13491718

Residential Condo & Other (Condo Apartment)

$350000.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
This well-maintained 2-bedroom, 2-bathroom condo offers excellent value for investors, first-time home buyers, and downsizers alike. The bright and in
1 Photos
Last Updated : 49 Days ago
61 Front Street S, Simcoe, ON
61 Front Street S Orillia, Simcoe, ON MLS® S12921296

Residential Freehold (Vacant Land)

$199000.0
price drop iconPrice drop by 43.1%
Welcome to 61 Front Street in the heart of Orillia-where charm, convenience, and opportunity come together. Ideally located just steps from the vibran
12 Photos
Last Updated : 54 Days ago
211 Westmount Drive S, Simcoe, ON , MLS #S13223862 , Image - 1

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211 Westmount Drive S Orillia, Simcoe, ON MLS® S13223862

Residential Freehold (Detached)

$429900.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Affordable Renovation Opportunity in a Convenient West Ward Location!Bring your vision and unlock the potential of this 3+1 bedroom, 2-bathroom home s
6 Photos
Last Updated : 56 Days ago
243 Mckinnell Street, Simcoe, ON , MLS #S13460914 , Image - 1

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243 Mckinnell Street Orillia, Simcoe, ON MLS® S13460914

Residential Freehold (Detached)

$499000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Good starter or downsizing home with great potential. This bungalow is situated on a nice-sized lot. Two bedrooms on the main floor. (Current tenant u
14 Photos
Last Updated : 57 Days ago
58 Scott Street, Simcoe, ON , MLS #S13164872 , Image - 1

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58 Scott Street Orillia, Simcoe, ON MLS® S13164872

Residential Freehold (Vacant Land)

$199000.0
Opportunity to invest in Orillia's sought-after East Ward. Close to public transit, rec centre, restaurants, shopping, and 2 blocks away from all the
3 Photos
Last Updated : 58 Days ago
256 Harvey Street, Simcoe, ON , MLS #S13446928 , Image - 1
256 Harvey Street Orillia, Simcoe, ON MLS® S13446928

Residential Freehold (Vacant Land)

$285000.0
Great development opportunity in Orillia's desirable West Ward. This vacant residential lot is ideally located on a public transit route and close to
8 Photos
Last Updated : 61 Days ago
50 DUNEDIN Street, Simcoe, ON , MLS #S13440270 , Image - 1

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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
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