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

Showing results 31 - 60 of 61
Last Updated: November 12, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
36 Photos
Last Updated : 17 Days ago
40 Victoria Crescent, Simcoe, ON , MLS #S14081332 , Image - 1
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Unit-24, 40 Victoria Crescent Orillia, Simcoe, ON MLS® S14081332

Residential Condo & Other (Condo Townhouse)

$349500.0
  • 3 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Lakeside living, everyday convenience and exceptional potential! Welcome to 24-40 Victoria Crescent in Orillia, where opportunity awaits just steps fr
16 Photos
Last Updated : 17 Days ago
00110 James Street E, Simcoe, ON , MLS #S14115674 , Image - 1

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00110 James Street E Orillia, Simcoe, ON MLS® S14115674

Residential Freehold (Vacant Land)

$179000.0
This vacant residential lot in Orillia's south end is a great opportunity to build your own home. Situated on James Street East in an established nei
3 Photos
Last Updated : 21 Days ago
256 Harvey Street, Simcoe, ON , MLS #S14087348 , Image - 1
256 Harvey Street Orillia, Simcoe, ON MLS® S14087348

Residential Freehold (Vacant Land)

$249900.0
price drop iconPrice drop by 12.3%
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 : 26 Days ago
600 West Street S, Simcoe, ON , MLS #S14083370 , Image - 1

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600 West Street S Orillia, Simcoe, ON MLS® S14083370

Residential Freehold (Detached)

$279899.0
price drop iconPrice drop by 19.8%
  • 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
12 Photos
Last Updated : 27 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
28 Photos
Last Updated : 27 Days ago
246 Gill Street, Simcoe, ON , MLS #S13854364 , Image - 1

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246 Gill Street Orillia, Simcoe, ON MLS® S13854364

Residential Freehold (Detached)

$375000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Attention first-time home buyers, retirees, growing families, and savvy contractors! This charming, freehold 3-bedroom home located at 246 Gill St. in
36 Photos
Last Updated : 27 Days ago
364 Arthur Street, Simcoe, ON , MLS #S13772556 , Image - 1

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364 Arthur Street Orillia, Simcoe, ON MLS® S13772556

Residential Freehold (Detached)

$499900.0
price drop iconPrice drop by 8.9%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Don't Miss This Extensively Updated & Renovated Bungalow In Orillia's West Ward. Absolutely Perfect For First-Time Homebuyers, Investors Or Those Loo
4 Photos
Last Updated : 28 Days ago
339 Gill Street, Simcoe, ON , MLS #S14081404 , Image - 1
339 Gill Street Orillia, Simcoe, ON MLS® S14081404

Residential Freehold (Detached)

$449990.0
  • < 700 sq-ft
Attention Builders, Developers And Investors! Excellent Residential Redevelopment Opportunity At 339 Gill Street In Orillia! Situated On A Corner Lot
32 Photos
Last Updated : 29 Days ago
173 Barrie Road, Simcoe, ON , MLS #S13886574 , Image - 1

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173 Barrie Road Orillia, Simcoe, ON MLS® S13886574

Residential Freehold (Detached)

$379900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 173 Barrie Road in Orillia. This vacant, move-in ready 2-storey home sits on a 50-foot lot in Orillia's West Ward and is a great option for
1 Photos
Last Updated : 30 Days ago
217 Atherley Road, Simcoe, ON
217 Atherley Road Orillia, Simcoe, ON MLS® S13819366

Residential Freehold (Vacant Land)

$279999.0
price drop iconPrice drop by 6.7%
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
38 Photos
Last Updated : 34 Days ago
441 Barrie Road, Simcoe, ON , MLS #S13710244 , Image - 1

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

Residential Condo & Other (Condo Townhouse)

$348800.0
price drop iconPrice drop by 5.7%
  • 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
12 Photos
Last Updated : 35 Days ago
43 FITTONS Road W, Simcoe, ON , MLS #S13661072 , Image - 1

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

Residential Freehold (Detached)

$479000.0
price drop iconPrice drop by 4.2%
  • 4 +0 Beds
  • 2 Baths
  • 2000-2500 sq-ft
An exciting opportunity at 43 Fittons Road West in Orillia, offering plenty of potential for homeowners, renovators and investors alike! Full of chara
19 Photos
Last Updated : 36 Days ago
331 Linwood Avenue, Simcoe, ON , MLS #S13780420 , Image - 1

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331 Linwood Avenue Orillia, Simcoe, ON MLS® S13780420

Residential Freehold (Detached)

$475000.0
price drop iconPrice drop by 5.0%
  • 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
32 Photos
Last Updated : 36 Days ago
109 Elgin Street, Simcoe, ON , MLS #S13864522 , Image - 1

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109 Elgin Street Orillia, Simcoe, ON MLS® S13864522

Residential Freehold (Detached)

$499900.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Zoned C4i, this charming two-storey brick home offers exceptional flexibility for residential, commercial, rental income, or mixed-use possibilities.
11 Photos
Last Updated : 37 Days ago
580 West Street S, Simcoe, ON , MLS #S13869374 , Image - 1

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Unit-25, 580 West Street S Orillia, Simcoe, ON MLS® S13869374

Residential Freehold (MobileTrailer)

$289500.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to easy, low-maintenance living in Lakeside Estates. This extensively updated 2-bedroom, 2-bath manufactured home combines a bright, move-in-r
7 Photos
Last Updated : 38 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
23 Photos
Last Updated : 38 Days ago
382 West Street N, Simcoe, ON , MLS #S13860604 , Image - 1

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382 West Street N Orillia, Simcoe, ON MLS® S13860604

Residential Freehold (Detached)

$325000.0
  • 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
13 Photos
Last Updated : 41 Days ago
292 MILLARD Street, Simcoe, ON , MLS #S13857866 , Image - 1

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292 MILLARD Street Orillia, Simcoe, ON MLS® S13857866

Residential Freehold (Detached)

$499900.0
  • 3 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Attention first-time homebuyers and investors! This raised bungalow in Orillia's desirable South Ward sits on an oversized 43 x 175 ft lot and offers
26 Photos
Last Updated : 41 Days ago
107 Bond Street, Simcoe, ON , MLS #S13857708 , Image - 1

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Unit-304, 107 Bond Street Orillia, Simcoe, ON MLS® S13857708

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 brightand inv
46 Photos
Last Updated : 44 Days ago
25 Simcoe Street, Simcoe, ON , MLS #S13684472 , Image - 1

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25 Simcoe Street Orillia, Simcoe, ON MLS® S13684472

Residential Freehold (Detached)

$485000.0
price drop iconPrice drop by 3.0%
  • 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
6 Photos
Last Updated : 46 Days ago
103 Mississaga Street W, Simcoe, ON , MLS #S13832824 , Image - 1

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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,
40 Photos
Last Updated : 52 Days ago
345 LINWOOD Avenue, Simcoe, ON , MLS #S13810206 , Image - 1

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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
8 Photos
Last Updated : 55 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
50 Photos
Last Updated : 57 Days ago
8 Dunn Avenue, Simcoe, ON , MLS #S13791572 , Image - 1

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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
35 Photos
Last Updated : 59 Days ago
87 Bond Street, Simcoe, ON , MLS #S13672502 , Image - 1

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87 Bond Street Orillia, Simcoe, ON MLS® S13672502

Residential Freehold (Detached)

$499000.0
price drop iconPrice 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
19 Photos
Last Updated : 63 Days ago
10 First Street, Simcoe, ON , MLS #S13736770 , Image - 1

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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
5 Photos
Last Updated : 71 Days ago
117 Colborne Street E, Simcoe, ON , MLS #S13737780 , Image - 1
117 Colborne Street E Orillia, Simcoe, ON MLS® S13737780

Residential Freehold (Vacant Land)

$260000.0
Exceptional opportunity to secure a vacant parcel in the heart of Orillia. Located at 117 Colborne Street E, this property offers an exciting opportun
2 Photos
Last Updated : 97 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
4 Photos
Last Updated : 121 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
14 Photos
Last Updated : 149 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
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