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

Showing results 31 - 60 of 62
Last Updated: September 27, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
14 Photos
Last Updated : 19 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.
26 Photos
Last Updated : 20 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
23 Photos
Last Updated : 23 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
39 Photos
Last Updated : 23 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
25 Photos
Last Updated : 24 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 : 24 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
5 Photos
Last Updated : 25 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
43 Photos
Last Updated : 26 Days ago
12 LANKIN Boulevard, Simcoe, ON , MLS #S13730198 , Image - 1

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Unit-31, 12 LANKIN Boulevard Orillia, Simcoe, ON MLS® S13730198

Residential Condo & Other (Condo Townhouse)

$405000.0
  • 3 +0 Beds
  • 1 Baths
  • 1200-1399 sq-ft
Discover the perfect blend of comfort, value, and lakeside living in this charming 3-bedroom townhome at the revitalized Lankin Shores community, just
48 Photos
Last Updated : 27 Days ago
174 Barrie Road, Simcoe, ON , MLS #S13099924 , Image - 1

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174 Barrie Road Orillia, Simcoe, ON MLS® S13099924

Residential Freehold (Duplex)

$478900.0
price drop iconPrice drop by 7.7%
  • 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
41 Photos
Last Updated : 30 Days ago
1047 Mississaga Street W, Simcoe, ON , MLS #S13631396 , Image - 1

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Unit-307, 1047 Mississaga Street W Orillia, Simcoe, ON MLS® S13631396

Residential Condo & Other (Condo Apartment)

$329000.0
  • 2 Beds
  • 1 Baths
  • 800-899 sq-ft
Simple Living Starts Here. Whether you're purchasing your first home, downsizing into a more manageable space, or simply looking for a low-maintenance
41 Photos
Last Updated : 31 Days ago
137 Dufferin Street, Simcoe, ON , MLS #S13654852 , Image - 1

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137 Dufferin Street Orillia, Simcoe, ON MLS® S13654852

Residential Freehold (Detached)

$274900.0
price drop iconPrice drop by 3.5%
  • 1 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
WOW! Check out this updated price! OPEN HOUSE Saturday, August 29th 1-3pm. Seller is motivated! Seller says, bring any reasonable Offer. Ideal
22 Photos
Last Updated : 32 Days ago
246 Mary Street, Simcoe, ON , MLS #S13652024 , Image - 1

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246 Mary Street Orillia, Simcoe, ON MLS® S13652024

Residential Freehold (Detached)

$499900.0
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
VERSATILE 2-STOREY HOME WITH TWO SELF-CONTAINED LIVING SPACES ON AN EXTRA-DEEP LOT IN THE HEART OF ORILLIA! Rarely offered and full of opportunity, th
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
3 Photos
Last Updated : 39 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
17 Photos
Last Updated : 39 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)

$419000.0
price drop iconPrice drop by 4.6%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Well-maintained nonconforming 2-unit dwelling offering two bright, spacious 1-bedroom apartments in good condition. Both units feature some updated wi
1 Photos
Last Updated : 45 Days ago
61 Front Street S, Simcoe, ON
61 Front Street S Orillia, Simcoe, ON MLS® S12921296

Residential Freehold (Vacant Land)

$129000.0
price drop iconPrice drop by 63.1%
Welcome to 61 Front Street in the heart of Orillia-where charm, convenience, and opportunity come together. Ideally located just steps from the vibran
23 Photos
Last Updated : 48 Days ago
492 Laclie Street, Simcoe, ON , MLS #S13504794 , Image - 1

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Unit-204, 492 Laclie Street Orillia, Simcoe, ON MLS® S13504794

Residential Condo & Other (Condo Apartment)

$325000.0
  • 2 Beds
  • 1 Baths
  • 900-999 sq-ft
Just minutes away you'll find the sparkling waterfront at Couchiching Beach Park, scenic walking and cycling trails, marinas, and golf at the nearby C
13 Photos
Last Updated : 50 Days ago
292 MILLARD Street, Simcoe, ON , MLS #S13209562 , Image - 1

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292 MILLARD Street Orillia, Simcoe, ON MLS® S13209562

Residential Freehold (Detached)

$499900.0
price drop iconPrice drop by 8.4%
  • 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
2 Photos
Last Updated : 51 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 : 52 Days ago
0 James Street, Simcoe, ON , MLS #S13100600 , Image - 1
0 James Street Orillia, Simcoe, ON MLS® S13100600

Residential Freehold (Vacant Land)

$218000.0
Exceptional opportunity to own a vacant residential lot in Orillia's east end. Located on James St E, this property offers excellent potential within
21 Photos
Last Updated : 55 Days ago
107 Bond Street, Simcoe, ON , MLS #S13215402 , Image - 1

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Unit-202, 107 Bond Street Orillia, Simcoe, ON MLS® S13215402

Residential Condo & Other (Condo Apartment)

$342000.0
price drop iconPrice drop by 2.0%
  • 2 Beds
  • 1 Baths
  • 900-999 sq-ft
Welcome to this bright and beautifully updated 2-bedroom, 1-bath end-unit condo that truly feels like home. With its open-concept layout, natural ligh
34 Photos
Last Updated : 56 Days ago
1095 Mississaga Street W, Simcoe, ON , MLS #S13222416 , Image - 1

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Unit-121, 1095 Mississaga Street W Orillia, Simcoe, ON MLS® S13222416

Residential Condo & Other (Condo Townhouse)

$425000.0
  • 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
15 Photos
Last Updated : 58 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 : 58 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 : 59 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
25 Photos
Last Updated : 69 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
4 Photos
Last Updated : 75 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
26 Photos
Last Updated : 94 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
14 Photos
Last Updated : 103 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
4 Photos
Last Updated : 109 Days ago
339 Gill Street, Simcoe, ON , MLS #S13185992 , Image - 1
339 Gill Street Orillia, Simcoe, ON MLS® S13185992

Residential Freehold (Detached)

$499990.0
  • < 700 sq-ft
Welcome To 339 Gill Street! This Corner Property Is One Of A Kind! Suitable For Many Uses Including An Apartment Building Or A Townhouse Project. R2 Z
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