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Houses for Sale in Orillia ON Under $5 Million - P2

Showing results 31 - 60 of 263
Last Updated: September 21, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
50 Photos
Last Updated : 2 Days ago
168 Diana Drive, Simcoe, ON , MLS #S13772808 , Image - 1
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168 Diana Drive Orillia, Simcoe, ON MLS® S13772808

Residential Freehold (Detached)

$679000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
WELCOME TO WESTRIDGE - WHERE I'LL JUST RUN OUT FOR ONE THING COULD MEAN COSTCO, HOME DEPOT, DINNER... OR ALL THREE! Built in 2018 & well maintained by
12 Photos
Last Updated : 2 Days ago
167 Laclie Street, Simcoe, ON , MLS #S13794736 , Image - 1

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167 Laclie Street Orillia, Simcoe, ON MLS® S13794736

Residential Freehold (Detached)

$369000.0
  • 1 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 167 Laclie St, Orillia - a well-located property offering flexibility, recent improvements and exciting value-add potential. Set in an esta
43 Photos
Last Updated : 2 Days ago
4 Kehoe Court, Simcoe, ON , MLS #S13795260 , Image - 1

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4 Kehoe Court Orillia, Simcoe, ON MLS® S13795260

Residential Freehold (Detached)

$649900.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Charming raised bungalow nestled on a quiet cul-de-sac in a highly sought-after Orillia neighborhood. Offering over 2,000 square feet of finished, fle
50 Photos
Last Updated : 2 Days ago
104 WOODSIDE Drive, Simcoe, ON , MLS #S13795118 , Image - 1

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104 WOODSIDE Drive Orillia, Simcoe, ON MLS® S13795118

Residential Freehold (Detached)

$699900.0
  • 3 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
**MORTGAGE HELPER Possibility *** 3 BEDROOMS + 2.5 BATHROOMS + FULLY FINISHED BASEMENT! Lower level includes full bathroom, extra rooms and a separat
35 Photos
Last Updated : 2 Days ago
25 Lankin Boulevard, Simcoe, ON , MLS #S13802712 , Image - 1

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25 Lankin Boulevard Orillia, Simcoe, ON MLS® S13802712

Residential Freehold (Detached)

$725000.0
  • 4 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Here is an opportunity that is all about location, potential and a lifestyle that is difficult to duplicate. Situated on 60 feet of frontage on the La
38 Photos
Last Updated : 3 Days ago
2981 Annalysse Drive, Simcoe, ON , MLS #S13778276 , Image - 1

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2981 Annalysse Drive Orillia, Simcoe, ON MLS® S13778276

Residential Freehold (Detached)

$659900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Truly Impressive! Well appointed, freshly painted home situated in highly desirable West Ridge Place. Extremely bright and functional, offering 1,932
36 Photos
Last Updated : 3 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)

$549000.0
  • 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
11 Photos
Last Updated : 3 Days ago
1095 MISSISSAGA Street W, Simcoe, ON , MLS #S13759054 , Image - 1

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Unit-84, 1095 MISSISSAGA Street W Orillia, Simcoe, ON MLS® S13759054

Residential Condo & Other (Condo Townhouse)

$319000.0
  • 3 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Perfect starter home, downsizer or for the money conscious buyer this end unit home offers tons of privacy with no rear neighbours, lush trees and aff
8 Photos
Last Updated : 3 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)

$349000.0
price drop iconPrice drop by 12.5%
  • 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
49 Photos
Last Updated : 3 Days ago
144 Jarvis Street, Simcoe, ON , MLS #S13798166 , Image - 1

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144 Jarvis Street Orillia, Simcoe, ON MLS® S13798166

Residential Freehold (Detached)

$589900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 144 Jarvis Street, a truly special piece of Orillia history in the sought-after North Ward, just steps from the main beach waterfront of La
27 Photos
Last Updated : 3 Days ago
381 Forest Avenue S, Simcoe, ON , MLS #S13797666 , Image - 1

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381 Forest Avenue S Orillia, Simcoe, ON MLS® S13797666

Residential Freehold (Detached)

$379900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 381 Forest Avenue, South! This bright and cozy 3-bedroom, 1-bath bungalow is located in a peaceful and friendly neighbourhood. Bright and i
41 Photos
Last Updated : 3 Days ago
24 Ashton Street, Simcoe, ON , MLS #S13721122 , Image - 1

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24 Ashton Street Orillia, Simcoe, ON MLS® S13721122

Residential Freehold (Detached)

$599900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to your dream home! This sturdy, detached brick bungalow in Orillia offers the ultimate in single-level living, perfectly blending daily conve
29 Photos
Last Updated : 3 Days ago
3 Lawson Avenue, Simcoe, ON , MLS #S13783890 , Image - 1

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3 Lawson Avenue Orillia, Simcoe, ON MLS® S13783890

Residential Freehold (Detached)

$572900.0
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Turn the key and move into this clean, beautifully maintained home. This nicely renovated 3-bedroom side split has plenty to offer. The open-concept
4 Photos
Last Updated : 3 Days ago
3151 Orion Boulevard, Simcoe, ON , MLS #S13802446 , Image - 1
3151 Orion Boulevard Orillia, Simcoe, ON MLS® S13802446

Residential Freehold (Detached)

$825900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Take advantage of NEW HST REBATES with revised pricing! The appeal of Orillia living truly comes to life in communities like Westridge Trailside. Set
32 Photos
Last Updated : 3 Days ago
424 Homewood Avenue, Simcoe, ON , MLS #S13610426 , Image - 1

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424 Homewood Avenue Orillia, Simcoe, ON MLS® S13610426

Residential Freehold (Detached)

$749900.0
price drop iconPrice drop by 3.2%
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 424 Homewood located in Orillia, this exceptional property offers a rare combination of spacious living and private outdoor space on a doub
37 Photos
Last Updated : 3 Days ago
2970 Monarch Drive, Simcoe, ON , MLS #S13770714 , Image - 1

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2970 Monarch Drive Orillia, Simcoe, ON MLS® S13770714

Residential Freehold (Detached)

$899900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Exquisite pond views and breathtaking sunsets from a gorgeous cul-de-sac: this modern, beautifully finished 4-bedroom home located at 2970 Monarch Dri
8 Photos
Last Updated : 3 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
45 Photos
Last Updated : 3 Days ago
60 MUSEUM Drive, Simcoe, ON , MLS #S13674656 , Image - 1

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Unit-505, 60 MUSEUM Drive Orillia, Simcoe, ON MLS® S13674656

Residential Condo & Other (Condo Townhouse)

$750000.0
  • 2 Beds
  • 3 Baths
  • 1800-1999 sq-ft
Here is your opportunity to own an immaculate bungaloft end-unit condominium in the sought-after Leacock Village, where comfort, style, and an excepti
34 Photos
Last Updated : 3 Days ago
40 Museum Drive, Simcoe, ON , MLS #S13654160 , Image - 1

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Unit-403, 40 Museum Drive Orillia, Simcoe, ON MLS® S13654160

Residential Condo & Other (Condo Townhouse)

$614999.0
  • 2 Beds
  • 2 Baths
  • 1600-1799 sq-ft
Nestled in the heart of the scenic Leacock Village Community, this beautifully cared-for 2 bedroom 2 bathroom condo townhome offers a rare combination
50 Photos
Last Updated : 3 Days ago
4 Karen Crescent, Simcoe, ON , MLS #S13752718 , Image - 1

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4 Karen Crescent Orillia, Simcoe, ON MLS® S13752718

Residential Freehold (Detached)

$699999.0
price drop iconPrice drop by 3.4%
  • 4 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Spacious Family Home with an In-Law Suite. Over 3,000 sq. ft. of finished living space! This beautifully maintained 4-bedroom home offers generous roo
35 Photos
Last Updated : 4 Days ago
88 Pearl Drive, Simcoe, ON , MLS #S13768630 , Image - 1

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88 Pearl Drive Orillia, Simcoe, ON MLS® S13768630

Residential Freehold (Detached)

$658900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this well-maintained, first-owner home in the desirable Westridge community! Offering approximately 1,730 sq. ft. of living space, this spa
14 Photos
Last Updated : 4 Days ago
8 Edna Street, Simcoe, ON , MLS #S13670930 , Image - 1

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8 Edna Street Orillia, Simcoe, ON MLS® S13670930

Residential Freehold (Detached)

$559900.0
price drop iconPrice drop by 13.8%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to this 3-bedroom, 2-bathroom bungalow offering 1,517 sq ft above grade in a convenient location close to highway access, shopping, schools, p
21 Photos
Last Updated : 4 Days ago
800 West Ridge Boulevard, Simcoe, ON , MLS #S13798050 , Image - 1

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Unit-125, 800 West Ridge Boulevard Orillia, Simcoe, ON MLS® S13798050

Residential Freehold (Att/Row/Townhouse)

$419999.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to this beautifully 3-bedroom, 3-bathroom end-unit townhome, offering a bright, spacious, and inviting layout. Featuring an open-concept desig
50 Photos
Last Updated : 4 Days ago
390 Arthur Street, Simcoe, ON , MLS #S13546356 , Image - 1

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390 Arthur Street Orillia, Simcoe, ON MLS® S13546356

Residential Freehold (Detached)

$625000.0
price drop iconPrice drop by 3.7%
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Completely renovated from the studs in, this beautifully updated Orillia home offers modern style, flexible living space, and an unbeatable central lo
40 Photos
Last Updated : 4 Days ago
275 Gill Street, Simcoe, ON , MLS #S13797376 , Image - 1

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275 Gill Street Orillia, Simcoe, ON MLS® S13797376

Residential Freehold (Duplex)

$674900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Incredible flexibility awaits with two self-contained dwellings in one property, each with their own furnace
47 Photos
Last Updated : 4 Days ago
16 Frontier Avenue, Simcoe, ON , MLS #S13710710 , Image - 1

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16 Frontier Avenue Orillia, Simcoe, ON MLS® S13710710

Residential Freehold (Detached)

$889000.0
price drop iconPrice drop by 3.4%
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
2 storey, 6 bedroom home. Great finishings, brick and aluminum sided. Many quality features, new upgraded custom kitchen, features with center island.
33 Photos
Last Updated : 4 Days ago
111 Lucy Lane, Simcoe, ON , MLS #S13762200 , Image - 1

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111 Lucy Lane Orillia, Simcoe, ON MLS® S13762200

Residential Freehold (Att/Row/Townhouse)

$649900.0
  • 2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Well maintained and upgraded Bungalow townhome in the sought after north end of Orillia. Set back from the road providing room to park up to 4 guest v
23 Photos
Last Updated : 4 Days ago
17 Hughes Road E, Simcoe, ON , MLS #S13752344 , Image - 1

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17 Hughes Road E Orillia, Simcoe, ON MLS® S13752344

Residential Freehold (Detached)

$599900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Set on a quiet street in a fantastic North ward neighbourhood, this well-cared-for home sits on a beautiful mature lot surrounded by towering trees an
41 Photos
Last Updated : 4 Days ago
2997 Stone Ridge Boulevard, Simcoe, ON , MLS #S13559916 , Image - 1

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2997 Stone Ridge Boulevard Orillia, Simcoe, ON MLS® S13559916

Residential Freehold (Detached)

$799999.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Whether you're searching for a spacious single-family home, a true multigenerational property with a private in-law suite, or an investment opportunit
34 Photos
Last Updated : 5 Days ago
10 Andrea Crescent, Simcoe, ON , MLS #S13787772 , Image - 1

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10 Andrea Crescent Orillia, Simcoe, ON MLS® S13787772

Residential Freehold (Detached)

$649900.0
  • 3 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 10 Andrea Crescent, a beautifully maintained home that perfectly blends comfort, style, and functionality, all complemented by charming cur
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