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Houses for Sale in Orillia ON Under $5 Million - P4

Showing results 91 - 120 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)
17 Photos
Last Updated : 7 Days ago
107 Bond Street, Simcoe, ON , MLS #S13512384 , Image - 1
Image With Blur overlay

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Unit-208, 107 Bond Street Orillia, Simcoe, ON MLS® S13512384

Residential Condo & Other (Condo Apartment)

$319900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Bright and freshly painted 2-bedroom, 1-bathroom condo in Orillia, located on the second floor.This well-designed unit features a functional layout, h
45 Photos
Last Updated : 7 Days ago
93 North Street W, Simcoe, ON , MLS #S13779350 , Image - 1

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93 North Street W Orillia, Simcoe, ON MLS® S13779350

Residential Freehold (Detached)

$569900.0
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Opportunity meets versatility in Orillia's highly sought-after North Ward. This legal duplex presents an exceptional investment opportunity while offe
46 Photos
Last Updated : 7 Days ago
28 Borland Street W, Simcoe, ON , MLS #S13779316 , Image - 1

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28 Borland Street W Orillia, Simcoe, ON MLS® S13779316

Residential Freehold (Detached)

$639900.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Located in the North Ward of Orillia this brick bungalow sits on a fully fenced lot. Close to schools, downtown, shopping and transit. This charming
30 Photos
Last Updated : 7 Days ago
255 DIANA Drive, Simcoe, ON , MLS #S13752398 , Image - 1

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255 DIANA Drive Orillia, Simcoe, ON MLS® S13752398

Residential Freehold (Detached)

$699000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
This is an exquisite open-concept family home nestled in the charming community of Orillia! This impressive residence boasts 2,373 square feet of luxu
24 Photos
Last Updated : 7 Days ago
40 Michelle Drive, Simcoe, ON , MLS #S13770422 , Image - 1

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40 Michelle Drive Orillia, Simcoe, ON MLS® S13770422

Residential Freehold (Att/Row/Townhouse)

$539900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
The RIGHT MOVE starts here! If you've been waiting for an affordable 3-bedroom home that doesn't come with monthly condo fees, this updated freehold t
44 Photos
Last Updated : 7 Days ago
331 Moffat Street, Simcoe, ON , MLS #S13778702 , Image - 1

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331 Moffat Street Orillia, Simcoe, ON MLS® S13778702

Residential Freehold (Detached)

$565000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
A charming 1 1/2 storey, move-in ready 3 bedroom home in Orillia. A short distance to the beach, downtown, and shopping. This home is located on a lar
33 Photos
Last Updated : 8 Days ago
90 Orchard Point, Simcoe, ON , MLS #S13623946 , Image - 1

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Unit-311, 90 Orchard Point Orillia, Simcoe, ON MLS® S13623946

Residential Condo & Other (Condo Apartment)

$699000.0
  • 1 +1 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Experience the best of lakeside living in this beautifully appointed 1-bedroom plus den, 2-bathroom condo offering breathtaking, unobstructed views of
43 Photos
Last Updated : 8 Days ago
3112 Emperor Drive, Simcoe, ON , MLS #S13778062 , Image - 1

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3112 Emperor Drive Orillia, Simcoe, ON MLS® S13778062

Residential Freehold (Detached)

$739000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
NEW PRICE & MOTIVATED SELLER! Exceptional value in Orillia's highly desirable West Ridge community. This very well maintained 3 bedroom, 3 bathroom de
19 Photos
Last Updated : 8 Days ago
43 Olive Crescent, Simcoe, ON , MLS #S13771326 , Image - 1

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Unit-103, 43 Olive Crescent Orillia, Simcoe, ON MLS® S13771326

Residential Condo & Other (Condo Apartment)

$599900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
EXPERIENCE LAKESIDE LUXURY AT PARADISE COVE!!!
28 Photos
Last Updated : 8 Days ago
93 Westmount Drive S, Simcoe, ON , MLS #S13464512 , Image - 1

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93 Westmount Drive S Orillia, Simcoe, ON MLS® S13464512

Residential Freehold (Detached)

$749900.0
price drop iconPrice drop by 5.0%
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Fantastic investment opportunity at 93 Westmount Drive S in Orillia! This versatile two-unit income property sits on a huge lot and offers ample parki
50 Photos
Last Updated : 9 Days ago
315 Oxford Street, Simcoe, ON , MLS #S13714740 , Image - 1

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315 Oxford Street Orillia, Simcoe, ON MLS® S13714740

Residential Freehold (Duplex)

$675000.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 315 Oxford Street, a turnkey legal duplex offering an excellent combination of income potential, functionality, parking, and outdoor living
27 Photos
Last Updated : 9 Days ago
354 Atherley Road, Simcoe, ON , MLS #S13776522 , Image - 1

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Unit-211, 354 Atherley Road Orillia, Simcoe, ON MLS® S13776522

Residential Condo & Other (Condo Apartment)

$579900.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
Lake Couchiching Condo Living With Resort-Style Amenities, Underground Parking & Locker! Experience effortless lakefront living at Panoramic Point, wh
32 Photos
Last Updated : 9 Days ago
453 Mooney Crescent, Simcoe, ON , MLS #S13751904 , Image - 1

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453 Mooney Crescent Orillia, Simcoe, ON MLS® S13751904

Residential Freehold (Detached)

$739800.0
  • 3 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Tucked away near the end of a quiet dead-end street and just steps from the canal, this bright and welcoming home is located in one of Orillia's most
46 Photos
Last Updated : 10 Days ago
27 Brandon Crescent, Simcoe, ON , MLS #S13774908 , Image - 1

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27 Brandon Crescent Orillia, Simcoe, ON MLS® S13774908

Residential Freehold (Detached)

$839900.0
  • 5 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 27 Brandon Crescent - a beautifully renovated 2-storey family home tucked into a friendly, established Orillia neighbourhood. Offering 5 be
23 Photos
Last Updated : 10 Days ago
102 West Street N, Simcoe, ON , MLS #S13771100 , Image - 1

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102 West Street N Orillia, Simcoe, ON MLS® S13771100

Residential Freehold (Detached)

$624900.0
price drop iconPrice drop by 0.0%
  • 5 +1 Beds
  • 4 Baths
  • 1100-1500 sq-ft
A rare opportunity to own a legal, income-producing triplex in the heart of Orillia. Set on a generous lot with ample surface parking, this property o
4 Photos
Last Updated : 10 Days ago
Lot 44 Orion Boulevard, Simcoe, ON , MLS #S13773858 , Image - 1
Lot 44 Orion Boulevard Orillia, Simcoe, ON MLS® S13773858

Residential Freehold (Detached)

$796900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
PRICE REFLECTS HST REBATE. Construction has started. Introducing the Carmel Model (Elevation A) in the highly sought-after West Ridge community on Ori
21 Photos
Last Updated : 10 Days ago
486 Laclie Street, Simcoe, ON , MLS #S13772916 , Image - 1

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Unit-Unit 111, 486 Laclie Street Orillia, Simcoe, ON MLS® S13772916

Residential Condo & Other (Condo Apartment)

$439900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to Maple Arbour Condominiums, one of Orillia's most sought-after communities. This bright and spacious ground-floor unit offers convenient, lo
23 Photos
Last Updated : 10 Days ago
345 East Street, Simcoe, ON , MLS #S13696788 , Image - 1

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345 East Street Orillia, Simcoe, ON MLS® S13696788

Residential Freehold (Detached)

$424000.0
price drop iconPrice drop by 3.4%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
A detached home in an established Orillia neighbourhood, offered under $450,000. A rare entry point into the market at this price, with room to add yo
1 Photos
Last Updated : 10 Days ago
69 Olive Crescent, Simcoe, ON
69 Olive Crescent Orillia, Simcoe, ON MLS® S13461502

Residential Freehold (Detached)

$845999.0
price drop iconPrice drop by 6.0%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to your dream lakeside escape on the sparkling shores of Lake Simcoe, where comfort, style, and breathtaking southern lake views come together
47 Photos
Last Updated : 10 Days ago
377 MARY Street, Simcoe, ON , MLS #S13770980 , Image - 1

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377 MARY Street Orillia, Simcoe, ON MLS® S13770980

Residential Freehold (Detached)

$699900.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to this beautifully maintained two story home that's ready for its next family. Offering 4 spacious bedrooms and 3.5 bathrooms, as well as mai
44 Photos
Last Updated : 10 Days ago
10 Wyn Wood Lane, Simcoe, ON , MLS #S13770604 , Image - 1

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10 Wyn Wood Lane Orillia, Simcoe, ON MLS® S13770604

Residential Freehold (Att/Row/Townhouse)

$699999.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
10 Wyn Wood Lane - A luxury townhome nestled in an exclusive lakeside community. Steps from the lake, this exceptional residence offers over 2000 sq.f
19 Photos
Last Updated : 11 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
32 Photos
Last Updated : 11 Days ago
89 Lightfoot Drive, Simcoe, ON , MLS #S13767480 , Image - 1

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89 Lightfoot Drive Orillia, Simcoe, ON MLS® S13767480

Residential Freehold (Other)

$1099900.0
  • 3 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to this stunning 3-storey end-unit townhome in the highly sought-after Sunshine Harbour community! Offering unobstructed views of Lake Couchic
40 Photos
Last Updated : 11 Days ago
82 Fourth Street, Simcoe, ON , MLS #S13767062 , Image - 1

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82 Fourth Street Orillia, Simcoe, ON MLS® S13767062

Residential Freehold (Detached)

$679000.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 82 Fourth Street, a charming side-split home located in Orillia's highly sought-after North Ward. This beautifully maintained residence off
32 Photos
Last Updated : 11 Days ago
2974 Monarch Drive, Simcoe, ON , MLS #S13539430 , Image - 1

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2974 Monarch Drive Orillia, Simcoe, ON MLS® S13539430

Residential Freehold (Detached)

$826900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
*PRICE REFLECTS HST REBATE* Fully built Mancini Homes, located in the highly sought after West Ridge Community on Monarch Drive. Home consists of many
50 Photos
Last Updated : 11 Days ago
26 Dalton Crescent N, Simcoe, ON , MLS #S13687630 , Image - 1

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26 Dalton Crescent N Orillia, Simcoe, ON MLS® S13687630

Residential Freehold (Detached)

$674900.0
  • 3 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to this spacious family home in Orillia's highly sought-after North Ward, situated on an impressive oversized lot adjacent to a park! Brimming
14 Photos
Last Updated : 11 Days ago
69 DIANA Drive, Simcoe, ON , MLS #S13725978 , Image - 1

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69 DIANA Drive Orillia, Simcoe, ON MLS® S13725978

Residential Freehold (Detached)

$649900.0
price drop iconPrice drop by 5.8%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to a home that effortlessly blends opportunity with everyday comfort. This charming two-storey , Four Bedroom detached residence with a 2 car
38 Photos
Last Updated : 11 Days ago
117 Isabella Drive, Simcoe, ON , MLS #S13663374 , Image - 1

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117 Isabella Drive Orillia, Simcoe, ON MLS® S13663374

Residential Freehold (Att/Row/Townhouse)

$619900.0
price drop iconPrice drop by 1.6%
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Opportunity knocks-motivated sellers and an incredible turn-key property loaded with pristine upgrades make this a Westridge home you won't want to mi
46 Photos
Last Updated : 11 Days ago
408 Mooney Crescent, Simcoe, ON , MLS #S13620122 , Image - 1

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408 Mooney Crescent Orillia, Simcoe, ON MLS® S13620122

Residential Freehold (Detached)

$999900.0
price drop iconPrice drop by 4.8%
  • 3 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Discover waterfront living in the highly sought-after Couchiching Point community! This spacious 3+1 bedroom bungalow is situated on a generous lot wi
27 Photos
Last Updated : 11 Days ago
21 Matchedash Street S, Simcoe, ON , MLS #S13764736 , Image - 1

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Unit-502, 21 Matchedash Street S Orillia, Simcoe, ON MLS® S13764736

Residential Condo & Other (Condo Apartment)

$689000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Experience modern condo living at the sought-after Matchedash Lofts, ideally positioned in the heart of his
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