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Orillia Detached Houses for Sale

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Last Updated: November 06, 2026

48 Photos

265 Diana Drive, Simcoe, ON , MLS #S14157380 , Image - 1

265 Diana Drive Orillia, Simcoe, ON MLS® S14157380

Residential Freehold (Detached)

$894900.0

4 Beds
4 Baths
2000-2500 sq-ft

One-Of-A-Kind & Move-In Ready! You Won't Want To Miss Your Opportunity To Own This Rare Offering In The Highly Sought After Community Of Westridge.

45 Photos

64 Vanessa Drive, Simcoe, ON , MLS #S13696376 , Image - 1

64 Vanessa Drive Orillia, Simcoe, ON MLS® S13696376

Residential Freehold (Detached)

$649900.0

Price drop by 8.5%

3 Beds
3 Baths
1100-1500 sq-ft

Beautifully finished and move-in ready, this 3-bedroom, 3-bathroom home is located in Orillia's popular West Ridge community. Bright and airy, it offe

34 Photos

383 High Street, Simcoe, ON , MLS #S14112002 , Image - 1

383 High Street Orillia, Simcoe, ON MLS® S14112002

Residential Freehold (Detached)

$529900.0

6 Beds
2 Baths
1100-1500 sq-ft

Raised bungalow 1152 Square feet 3+3 bedrooms. Two kitchens two bathrooms. Few updates plumbing, electrical, most fixtures are original. A seniors

32 Photos

535 High Street N, Simcoe, ON , MLS #S14155156 , Image - 1

535 High Street N Orillia, Simcoe, ON MLS® S14155156

Residential Freehold (Detached)

$639900.0

2 +1 Beds
2 Baths
700-1100 sq-ft

Where VINTAGE CHARM meets MODERN LUXURY - Welcome to 535 High Street - from the moment you arrive you will be captivated by the stunning curb appeal o

Open House : Sat Nov 14, 12:00 PM to 02:00 PM

30 Photos

12 Francis Road, Simcoe, ON , MLS #S13549548 , Image - 1

12 Francis Road Orillia, Simcoe, ON MLS® S13549548

Residential Freehold (Detached)

$1079900.0

3 Beds
2 Baths
1100-1500 sq-ft

What makes a property truly rare? A beautifully updated, move-in-ready home on an exceptional mature lot in one of Orillia's most sought-after neighbo

Open House : Sat Nov 07, 11:00 AM to 01:00 PM

20 Photos

233 West Street N, Simcoe, ON , MLS #S14133180 , Image - 1

233 West Street N Orillia, Simcoe, ON MLS® S14133180

Residential Freehold (Detached)

$549000.0

3 +2 Beds
2 Baths
700-1100 sq-ft

One Property, Endless Possibilities! Discover an exceptional opportunity in Orillia with this detached raised bungalow offering two self-contained res

32 Photos

424 Homewood Avenue, Simcoe, ON , MLS #S13610426 , Image - 1

424 Homewood Avenue Orillia, Simcoe, ON MLS® S13610426

Residential Freehold (Detached)

$649900.0

Price drop by 16.1%

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

49 Photos

10 Invermara Court, Simcoe, ON , MLS #S13846104 , Image - 1

Unit-36, 10 Invermara Court Orillia, Simcoe, ON MLS® S13846104

Residential Freehold (Detached)

$949000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to 10 - 36 Invermara Court a stunning bungaloft nestled within the exclusive gated waterfront community of Sophie's Landing on the shores of L

12 Photos

167 Laclie Street, Simcoe, ON , MLS #S13794736 , Image - 1

167 Laclie Street Orillia, Simcoe, ON MLS® S13794736

Residential Freehold (Detached)

$329900.0

Price drop by 10.6%

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

1 Photos

69 Olive Crescent Orillia, Simcoe, ON MLS® S14125460

Residential Freehold (Detached)

$800000.0

3 +0 Beds
1 Baths
700-1100 sq-ft

Updated, turnkey Lake Simcoe waterfront with municipal water, sewer and year-round access on a municipal road-no well or septic to maintain! Boat thro

30 Photos

37 Toboggan Hill Drive, Simcoe, ON , MLS #S14031846 , Image - 1

37 Toboggan Hill Drive Orillia, Simcoe, ON MLS® S14031846

Residential Freehold (Detached)

$649900.0

Price drop by 4.4%

3 +0 Beds
2 Baths
1100-1500 sq-ft

Welcome to 37 Toboggan Hill Drive, an immaculately maintained home on one of Orillia's most highly desired streets. Recent updates include a newer roo

Open House : Sun Nov 08, 12:30 PM to 02:00 PM

41 Photos

68 CINDY LEE Crescent, Simcoe, ON , MLS #S14107618 , Image - 1

68 CINDY LEE Crescent Orillia, Simcoe, ON MLS® S14107618

Residential Freehold (Detached)

$599000.0

Price drop by 2.6%

3 +2 Beds
2 Baths
700-1100 sq-ft

WELCOME TO 68 CINDY LEE CRESCENT - 5 BEDROOMS, 2 KITCHENS & IMPRESSIVE UPGRADES! Located on a quiet crescent in Orillia's established West Ward, this

Open House : Sun Nov 08, 12:30 PM to 03:00 PM

50 Photos

15 Walker Avenue, Simcoe, ON , MLS #S14144196 , Image - 1

15 Walker Avenue Orillia, Simcoe, ON MLS® S14144196

Residential Freehold (Detached)

$599000.0

3 Beds
2 Baths
1100-1500 sq-ft

Completele remodelled, 2 storey 1150 sq ft brick and aluminum above grade home with 27' x 10' carport, paved driveway, large 101.71' x 149.87' irregul

40 Photos

8 Vanessa Drive, Simcoe, ON , MLS #S14123398 , Image - 1

8 Vanessa Drive Orillia, Simcoe, ON MLS® S14123398

Residential Freehold (Detached)

$599900.0

2 Beds
1 Baths
1100-1500 sq-ft

Charming, inviting, and full of potential! Welcome to 8 Vanessa Drive in Orillia, a lovely 2-bedroom home with spaces to relax, entertain, and make yo

Open House : Sat Nov 07, 01:00 PM to 03:00 PM

46 Photos

28 Borland Street W, Simcoe, ON , MLS #S14146938 , Image - 1

28 Borland Street W Orillia, Simcoe, ON MLS® S14146938

Residential Freehold (Detached)

$599999.0

3 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 b

Open House : Sat Nov 07, 12:00 PM to 03:00 PM

50 Photos

30 Pearl Drive, Simcoe, ON , MLS #S14146438 , Image - 1

30 Pearl Drive Orillia, Simcoe, ON MLS® S14146438

Residential Freehold (Detached)

$725000.0

3 +1 Beds
3 Baths
1500-2000 sq-ft

Welcome to this beautifully maintained home on Pearl Drive. The spacious, connected living and dining area is filled with natural light from two large

Open House : Sat Nov 07, 01:00 PM to 03:00 PM

8 Photos

440 Gill Street, Simcoe, ON , MLS #S13845032 , Image - 1

440 Gill Street Orillia, Simcoe, ON MLS® S13845032

Residential Freehold (Detached)

$425000.0

4 Beds
1 Baths
1100-1500 sq-ft

Opportunity awaits. This classic brick 2-storey home is ideal for first time buyers, savvy rental investors or young families looking to move into a

24 Photos

8 Lavallee Crescent, Simcoe, ON , MLS #S13720482 , Image - 1

8 Lavallee Crescent Orillia, Simcoe, ON MLS® S13720482

Residential Freehold (Detached)

$585000.0

Price drop by 1.7%

2 +1 Beds
2 Baths
700-1100 sq-ft

Beautifully updated 3-bedroom, 2-bathroom bungalow nestled on a quiet, low-traffic crescent, just a short walk from Couchiching Beach Park, historic d

28 Photos

275 Harvey Street, Simcoe, ON , MLS #S14145494 , Image - 1

275 Harvey Street Orillia, Simcoe, ON MLS® S14145494

Residential Freehold (Detached)

$469900.0

4 Beds
1 Baths
1100-1500 sq-ft

Inviting & Thoughtfully Maintained Detached 2-Storey Family Home Nestled On Large 60 x 165Ft Lot Just Under 0.25 Acres, In Friendly Community Of Orill

41 Photos

4090 Wainman Line, Simcoe, ON , MLS #S13706262 , Image - 1

4090 Wainman Line Orillia, Simcoe, ON MLS® S13706262

Residential Freehold (Detached)

$774900.0

Price drop by 8.8%

2 +1 Beds
2 Baths
1500-2000 sq-ft

Welcome to this spacious and versatile home featuring a welcoming foyer with a large closet, convenient access to the accessory apartment, and a gener

Open House : Sat Nov 07, 11:00 AM to 12:30 PM

45 Photos

67 Vanessa Drive, Simcoe, ON , MLS #S13687440 , Image - 1

67 Vanessa Drive Orillia, Simcoe, ON MLS® S13687440

Residential Freehold (Detached)

$649900.0

Price drop by 9.7%

2 +2 Beds
2 Baths
700-1100 sq-ft

Beautifully landscaped ranch bungalow with a walkout basement, offering spacious living areas and quality finishes throughout. A high stone walkway le

Open House : Sun Nov 08, 02:30 PM to 04:00 PM

41 Photos

137 Dufferin Street, Simcoe, ON , MLS #S13654852 , Image - 1

137 Dufferin Street Orillia, Simcoe, ON MLS® S13654852

Residential Freehold (Detached)

$250000.0

Price drop by 12.3%

1 +1 Beds
2 Baths
700-1100 sq-ft

WOW! Check out this updated price! Seller is motivated! Seller says, bring any reasonable Offer. Be sure to check out the Sold prices of vacant Bu

28 Photos

148 Coldwater Road W, Simcoe, ON , MLS #S14099924 , Image - 1

148 Coldwater Road W Orillia, Simcoe, ON MLS® S14099924

Residential Freehold (Detached)

$369000.0

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to 148 Coldwater Rd W. Excellent location with amenities at your fingertips & Victoria Park down the street. Endless potential awaits inthis s

Open House : Sat Nov 14, 02:00 PM to 04:00 PM

11 Photos

3183 Orion Boulevard, Simcoe, ON , MLS #S13855950 , Image - 1

3183 Orion Boulevard Orillia, Simcoe, ON MLS® S13855950

Residential Freehold (Detached)

$989900.0

3 Beds
3 Baths
2500-3000 sq-ft

Premier Location, Premium Lot, and Luxury Finishes! Nothing cookie cutter in this brand new home built by Mariposa Homes. With unique architectural d

Open House : Sun Nov 08, 11:00 AM to 01:00 PM

15 Photos

3195 Orion Boulevard, Simcoe, ON , MLS #S13855942 , Image - 1

3195 Orion Boulevard Orillia, Simcoe, ON MLS® S13855942

Residential Freehold (Detached)

$999900.0

4 Beds
3 Baths
2000-2500 sq-ft

BRAND NEW and READY FOR OCCUPANCY! Premier location in Orillia's sought after Trailside Community close to schools, shopping, and trails. Premium land

Open House : Sun Nov 08, 11:00 AM to 01:00 PM

50 Photos

3046 Monarch Drive, Simcoe, ON , MLS #S14140308 , Image - 1

3046 Monarch Drive Orillia, Simcoe, ON MLS® S14140308

Residential Freehold (Detached)

$918000.0

4 +3 Beds
5 Baths
2500-3000 sq-ft

Welcome to this exceptional raised bungalow with a unique loft design, offering an impressive blend of luxury, functionality, and versatility. Set on

40 Photos

82 Fourth Street, Simcoe, ON , MLS #S14031416 , Image - 1

82 Fourth Street Orillia, Simcoe, ON MLS® S14031416

Residential Freehold (Detached)

$649900.0

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

21 Photos

15 Watson Court, Simcoe, ON , MLS #S14110208 , Image - 1

15 Watson Court Orillia, Simcoe, ON MLS® S14110208

Residential Freehold (Detached)

$699900.0

4 Beds
2 Baths
1100-1500 sq-ft

BANKS ARE PREDICTING HOUSE PRICES TO GO UP IN 2027. BUY NOW BEFORE THAT HAPPENS! 15 watson Court is an all Brick Family Home on a Quiet Cul-de-Sac! Si

Open House : Sun Nov 08, 12:00 PM to 02:00 PM

50 Photos

104 WOODSIDE Drive, Simcoe, ON , MLS #S13795118 , Image - 1

104 WOODSIDE Drive Orillia, Simcoe, ON MLS® S13795118

Residential Freehold (Detached)

$679900.0

Price drop by 2.9%

3 +2 Beds
4 Baths
1500-2000 sq-ft

LENDER SALE Easy to Re-Establish Operational Inlaw Apartment w Separate Entrance via Garage/Spotless/Move In ready/Freshly painted main & second floo

24 Photos

279 Nottawasaga Street, Simcoe, ON , MLS #S14119014 , Image - 1

279 Nottawasaga Street Orillia, Simcoe, ON MLS® S14119014

Residential Freehold (Detached)

$495000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 279 Nottawasaga Street in Orillia! This charming bungalow sits on an impressive 49 x 171 ft lot and features a detached garage, offering pl

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