233+ Detached Houses for Sale in Simcoe Under $500K

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1981 Tiny Beaches Road S, Simcoe, ON , MLS #S13236488 , Image - 1

1981 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13236488

Residential Freehold (Detached)

$369900.0

Price drop by 7.5%

3 Beds
1 Baths
< 700 sq-ft

SPOTLESS AND WELL MAINTAINED 3 SEASON COTTAGE IN TINY BEACHES, SHORT DISTANCE TO WOODLAND BEACH AND EASY ACCESS TO CONVENIENCE STORE AND SHORT DISTAN

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9 EARLDOM Boulevard, Simcoe, ON , MLS #S13498684 , Image - 1

9 EARLDOM Boulevard Port McNicoll, Tay, Simcoe, ON MLS® S13498684

Residential Freehold (Detached)

$399900.0

Price drop by 3.6%

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

Steps from Grandview Beach! This charming 3-season cottage offers a wonderful opportunity to enjoy relaxed summer living just a short stroll from the

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32 Lorne Avenue, Simcoe, ON , MLS #S13544582 , Image - 1

32 Lorne Avenue Collingwood, Simcoe, ON MLS® S13544582

Residential Freehold (Detached)

$499000.0

3 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Rare opportunity to secure an oversized approximately 66'x132' lot in the heart of Collingwood, where you ca

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537 O'leary Lane, Simcoe, ON , MLS #S13588406 , Image - 1

537 O'leary Lane Victoria Harbour, Tay, Simcoe, ON MLS® S13588406

Residential Freehold (Detached)

$495000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to this charming bungalow in the quiet waterfront community of Victoria Harbour, where relaxed living and Georgian Bay views cometogether. Thi

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1053 Elm Road, Simcoe, ON , MLS #N13490276 , Image - 1

1053 Elm Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13490276

Residential Freehold (Detached)

$465000.0

2 Beds
1 Baths
700-1100 sq-ft

Attention First-Time Buyers, Cottage Seekers & Investors!? Dreaming of getting out of the city and owning an affordable, move-in-ready home near the w

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173 Barrie Road, Simcoe, ON , MLS #S13486552 , Image - 1

173 Barrie Road Orillia, Simcoe, ON MLS® S13486552

Residential Freehold (Detached)

$399000.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to 173 Barrie Road, a wonderful 2 storey detached house on 50ft lot perfect for first-timebuyers or investors, located in the heart of Orillia

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5 Myiinggan Miikaans Lane, Simcoe, ON , MLS #S13521302 , Image - 1

5 Myiinggan Miikaans Lane Beausoleil First Nation, Christian Island 30, Simcoe, ON MLS® S13521302

Residential Freehold (Detached)

$399000.0

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

Enjoy an amazing island family cottage just steps from a Caribbean-like sandy beach in the sunshine overlooking the clear blue waters of Georgian Bay!

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20 Marilyn Avenue N, Simcoe, ON , MLS #S13489146 , Image - 1

20 Marilyn Avenue N Wasaga Beach, Simcoe, ON MLS® S13489146

Residential Freehold (Detached)

$399000.0

Price drop by 11.1%

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

This cottage has been owned by the same family since 2005 .There are two water and two sewer connections. This cottage sits on a large triangular

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45 ALBERT Street N, Simcoe, ON , MLS #S13551244 , Image - 1

45 ALBERT Street N Orillia, Simcoe, ON MLS® S13551244

Residential Freehold (Detached)

$499999.0

3 Beds
2 Baths
1100-1500 sq-ft

Great Price Adjustment! Tour this property before its gone! WOW! That's the first impression you'll have when you step inside this beautifully main

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5 Robert Street, Simcoe, ON , MLS #S13583486 , Image - 1

5 Robert Street 400 North, Barrie, Simcoe, ON MLS® S13583486

Residential Freehold (Detached)

$499900.0

2 Beds
1 Baths
700-1100 sq-ft

Top Reasons You'll Love this Home: Affordable and move-in ready, just a short walk or drive to Barrie's waterfront, downtown, Allandale Waterfront GO

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8 Belle Isle Arm N/A, Simcoe, ON , MLS #N13164136 , Image - 1

8 Belle Isle Arm N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N13164136

Residential Freehold (Detached)

$314900.0

Price drop by 7.4%

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to this lovingly maintained and updated 2 bedroom home located in the desirable adult community of Sandy Cove acres. The new buyers may have t

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30 Illinois Crescent, Simcoe, ON , MLS #S13558966 , Image - 1

30 Illinois Crescent Wasaga Beach, Simcoe, ON MLS® S13558966

Residential Freehold (Detached)

$479000.0

2 +0 Beds
2 Baths
1500-2000 sq-ft

Welcome to 30 Illinois Crescent, nestled in the heart of Park Place Estates. Wasaga Beach's premier 55+ gated community, where comfort, connection, an

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6 Gander Cove N/A, Simcoe, ON , MLS #N13479862 , Image - 1

6 Gander Cove N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N13479862

Residential Freehold (Detached)

$339000.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 6 Gander Cove, nestled in the vibrant adult lifestyle community of Sandy Cove Acres in Innisfil! This beautifully maintained bungalow is si

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5594 Upper Big Chute Road, Simcoe, ON , MLS #S13580386 , Image - 1

5594 Upper Big Chute Road Rural Severn, Severn, Simcoe, ON MLS® S13580386

Residential Freehold (Detached)

$469900.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 5594 Upper Big Chute Rd, a move-in ready, 1,020 sq. ft. home offering seamless, one-level living with zero stairs. This peaceful 2-bed, 1-b

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36 Sanford Street, Simcoe, ON , MLS #S13579022 , Image - 1

36 Sanford Street Sanford, Barrie, Simcoe, ON MLS® S13579022

Residential Freehold (Detached)

$499900.0

3 Beds
1 Baths
700-1100 sq-ft

BARRIE BUNGALOW! Welcome to this charming move-in ready 3-bedroom, 1-bath bungalow in a desirable Barrie neighbourhood. Bright and inviting, this wel

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356 West Street N, Simcoe, ON , MLS #S13577842 , Image - 1

356 West Street N Orillia, Simcoe, ON MLS® S13577842

Residential Freehold (Detached)

$474900.0

4 Beds
1 Baths
1100-1500 sq-ft

Welcome to 356 West St N in Orillia's desirable North Ward. This affordable four-bedroom home offers plenty of space for families, first-time buyers,

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117 Fox Street, Simcoe, ON , MLS #S13577448 , Image - 1

117 Fox Street Penetanguishene, Simcoe, ON MLS® S13577448

Residential Freehold (Detached)

$323000.0

4 Beds
1 Baths
1500-2000 sq-ft

Prime Investment in Penetanguishene Attention investors and flippers! This solid 4-bedroom home sits on an impressive 0.54-acre lot (89 ft x 264 ft),

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28 Harriet Street, Simcoe, ON , MLS #S13576262 , Image - 1

28 Harriet Street Penetanguishene, Simcoe, ON MLS® S13576262

Residential Freehold (Detached)

$399900.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to this charming 3-bedroom bungalow nestled on a generous 49' x 165' lot in the heart of Penetanguishene. This home is an excellent opportunit

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183 Paradise Avenue, Simcoe, ON , MLS #S13127128 , Image - 1

183 Paradise Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13127128

Residential Freehold (Detached)

$379000.0

Price drop by 5.2%

3 Beds
1 Baths
< 700 sq-ft

Welcome to 183 Paradise Avenue, this 3-bedroom, 1-bath home located in the heart of beautiful Port McNicoll. Just minutes from the waterfront, this pr

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224 Tiny Beaches Road S Road, Simcoe, ON , MLS #S13568156 , Image - 1

224 Tiny Beaches Road S Road Rural Tiny, Tiny, Simcoe, ON MLS® S13568156

Residential Freehold (Detached)

$424900.0

1 Beds
1 Baths
< 700 sq-ft

Imagine waking up just steps from the soft sands of Georgian Bay, coffee in hand, with the sound of the waves calling you to the beach. Welcome to you

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915 Vindin Street, Simcoe, ON , MLS #S13561308 , Image - 1

915 Vindin Street Midland, Simcoe, ON MLS® S13561308

Residential Freehold (Detached)

$499900.0

3 Beds
2 Baths
1100-1500 sq-ft

Offered for the first time by its original owners, this 3 bedroom, 2 bathroom raised bungalow sits on just over half an acre, surrounded by mature tre

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8 Arbor Road, Simcoe, ON , MLS #S13565114 , Image - 1

8 Arbor Road Rural Tiny, Tiny, Simcoe, ON MLS® S13565114

Residential Freehold (Detached)

$489900.0

2 Beds
1 Baths
< 700 sq-ft

YEAR-ROUND, FULLY WINTERIZED HOME/COTTAGE JUST STEPS TO THE BEACH! Located in the highly sought-after Balm Beach, this charming property offers the pe

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7682 Oak Point Road, Simcoe, ON , MLS #S13547300 , Image - 1

7682 Oak Point Road Rural Ramara, Ramara, Simcoe, ON MLS® S13547300

Residential Freehold (Detached)

$349000.0

700-1100 sq-ft

YES YOU CAN OWN WATERFRONT! Spectacular LAKE COUCHICHING SUNSETS from this picturesque waterfront property on the Trent-Severn Waterway. A Unique OPP

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314 Bay Street, Simcoe, ON , MLS #S13438566 , Image - 1

314 Bay Street Midland, Simcoe, ON MLS® S13438566

Residential Freehold (Detached)

$439900.0

Price drop by 4.3%

2 Beds
1 Baths
700-1100 sq-ft

A wonderful opportunity for first-time buyers or downsizers, this charming detached 2-bedroom home is move-in ready. From the moment you arrive, the i

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48 Madawaska Trail, Simcoe, ON , MLS #S13150930 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S13150930

Residential Freehold (Detached)

$405900.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to your new home in Wasaga! This land lease home is the perfect option for 4-season living without the high purchase price. We're located in t

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26 Dundee Drive, Simcoe, ON , MLS #S13561972 , Image - 1

26 Dundee Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13561972

Residential Freehold (Detached)

$395000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to this solid all-brick raised bungalow with attached garage, ideally located in a highly sought-after neighbourhood just a short walk to the

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101 Tecumseth Pines Drive, Simcoe, ON , MLS #N13561798 , Image - 1

101 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13561798

Residential Freehold (Detached)

$469900.0

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

Enjoy the carefree-living adult lifestyle that awaits you at Tecumseth Pines just minutes from Tottenham, where residents can enjoy a range of ameniti

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600 West Street S, Simcoe, ON , MLS #S13561268 , Image - 1

600 West Street S Orillia, Simcoe, ON MLS® S13561268

Residential Freehold (Detached)

$399000.0

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

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103 Madawaska Trail, Simcoe, ON , MLS #S13561226 , Image - 1

103 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S13561226

Residential Freehold (Detached)

$128000.0

2 Beds
1 Baths
700-1100 sq-ft

TURN KEY : EVERYTHING INCLUDED:PARK FEES PAID 2026 Welcome to 103 Madawaska Trail. Discover the perfect seasonal retreat in one Wasaga Beach's most so

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16 ZOO PARK Road, Simcoe, ON , MLS #S13559356 , Image - 1

16 ZOO PARK Road Wasaga Beach, Simcoe, ON MLS® S13559356

Residential Freehold (Detached)

$399900.0

2 +0 Beds
1 Baths
< 700 sq-ft

A SWEET WASAGA BEACH COTTAGE WITH DEEDED WATER ACCESS. Tucked just steps from the shoreline and overlooking hints of the bay and marina, this charming

Detached Houses for Sale in Simcoe Under $500K - P5

Rosehaven Simcoe Woods