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Detached Houses for Sale in Simcoe Under $500K

Showing results 1 - 22 of 22

Square Yards Canada can assist you in finding the ideal detached homes in Simcoe. Browse the options of several detached homes for sale Under $500K in Simcoe comprising 1 to 5 beds. The detached houses for sale Under $500K in Simcoe are listed by owners and brokers offering first-rate amenities and services in upscale neighbourhoods in Simcoe.

Last Updated: February 05, 2026

50 Photos

48 Madawaska Trail, Simcoe, ON , MLS #S12538492 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S12538492

Residential Freehold (Detached)

$419000.0

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

37 Photos

31 Desroches Trail, Simcoe, ON , MLS #S12750138 , Image - 1

31 Desroches Trail Rural Tiny, Tiny, Simcoe, ON MLS® S12750138

Residential Freehold (Detached)

$495500.0

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

Offered for the first time, this inviting year-round home or cottage embodies the relaxed, timeless lifestyle Lafontaine is known for. Nestled on a qu

32 Photos

173 Barrie Road, Simcoe, ON , MLS #S12746702 , Image - 1

173 Barrie Road Orillia, Simcoe, ON MLS® S12746702

Residential Freehold (Detached)

$399999.0

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-time buyers or investors, located in the heart of Orilli

25 Photos

81 Corner Brook Trail, Simcoe, ON , MLS #N12744692 , Image - 1

81 Corner Brook Trail Alcona, Innisfil, Simcoe, ON MLS® N12744692

Residential Freehold (Detached)

$440000.0

2 Beds
2 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Located in an Adult Lifestyle community of Sandycove Acres this home offers thoughtfully selected upgrades t

Pre-Construction

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard

From $879,990 - $1,339,990

Project Info

Units
Townhouses

Property Mix

Floorplans coming soon

Developer:Rosehaven Homes

13 Photos

250 Kingfisher Avenue, Simcoe, ON , MLS #S12654300 , Image - 1

250 Kingfisher Avenue Port McNicoll, Tay, Simcoe, ON MLS® S12654300

Residential Freehold (Detached)

$299900.0

Price drop by 14.1%

700-1100 sq-ft

You've just arrived in Paradise Point! This Seasonal cottage sits on a 60' x 146' lot in the heart of this beloved community. Potential !!! Project to

32 Photos

3 Courtland Street, Simcoe, ON , MLS #S12740528 , Image - 1

3 Courtland Street Orillia, Simcoe, ON MLS® S12740528

Residential Freehold (Detached)

$369000.0

2 Beds
1 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Zoned Village Commercial, this unique property offers endless flexibility to live comfortably, run a busines

28 Photos

147 Dufferin Street, Simcoe, ON , MLS #S12739156 , Image - 1

147 Dufferin Street Orillia, Simcoe, ON MLS® S12739156

Residential Freehold (Detached)

$359000.0

1 Beds
2 Baths
< 700 sq-ft

Welcome to this cute and cozy home located in Orillia's West Ward neighbourhood. This home has lots of natural light and plenty of potential for any f

16 Photos

685 Reid Street, Simcoe, ON , MLS #N12731388 , Image - 1

685 Reid Street Alcona, Innisfil, Simcoe, ON MLS® N12731388

Residential Freehold (Detached)

$399900.0

1 Beds
1 Baths
< 700 sq-ft

* Permits are ready to build a second floor and a garage * This beautiful bungalow is located on a peaceful, low-traffic street with the added benefit

21 Photos

349 Balm Beach Road W, Simcoe, ON , MLS #S12732976 , Image - 1

349 Balm Beach Road W Rural Tiny, Tiny, Simcoe, ON MLS® S12732976

Residential Freehold (Detached)

$499900.0

3 Beds
1 Baths
700-1100 sq-ft

Enjoy the beauty of year-round cottage living in Tiny with only a 3-minute walk to one of the most desired beaches on Georgian Bay. 3-bedroom open con

39 Photos

11 Talsi Road, Simcoe, ON , MLS #N12705946 , Image - 1

11 Talsi Road Rural Essa, Essa, Simcoe, ON MLS® N12705946

Residential Freehold (Detached)

$285000.0

3 Beds
1 Baths
700-1100 sq-ft

Welcome to 11 Talsi Rd! As seen in the CBC Gem series Something Undone, this fully furnished 3-bedroom, 1-bathroom Viceroy Cedar Cottage offers the ul

23 Photos

1 GRAY Street, Simcoe, ON , MLS #S12185393 , Image - 1

1 GRAY Street Coldwater, Severn, Simcoe, ON MLS® S12185393

Residential Freehold (Detached)

$479900.0

Price drop by 8.6%

3 Beds
1 Baths
700-1100 sq-ft

Check out this very affordable and well maintained 1,260 total finished square foot home. Three bedrooms on the main floor, attached garage, and a ful

12 Photos

26 George Avenue, Simcoe, ON , MLS #S12670070 , Image - 1

26 George Avenue Wasaga Beach, Simcoe, ON MLS® S12670070

Residential Freehold (Detached)

$449900.0

3 Beds
1 Baths
700-1100 sq-ft

Opportunity Knocks! Attention Renovators, Contractors, Investors, Builders And First Time Buyers. 3 Bedroom Bungalow Located On A Quiet Cul-De Sac. Ki

10 Photos

17 Private Drive, Simcoe, ON , MLS #N12626674 , Image - 1

17 Private Drive Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12626674

Residential Freehold (Detached)

$288000.0

< 700 sq-ft

Rare Waterfront Opportunity On The Holland River! This 50 X 100 Ft Property Is Accessed Via A Private Road With Direct Access To Yonge St Offering A P

4 Photos

2766 Ireton Street, Simcoe, ON , MLS #N12325788 , Image - 1

2766 Ireton Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N12325788

Residential Freehold (Detached)

$475000.0

3 Beds
1 Baths
700-1100 sq-ft

Incredible opportunity to build your dream home or cottage retreat on a premium lot just steps from one of Innisfil's most beautiful beaches. This exp

35 Photos

2 WHITE PINES Trail, Simcoe, ON , MLS #S12596254 , Image - 1

2 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S12596254

Residential Freehold (Detached)

$134999.0

2 Beds
1 Baths
< 700 sq-ft

Enjoy your Seasonal Getaway at Wasaga Countrylife Resort! Now is the time to secure your seasonal cottage retreat! This immaculate 2009 Northlander Co

48 Photos

36 Tecumseth Pines Drive, Simcoe, ON , MLS #N12426310 , Image - 1

36 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12426310

Residential Freehold (Detached)

$499000.0

Price drop by 1.2%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to Tecumseth Pines, where peaceful country surroundings meet an active and welcoming 55+ lifestyle! Nestled in a beautiful community just minu

36 Photos

7 60th Street S, Simcoe, ON , MLS #S12461340 , Image - 1

7 60th Street S Wasaga Beach, Simcoe, ON MLS® S12461340

Residential Freehold (Detached)

$399999.0

Price drop by 8.5%

1 Beds
1 Baths
700-1100 sq-ft

Nestled in the heart of Wasaga Beach, this property offers a unique opportunity to own a pieceof this vibrant community. This detached single-family h

16 Photos

3520 Bennett Avenue, Simcoe, ON , MLS #S12546060 , Image - 1

3520 Bennett Avenue Rural Severn, Severn, Simcoe, ON MLS® S12546060

Residential Freehold (Detached)

$350000.0

1 Baths
700-1100 sq-ft

Small Home & a Beautiful Spot. Possibly this 350k value investment could be turned into 700-800k in a few short months. This property features lots (

38 Photos

309 Manly Street, Simcoe, ON , MLS #S12509724 , Image - 1

309 Manly Street Midland, Simcoe, ON MLS® S12509724

Residential Freehold (Detached)

$424900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 309 Manly Street in Midland. Whether you are looking for an investment or just starting out this property has upside potential. Featuring

30 Photos

2135 Champlain Road, Simcoe, ON , MLS #S12232829 , Image - 1

2135 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S12232829

Residential Freehold (Detached)

$459000.0

Price drop by 17.9%

2 Beds
1 Baths
700-1100 sq-ft

For more info on this property, please click the Brochure button. Year-round home or cottage in a natural setting, near Sawlog Point in Tiny. 2 Bedro

44 Photos

330 Third Street, Simcoe, ON , MLS #S12443761 , Image - 1

330 Third Street Midland, Simcoe, ON MLS® S12443761

Residential Freehold (Detached)

$499000.0

2 Beds
2 Baths
700-1100 sq-ft

Charming Century Home in the Heart of Midland! Perfect for First-Time Buyers & Young Families! Step into this beautifully renovated and immaculately c

26 Photos

7 Nipagon Circle, Simcoe, ON , MLS #S12399590 , Image - 1

7 Nipagon Circle Wasaga Beach, Simcoe, ON MLS® S12399590

Residential Freehold (Detached)

$135900.0

2 Beds
1 Baths
< 700 sq-ft

Welcome to 7 Nipagon Cir, a remarkable 2015 Northlander cottage in the desirable Parkbridge's Country Life Gated Resort. This charming property featur

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