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Detached Houses for Sale in Simcoe Under $500K

Showing results 1 - 25 of 25

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: March 22, 2026

50 Photos

9 Pennsylvania Avenue, Simcoe, ON , MLS #S12240745 , Image - 1

9 Pennsylvania Avenue Wasaga Beach, Simcoe, ON MLS® S12240745

Residential Freehold (Detached)

$489000.0

Price drop by 11.1%

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 9 Pennsylvania Ave. Located in Park Place, a gated 55+ Land Lease Community, with lots to offer, including a rec plex, indoor pool, games r

48 Photos

3965 Hilltop Road, Simcoe, ON , MLS #S12899362 , Image - 1

3965 Hilltop Road Rural Ramara, Ramara, Simcoe, ON MLS® S12899362

Residential Freehold (Detached)

$498000.0

3 Beds
1 Baths
700-1100 sq-ft

Affordable Lake Simcoe Living! Welcome to 3965 Hilltop Rd in the beautiful community of Ramara, just walking minutes from the shores of Lake Simcoe. T

32 Photos

85 Theme Park Drive, Simcoe, ON , MLS #S12898318 , Image - 1

Unit-154, 85 Theme Park Drive Wasaga Beach, Simcoe, ON MLS® S12898318

Residential Freehold (Detached)

$95000.0

2 Beds
1 Baths
< 700 sq-ft

Beautifully maintained and priced to sell. Sellers are extremely motivated due to relocation. Experience the perfect seasonal retreat at the popular C

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

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

18 Photos

7682 Oak Point Road, Simcoe, ON , MLS #S12882914 , Image - 1

7682 Oak Point Road Rural Ramara, Ramara, Simcoe, ON MLS® S12882914

Residential Freehold (Detached)

$439000.0

700-1100 sq-ft

Experience spectacular LAKE COUCHICHING SUNSETS from this picturesque waterfront property on the Trent-Severn Waterway. This property presents a Uniq

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) Comfortable and spacious, this charming home offers over 1,600 square feet of above-grade living space, prov

26 Photos

7 Nipagon Circle, Simcoe, ON , MLS #S12873500 , Image - 1

7 Nipagon Circle Wasaga Beach, Simcoe, ON MLS® S12873500

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

36 Photos

12 Schooner Lane, Simcoe, ON , MLS #S12873372 , Image - 1

12 Schooner Lane Rural Tay, Tay, Simcoe, ON MLS® S12873372

Residential Freehold (Detached)

$499999.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to 12 Schooner Lane, a stunning property in a prime location in Tay! This modern smart home is perfect for those seeking year-round accommodat

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

*** Visit the REALTOR website for further information about this Listing *** Year-round home or cottage in a natural setting, near Sawlog Point in Tin

19 Photos

10 Grew Crescent, Simcoe, ON , MLS #S12797200 , Image - 1

10 Grew Crescent Penetanguishene, Simcoe, ON MLS® S12797200

Residential Freehold (Detached)

$489900.0

2 Beds
2 Baths
1500-2000 sq-ft

WALK TO THE WATER, ENJOY ONE-LEVEL LIVING & MAKE TIME FOR WHAT MATTERS MOST! Live the lifestyle you've earned in this beautifully maintained, low-main

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

50 Photos

48 Madawaska Trail, Simcoe, ON , MLS #S12845620 , Image - 1

48 Madawaska Trail Wasaga Beach, Simcoe, ON MLS® S12845620

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

16 Photos

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

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

Residential Freehold (Detached)

$321000.0

Price drop by 8.3%

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 (

44 Photos

330 Third Street, Simcoe, ON , MLS #S12846692 , Image - 1

330 Third Street Midland, Simcoe, ON MLS® S12846692

Residential Freehold (Detached)

$499000.0

2 Beds
1 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

20 Photos

439 Sundial Drive, Simcoe, ON , MLS #S12491190 , Image - 1

439 Sundial Drive Orillia, Simcoe, ON MLS® S12491190

Residential Freehold (Detached)

$499999.0

Price drop by 4.8%

3 Beds
1 Baths
700-1100 sq-ft

Situated on a generous 0.49-acre lot (approximately 60' x 330'), this raised bungalow offers a perfect blend of space and location. The home features

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

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

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

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

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

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

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

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

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

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