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Houses for Sale in Midland ON Under $500K

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Are you looking for houses under $500k for sale in Midland ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Midland. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Midland. Whether you’re looking to buy houses under under $500k in Midland ON for residential living or as investment opportunities, our listings allow you to filter by amenities, property age, number of bedrooms and much more. Explore a diverse range of Midland houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: August 12, 2026

20 Photos

405 Dominion Avenue, Simcoe, ON , MLS #S13506512 , Image - 1

405 Dominion Avenue Midland, Simcoe, ON MLS® S13506512

Residential Freehold (Detached)

$439900.0

Price drop by 4.3%

4 Beds
2 Baths
1500-2000 sq-ft

Solid century home with 2 separate apartments with separate entrances on separate water and hydro meters. Live in the main floor 2 bedroom apartment a

31 Photos

8 Lakeshore Road, Simcoe, ON , MLS #S13103884 , Image - 1

8 Lakeshore Road Midland, Simcoe, ON MLS® S13103884

Residential Freehold (MobileTrailer)

$199900.0

Price drop by 20.0%

1 Beds
1 Baths
< 700 sq-ft

Enjoy easy, affordable waterfront living on beautiful Little Lake in Midland. Set on a spacious double lot in Smith's Camp, this mobile home offers a

29 Photos

281 Elizabeth Street, Simcoe, ON , MLS #S13661090 , Image - 1

281 Elizabeth Street Midland, Simcoe, ON MLS® S13661090

Residential Freehold (Detached)

$479777.0

2 Beds
2 Baths
700-1100 sq-ft

Beautifully renovated and move-in ready, this charming 2-bedroom home is a wonderful opportunity in a desirable Midland neighbourhood. Thoughtfully up

3 Photos

38 Northland Road, Simcoe, ON , MLS #S13659410 , Image - 1

38 Northland Road Midland, Simcoe, ON MLS® S13659410

Residential Freehold (MobileTrailer)

$225000.0

2 Beds
1 Baths
700-1100 sq-ft

Affordable Lakeside Living! Welcome to this well maintained 2 bedroom, 1 bath mobile home offering an affordable opportunity in Midland's desirable Sm

20 Photos

1053 Glen Bogie Crescent, Simcoe, ON , MLS #S13597252 , Image - 1

1053 Glen Bogie Crescent Midland, Simcoe, ON MLS® S13597252

Residential Freehold (Detached)

$499900.0

3 Beds
1 Baths
700-1100 sq-ft

Welcome to Midland's most sought-after west end neighbourhood, where mature trees, quiet streets, and long-time residents create a true sense of commu

29 Photos

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

37 Photos

320 Scott Street, Simcoe, ON , MLS #S13538324 , Image - 1

320 Scott Street Midland, Simcoe, ON MLS® S13538324

Residential Freehold (Detached)

$495000.0

3 Beds
1 Baths
700-1100 sq-ft

This well-kept 3-bedroom, 1-bathroom all-brick backsplit offers a great family-friendly layout in a central Midland location. The main level features

44 Photos

330 Third Street, Simcoe, ON , MLS #S13044912 , Image - 1

330 Third Street Midland, Simcoe, ON MLS® S13044912

Residential Freehold (Detached)

$439000.0

Price drop by 8.4%

2 Beds
2 Baths
700-1100 sq-ft

Timeless Charm & Modern Comfort in the Heart of Midland! Welcome to a home that instantly feels just right. This beautifully updated 2-storey century

12 Photos

816 Jane Boulevard, Simcoe, ON , MLS #S13607774 , Image - 1

816 Jane Boulevard Midland, Simcoe, ON MLS® S13607774

Residential Condo & Other (Condo Townhouse)

$475000.0

2 Beds
2 Baths
1000-1199 sq-ft

THOUGHTFULLY UPDATED BUNGALOW STEPS FROM LITTLE LAKE! What if homeownership came with more freedom? Ditch the lawnmower and snow shovel for this beaut

30 Photos

525 Midland Point Road, Simcoe, ON , MLS #S13575430 , Image - 1

Unit-3, 525 Midland Point Road Midland, Simcoe, ON MLS® S13575430

Residential Freehold (MobileTrailer)

$279000.0

1 Beds
1 Baths
700-1100 sq-ft

Welcome To Carefree Waterfront Living In The Desirable Lee Shore Estates, A Well-Maintained 55+ Community. This Charming 1-Bedroom, 1-Bathroom Home Of

7 Photos

361 Fitton Street, Simcoe, ON , MLS #S13573576 , Image - 1

361 Fitton Street Midland, Simcoe, ON MLS® S13573576

Residential Freehold (Detached)

$309900.0

Price drop by 4.6%

2 Beds
1 Baths
700-1100 sq-ft

Ideal for first-time buyers, investors, or those looking to downsize, this home offers a functional layout with plenty of potential. Natural light fil

21 Photos

255 Yonge Street, Simcoe, ON , MLS #S13647444 , Image - 1

255 Yonge Street Midland, Simcoe, ON MLS® S13647444

Residential Freehold (Detached)

$449000.0

2 Beds
1 Baths
700-1100 sq-ft

Whether you're searching for the perfect starter home, looking to downsize, or seeking a great investment opportunity, this charming bungalow is sure

22 Photos

30 Berts Road, Simcoe, ON , MLS #S13041068 , Image - 1

30 Berts Road Midland, Simcoe, ON MLS® S13041068

Residential Freehold (MobileTrailer)

$249900.0

Price drop by 12.3%

2 Beds
1 Baths
700-1100 sq-ft

Experience the charm of this mobile home in the heart of Smiths Park. This inviting residence offers 2 bedrooms, 1 bathroom, and a flexible den, all s

33 Photos

1339 Everton Road, Simcoe, ON , MLS #S13625138 , Image - 1

1339 Everton Road Midland, Simcoe, ON MLS® S13625138

Residential Freehold (Semi-Detached )

$489900.0

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

Welcome to this bright, cozy and private 3 bedroom, 2 bath move in ready semi-detached bungalow on a large lot in the sought after Sunnyside neighborh

37 Photos

469 Robert Street, Simcoe, ON , MLS #S13630326 , Image - 1

469 Robert Street Midland, Simcoe, ON MLS® S13630326

Residential Freehold (Detached)

$220000.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to your next great opportunity in central Midland! Whether you're looking to restore the existing structure or start anew, the possibilities a

30 Photos

642-644 Bay Street, Simcoe, ON , MLS #S13532098 , Image - 1

642-644 Bay Street Midland, Simcoe, ON MLS® S13532098

Residential Freehold (Duplex)

$444900.0

Price drop by 11.0%

5 Beds
3 Baths
2000-2500 sq-ft

Attention Investors or First Time Home Buyers. Amazing Opportunity. Side by Side Duplex. Live in One Side and Rent Out the Other One. Or Rent Out Both

21 Photos

19 Vics Road, Simcoe, ON , MLS #S13013734 , Image - 1

19 Vics Road Midland, Simcoe, ON MLS® S13013734

Residential Freehold (MobileTrailer)

$299900.0

2 Beds
1 Baths
1100-1500 sq-ft

Welcome to simple, low-maintenance living. Situated on one of the largest lots in the park, this beautifully updated double-wide offers space, privacy

50 Photos

256 Manly Street, Simcoe, ON , MLS #S13456666 , Image - 1

256 Manly Street Midland, Simcoe, ON MLS® S13456666

Residential Freehold (Detached)

$349900.0

Price drop by 5.4%

3 Beds
2 Baths
1500-2000 sq-ft

Century home opportunity in the heart of Midland! This character-filled 3 bedroom home offers a 4-piece bathroom plus an additional 1-piece bath, spac

37 Photos

369 Queen Street, Simcoe, ON , MLS #S13560212 , Image - 1

369 Queen Street Midland, Simcoe, ON MLS® S13560212

Residential Freehold (Detached)

$349900.0

2 +1 Beds
2 Baths
1100-1500 sq-ft

This one is personal. This was my grandma's house-the place I grew up visiting for homemade apple pies, her home cooking and more family memories than

8 Photos

418 Dominion Avenue, Simcoe, ON , MLS #S13445334 , Image - 1

418 Dominion Avenue Midland, Simcoe, ON MLS® S13445334

Residential Freehold (Detached)

$499990.0

Price drop by 15.3%

7 +1 Beds
3 Baths
2500-3000 sq-ft

Rare opportunity to own a spacious Victorian-style home in the heart of Midland with views of beautiful Georgian Bay. Offering approximately 3,000 sq.

9 Photos

354 Midland Avenue, Simcoe, ON , MLS #S13436614 , Image - 1

354 Midland Avenue Midland, Simcoe, ON MLS® S13436614

Residential Freehold (Detached)

$399990.0

Price drop by 16.7%

5 Beds
2 Baths
1500-2000 sq-ft

Perfect investment live in and run your business from this property, many of the commercial elements done, perfect for any type of office, Insurance,

40 Photos

680 Ontario Street, Simcoe, ON , MLS #S13602160 , Image - 1

680 Ontario Street Midland, Simcoe, ON MLS® S13602160

Residential Freehold (Detached)

$474900.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to the heart of Midland! Situated on an impressive lot 104 ft x 50 ft (double lot frontage), this beautifully updated home offers exceptional

30 Photos

308 Russell Street, Simcoe, ON , MLS #S13601082 , Image - 1

308 Russell Street Midland, Simcoe, ON MLS® S13601082

Residential Freehold (Detached)

$389900.0

3 Beds
1 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Bright, custom-designed kitchen thoughtfully crafted for both style and functionality, with an abundance of

28 Photos

379 Gloucester Street, Simcoe, ON , MLS #S13542010 , Image - 1

379 Gloucester Street Midland, Simcoe, ON MLS® S13542010

Residential Freehold (Detached)

$299777.0

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

Welcome to 379 Gloucester Street in Midland, a fantastic opportunity for first-time buyers, investors, or anyone looking for a rewarding renovation pr

27 Photos

1 Smiths Lane, Simcoe, ON , MLS #S13531568 , Image - 1

1 Smiths Lane Midland, Simcoe, ON MLS® S13531568

Residential Freehold (MobileTrailer)

$349000.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 1 Smiths Lane Road. Looking for an affordable home with more space for less? This spacious 2-bedroom, 1.5 bath home is located in Smith's C

17 Photos

808 Jane Boulevard, Simcoe, ON , MLS #S13596314 , Image - 1

808 Jane Boulevard Midland, Simcoe, ON MLS® S13596314

Residential Condo & Other (Condo Townhouse)

$429900.0

2 +0 Beds
2 Baths
1200-1399 sq-ft

This affordable property is priced to sell and ready to make your own. Don't judge a book by its cover! You will be pleasantly surprized by the size o

14 Photos

857 Birchwood Drive, Simcoe, ON , MLS #S13537548 , Image - 1

857 Birchwood Drive Midland, Simcoe, ON MLS® S13537548

Residential Freehold (Detached)

$449000.0

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

SUN-FILLED BUNGALOW LIVING JUST MINUTES FROM MIDLAND'S WATERFRONT! Escape to a peaceful, tree-lined neighbourhood where quiet streets, mature trees, a

21 Photos

3 Northland Road, Simcoe, ON , MLS #S13492936 , Image - 1

3 Northland Road Midland, Simcoe, ON MLS® S13492936

Residential Freehold (MobileTrailer)

$253900.0

2 Beds
1 Baths
700-1100 sq-ft

Affordable Living with Great Amenities! Looking for an affordable home with extras you don't usually get at this price? This charming 2-bedroom, 1-bat

18 Photos

204 Gianetto Drive, Simcoe, ON , MLS #S12628254 , Image - 1

204 Gianetto Drive Midland, Simcoe, ON MLS® S12628254

Residential Freehold (Vacant Land)

$199000.0

Build your Dream Home! Breath taking views of Midland Harbour! This generously sized 0.7 acre building lot offers a rare opportunity in one of Midland

9 Photos

317 Hugel Avenue, Simcoe, ON , MLS #S12890206 , Image - 1

317 Hugel Avenue Midland, Simcoe, ON MLS® S12890206

Residential Freehold (Duplex)

$450000.0

Price drop by 2.2%

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

Legal duplex located within walking distance to downtown Midland. Excellent investment opportunity with positive cash flow and reliable tenants in pla

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