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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: September 26, 2026

22 Photos

323 William Street, Simcoe, ON , MLS #S13691574 , Image - 1

323 William Street Midland, Simcoe, ON MLS® S13691574

Residential Freehold (Detached)

$389000.0

Price drop by 8.0%

2 Beds
1 Baths
700-1100 sq-ft

Charming Midland Bungalow with Great Potential! Welcome to 323 William Street, a well cared for 2 bedroom, 1 bathroom bungalow situated on a generous

4 Photos

242 Barnett Avenue, Simcoe, ON , MLS #S13799500 , Image - 1

242 Barnett Avenue Midland, Simcoe, ON MLS® S13799500

Residential Freehold (Detached)

$494000.0

Price drop by 3.1%

4 Beds
2 Baths
1100-1500 sq-ft

Exceptional opportunity in Midland! Situated on an expensive double lot with impressive 97.44' frontage by 123.50' depth, this 2-storey home offers in

24 Photos

179 Seventh Street, Simcoe, ON , MLS #S13824824 , Image - 1

179 Seventh Street Midland, Simcoe, ON MLS® S13824824

Residential Freehold (Detached)

$369900.0

3 Beds
1 Baths
700-1100 sq-ft

Enjoy quiet mornings on the welcoming front porch or relaxing evenings on the private rear deck. With three bedrooms and 1 bath this century home is i

29 Photos

778 William Street, Simcoe, ON , MLS #S13764872 , Image - 1

Unit-85, 778 William Street Midland, Simcoe, ON MLS® S13764872

Residential Condo & Other (Condo Townhouse)

$399900.0

3 Beds
2 Baths
1000-1199 sq-ft

Welcome to this beautifully updated 3-bedroom, 2-bathroom condo townhouse in Midland-an excellent opportunity for families, first-time buyers, or anyo

Open House : Sat Sep 26, 10:30 AM to 12:00 PM

12 Photos

98 Fourth Street, Simcoe, ON , MLS #S13768056 , Image - 1

98 Fourth Street Midland, Simcoe, ON MLS® S13768056

Residential Freehold (Duplex)

$349900.0

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

Looking for a winter project? This property presents a great opportunity for Investors, Builders, Flippers & Handymen! This property is priced to sel

28 Photos

137 Fourth Street, Simcoe, ON , MLS #S13809860 , Image - 1

137 Fourth Street Midland, Simcoe, ON MLS® S13809860

Residential Freehold (Detached)

$349900.0

3 Beds
2 Baths
1500-2000 sq-ft

Set on an impressive 200-foot-deep lot, the property provides plenty of outdoor space to enjoy and tons of potential, along with parking for up to fiv

33 Photos

11 Ryan's Road, Simcoe, ON , MLS #S13760944 , Image - 1

11 Ryan's Road Midland, Simcoe, ON MLS® S13760944

Residential Freehold (MobileTrailer)

$225000.0

Price drop by 10.0%

2 Beds
1 Baths
700-1100 sq-ft

Looking to Downsize! Welcome to 11 Ryan's Road in Smith's Camp, Midland, a mobile home community located near beautiful Little Lake and offering plent

Open House : Sat Sep 26, 09:30 AM to 11:00 AM

11 Photos

981 wright Drive, Simcoe, ON , MLS #S13693238 , Image - 1

981 wright Drive Midland, Simcoe, ON MLS® S13693238

Residential Freehold (Att/Row/Townhouse)

$479900.0

Price drop by 3.8%

2 Beds
2 Baths
1100-1500 sq-ft

Freshly built end unit freehold bungalow townhouse, with spacious open concept living, includes good quality counter tops and good quality finishes th

Open House : Sat Sep 26, 12:00 PM to 02:00 PM

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

25 Photos

24 Lakeshore Road, Simcoe, ON , MLS #S13242028 , Image - 1

24 Lakeshore Road Midland, Simcoe, ON MLS® S13242028

Residential Freehold (MobileTrailer)

$249777.0

2 +0 Beds
1 Baths
< 700 sq-ft

Welcome to 24 Lakeshore Road in Midland, where you can enjoy beautiful waterfront sunsets and a relaxed lifestyle in a welcoming year-round community.

7 Photos

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

361 Fitton Street Midland, Simcoe, ON MLS® S13573576

Residential Freehold (Detached)

$269900.0

Price drop by 16.9%

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

Open House : Sat Sep 26, 12:00 PM to 01:00 PM

27 Photos

976 Yonge Street, Simcoe, ON , MLS #S13714356 , Image - 1

976 Yonge Street Midland, Simcoe, ON MLS® S13714356

Residential Freehold (Detached)

$485000.0

Price drop by 7.6%

1 Beds
1 Baths
700-1100 sq-ft

Charming Midland Home with Extensive Updates & Exceptional Garage - Welcome to 976 Yonge St, a well-maintained 1-bedroom, 1-bathroom home offering com

25 Photos

525 Midland Point Road, Simcoe, ON , MLS #S13739738 , Image - 1

Unit-28, 525 Midland Point Road Midland, Simcoe, ON MLS® S13739738

Residential Freehold (MobileTrailer)

$199777.0

2 +0 Beds
1 Baths
700-1100 sq-ft

Welcome to 525 Midland Point Road, Unit #28 in Leeshore Estates, a great opportunity to enjoy comfortable living in a sought-after community located i

22 Photos

314 Bay Street, Simcoe, ON , MLS #S13746464 , Image - 1

314 Bay Street Midland, Simcoe, ON MLS® S13746464

Residential Freehold (Detached)

$415000.0

Price drop by 3.5%

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

29 Photos

639 Dominion Avenue, Simcoe, ON , MLS #S13814788 , Image - 1

639 Dominion Avenue Midland, Simcoe, ON MLS® S13814788

Residential Freehold (Detached)

$424900.0

3 Beds
1 Baths
1100-1500 sq-ft

Timeless charm meets effortless in-town living on coveted Dominion Avenue. This beautifully maintained century home is a rare blend of character, comf

37 Photos

320 Scott Street, Simcoe, ON , MLS #S13772898 , Image - 1

320 Scott Street Midland, Simcoe, ON MLS® S13772898

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

Open House : Sat Sep 26, 10:00 AM to 11:30 AM

31 Photos

390 Mildred Street, Simcoe, ON , MLS #S13811184 , Image - 1

390 Mildred Street Midland, Simcoe, ON MLS® S13811184

Residential Freehold (Detached)

$349900.0

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

Top 5 Reasons You Will Love This Home: 1) Step inside and discover a home with plenty of space to make your own, where generously sized principal room

43 Photos

140 Southwinds Crescent, Simcoe, ON , MLS #S13798318 , Image - 1

140 Southwinds Crescent Midland, Simcoe, ON MLS® S13798318

Residential Freehold (Att/Row/Townhouse)

$499900.0

3 Beds
2 Baths
1100-1500 sq-ft

Don't miss out on this 3-bedroom, 1.5 bath, well-maintained end unit with thoughtful upgrades, practical features and fully fenced landscaped yard ! M

20 Photos

405 Dominion Avenue, Simcoe, ON , MLS #S13802718 , Image - 1

405 Dominion Avenue Midland, Simcoe, ON MLS® S13802718

Residential Freehold (Detached)

$399900.0

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 on the main floor 2 bedroom apartment a

15 Photos

486 Hannah Street, Simcoe, ON , MLS #S13797614 , Image - 1

486 Hannah Street Midland, Simcoe, ON MLS® S13797614

Residential Freehold (Detached)

$499900.0

5 Beds
3 Baths
2000-2500 sq-ft

Discover this standout 3-Unit investment opportunity in a friendly Midland neighbourhood. This property features modern updates on 3 floors; ***Main F

13 Photos

722 Aberdeen Boulevard, Simcoe, ON , MLS #S13805682 , Image - 1

722 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13805682

Residential Freehold (Vacant Land)

$315000.0

Top 5 Reasons You Will Love This Property: 1) Stop browsing and start building your custom luxury masterpiece, this prime 60'x131' lot offers an incre

35 Photos

696 KING Street, Simcoe, ON , MLS #S13798506 , Image - 1

Unit-56, 696 KING Street Midland, Simcoe, ON MLS® S13798506

Residential Condo & Other (Condo Townhouse)

$399900.0

1 +0 Beds
1 Baths
800-899 sq-ft

Rare opportunity for a 1 bedroom townhouse bungalow condo with attached garage in sought after Bowling Green Estates in beautiful Midland. This all br

30 Photos

277 Gloucester Street, Simcoe, ON , MLS #S13799550 , Image - 1

277 Gloucester Street Midland, Simcoe, ON MLS® S13799550

Residential Freehold (Detached)

$419000.0

3 Beds
2 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Enjoy the beauty of Georgian Bay from this beautifully updated 2-storey home, featuring a vinyl siding exter

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

27 Photos

1 Smiths Lane, Simcoe, ON , MLS #S13735984 , Image - 1

1 Smiths Lane Midland, Simcoe, ON MLS® S13735984

Residential Freehold (MobileTrailer)

$299999.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 1 Smiths Lane in Smiths Camp. You have found an affordable home providing space and accessibility in a waterfront community. This spaciou

9 Photos

798 Coral Springs Lane, Simcoe, ON , MLS #S13790194 , Image - 1

798 Coral Springs Lane Midland, Simcoe, ON MLS® S13790194

Residential Freehold (Att/Row/Townhouse)

$475000.0

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

Turn-key brick townhome in a family-friendly Midland neighbourhood, offering the space, comfort, and convenience first-time buyers have been waiting f

30 Photos

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

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

Residential Freehold (Duplex)

$419999.0

Price drop by 16.0%

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

26 Photos

346 Bay Street, Simcoe, ON , MLS #S13783804 , Image - 1

346 Bay Street Midland, Simcoe, ON MLS® S13783804

Residential Freehold (Detached)

$499900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to this charming red-brick home, where timeless character meets modern updates. Filled with warmth and personality, this home features beautif

30 Photos

308 Russell Street, Simcoe, ON , MLS #S13785364 , Image - 1

308 Russell Street Midland, Simcoe, ON MLS® S13785364

Residential Freehold (Detached)

$369900.0

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

29 Photos

45 Northland Drive, Simcoe, ON , MLS #S13721232 , Image - 1

45 Northland Drive Midland, Simcoe, ON MLS® S13721232

Residential Freehold (MobileTrailer)

$274000.0

2 Beds
1 Baths
700-1100 sq-ft

Welcome to the wonderful community of Smiths Camp! This well-maintained 2-bedroom home offers over 950 square feet of comfortable living space and sit

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