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Houses for Sale in Midland ON Under $5 Million

Showing results 1 - 30 of 186

Are you looking for houses under $5m 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 $5m 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 $5m, including freehold homes, condos, and commercial properties.

Last Updated: September 21, 2026

30 Photos

583 Aberdeen Boulevard, Simcoe, ON , MLS #S13717354 , Image - 1

583 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13717354

Residential Freehold (Vacant Land)

$800000.0

Welcome to 583 Aberdeen Boulevard, a prime waterfront building lot with breathtaking views of Georgian Bay and nestled among luxury waterfront homes i

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

34 Photos

615 Bay Street, Simcoe, ON , MLS #S13810826 , Image - 1

615 Bay Street Midland, Simcoe, ON MLS® S13810826

Residential Freehold (Detached)

$594900.0

3 Beds
2 Baths
1500-2000 sq-ft

Calling GTA Buyers and Buyers looking for move-in ready convience!! Here's your opportunity to escape the GTA Without Sacrificing Convenience! Imagine

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

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

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

40 Photos

359 Galloway Boulevard, Simcoe, ON , MLS #S13764804 , Image - 1

359 Galloway Boulevard Midland, Simcoe, ON MLS® S13764804

Residential Freehold (Detached)

$617300.0

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

Welcome to 359 Galloway Blvd, a beautifully maintained 3-bedroom, 2-bath bungalow where pride of ownership is evident inside and out. Bright and welco

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

26 Photos

769 Pratt Avenue, Simcoe, ON , MLS #S13619928 , Image - 1

769 Pratt Avenue Midland, Simcoe, ON MLS® S13619928

Residential Freehold (Detached)

$524900.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to 769 Pratt Avenue, a move-in-ready bungalow tucked away on a quiet cul-de-sac in Midland. This well maintained home is an excellent opportun

Open House : Sat Sep 26, 01:00 PM to 02:30 PM

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

15 Photos

9513 County Rd 93 Road NE, Simcoe, ON , MLS #S13803118 , Image - 1

9513 County Rd 93 Road NE Midland, Simcoe, ON MLS® S13803118

Residential Freehold (Detached)

$999999.0

4 Beds
2 Baths
2000-2500 sq-ft

ONE OF A KIND! THIS UNIQUE 1994 SQ FT RANCH BUNGALOW SITS ON 15.43 ACRE HIGHWAY LOT. 4 BEDROOMS, 2 4-PC BATHS, PARTIALLY FINISHED BASEMENT 400 Sq Ft W

27 Photos

48 Riverwalk Place, Simcoe, ON , MLS #S13691226 , Image - 1

48 Riverwalk Place Midland, Simcoe, ON MLS® S13691226

Residential Freehold (Detached)

$939900.0

Price drop by 6.0%

4 +2 Beds
4 Baths
2000-2500 sq-ft

Welcome to this remarkable 3+2 bedroom home in a scenic Midland setting with a 3 minute walk to Georgian Bay on a walking path directly off the back y

25 Photos

456 Parkview Court, Simcoe, ON , MLS #S13804058 , Image - 1

456 Parkview Court Midland, Simcoe, ON MLS® S13804058

Residential Freehold (Detached)

$845000.0

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

There is something special about finding a home that gives you both the space you need and the lifestyle you want. At 456 Parkview Court, you'll find

39 Photos

282 Norene Street, Simcoe, ON , MLS #S13556214 , Image - 1

282 Norene Street Midland, Simcoe, ON MLS® S13556214

Residential Freehold (Duplex)

$599900.0

Price drop by 4.0%

4 +3 Beds
3 Baths
1100-1500 sq-ft

Great value can be found in this well located West End Duplex which is vacant. Perfect opportunity for Investor to set own rents or for a Multi-Genera

50 Photos

936 Jordeli Lane, Simcoe, ON , MLS #S13719048 , Image - 1

936 Jordeli Lane Midland, Simcoe, ON MLS® S13719048

Residential Freehold (Detached)

$799900.0

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

Welcome to this extremely well cared for home located in sought after neighbourhood with seasonal views of Little Lake. This all brick home situated o

46 Photos

947 Montreal Street, Simcoe, ON , MLS #S13798268 , Image - 1

947 Montreal Street Midland, Simcoe, ON MLS® S13798268

Residential Freehold (Detached)

$565000.0

2 +0 Beds
1 Baths
1100-1500 sq-ft

Act now on this value packed all brick bungalow located in prime West end location of Midland. This well cared for home is being offered for the first

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

50 Photos

635 William Street, Simcoe, ON , MLS #S13786982 , Image - 1

635 William Street Midland, Simcoe, ON MLS® S13786982

Residential Freehold (Detached)

$764900.0

3 Beds
3 Baths
3000-3500 sq-ft

Welcome to a home where comfortable main-level living meets opportunity to create something more. The main floor of this incredible home features an u

42 Photos

179 Luckport Crescent, Simcoe, ON , MLS #S13190410 , Image - 1

179 Luckport Crescent Midland, Simcoe, ON MLS® S13190410

Residential Freehold (Detached)

$749900.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome to a home that checks all the boxes for comfortable family living in one of the areas most desierable neighbourhoods. This beautifully maintai

26 Photos

993 Whitney Crescent, Simcoe, ON , MLS #S13802666 , Image - 1

993 Whitney Crescent Midland, Simcoe, ON MLS® S13802666

Residential Freehold (Detached)

$939900.0

4 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Exquisite home situated on a premium lot in an outstanding neighbourhood 2) Extensive upgrades include all n

43 Photos

699 Aberdeen Boulevard, Simcoe, ON , MLS #S12984502 , Image - 1

Unit-905, 699 Aberdeen Boulevard Midland, Simcoe, ON MLS® S12984502

Residential Condo & Other (Condo Apartment)

$629000.0

Price drop by 3.2%

2 +0 Beds
2 Baths
1000-1199 sq-ft

Beautiful Rose model at sought after Tiffin Pier Condo. This 2 bed 2 bath waterfront condo offers 1,102 sf plus balcony and water views from every roo

22 Photos

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

323 William Street Midland, Simcoe, ON MLS® S13691574

Residential Freehold (Detached)

$423000.0

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

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

45 Photos

642 Randles Crescent, Simcoe, ON , MLS #S13501296 , Image - 1

642 Randles Crescent Midland, Simcoe, ON MLS® S13501296

Residential Freehold (Detached)

$579000.0

Price drop by 3.3%

3 Beds
2 Baths
1100-1500 sq-ft

Welcome home to this beautifully maintained raised bungalow in Midland's desirable east end! Offering 3 spacious bedrooms and 2 bathrooms, this inviti

41 Photos

404 Manly Street, Simcoe, ON , MLS #S13793438 , Image - 1

404 Manly Street Midland, Simcoe, ON MLS® S13793438

Residential Freehold (Detached)

$634900.0

4 Beds
3 Baths
2500-3000 sq-ft

RARE 3-STOREY CENTURY HOME SHOWCASING TIMELESS CURB APPEAL & A PRIVATE BACKYARD OASIS COMPLETE WITH AN INGROUND POOL! Welcome to this beautifully main

32 Photos

898 Yonge Street, Simcoe, ON , MLS #S13770588 , Image - 1

898 Yonge Street Midland, Simcoe, ON MLS® S13770588

Residential Freehold (Detached)

$649777.0

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

Welcome to 898 Yonge Street in Midland, perfect family home offering a functional layout, generous lot size, and a convenient location close to local

4 Photos

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

242 Barnett Avenue Midland, Simcoe, ON MLS® S13799500

Residential Freehold (Detached)

$510000.0

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

33 Photos

699 Aberdeen Boulevard, Simcoe, ON , MLS #S13659620 , Image - 1

Unit-901, 699 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13659620

Residential Condo & Other (Condo Apartment)

$899900.0

Price drop by 5.2%

2 +1 Beds
2 Baths
1800-1999 sq-ft

Stunning 1,919 sq. ft.2-bedroom plus den corner unit offers multiple walkouts and two private waterfront balconies. The bright open-concept layout fea

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

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