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Houses Under $500K for Sale in Midland, ON

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Are you looking for houses under 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: March 22, 2025

15 Photos

34 Allison Lane, Simcoe, ON , MLS #40697334 , Image - 1

34 Allison Lane Midland, Simcoe, ON MLS® 40697334

Residential (Row/Townhouse)

$499,000

Price drop by 9.1%

2 Beds
3 Baths
1280 sq-ft

OPEN HOUSE SATURDAY MARCH 22nd & SUNDAY MARCH 23rd 11-12:30 PM. This newly built 2-bedroom, plus den, 2.5-bathroom Townhome in the sought-after Season

Open House : Sun Mar 23, 11:00 AM to 12:30 PM

23 Photos

42 Fourth Street, Simcoe, ON , MLS #S12034008 , Image - 1

42 Fourth Street Midland, Simcoe, ON MLS® S12034008

Residential Freehold (Detached)

$449,900

3 Beds
1 Baths
700-1100 sq-ft

Three bedroom bungalow in great central Midland location. Three bedrooms, four piece bath, kitchen and separate dining area, living room with walk out

21 Photos

778 William Street, Simcoe, ON , MLS #S12033762 , Image - 1

778 William Street Midland, Simcoe, ON MLS® S12033762

Residential Condo & Other (Condo Townhouse)

$479,000

3 Beds
2 Baths
1000-1199 sq-ft

Fully-finished and move-in ready, this 3-bed, 2 bath townhome has endless rooftop views from your main spaces and is neutrally painted throughout to u

39 Photos

411 Elizabeth Street, Simcoe, ON , MLS #S11936541 , Image - 1

411 Elizabeth Street Midland, Simcoe, ON MLS® S11936541

Residential Freehold (Detached)

$499,500

2 Beds
1 Baths

Charming 2 bedroom 1 bath home in the heart of Midland. Perfect for first time home buyers or downsizers. Step in to a large entry porch room with s

37 Photos

22 Allison Lane

22 Allison Lane Midland, Simcoe, ON MLS® S12031028

Residential Condo & Other (Condo Townhouse)

$499,900

1 Beds
2 Baths
1000-1199 sq-ft

22 Alison Lane offers a stylish and functional 1-bedroom + den, 2-bathroom layout in a well-appointed townhouse condo. Featuring an attached garage, t

21 Photos

280 Aberdeen Boulevard

280 Aberdeen Boulevard Midland, Simcoe, ON MLS® S12006534

Residential Condo & Other (Condo Apartment)

$424,000

1 Beds
1 Baths
600-699 sq-ft

Live carefree in your very own penthouse with spectacular views of Georgian Bay! Be literally steps from miles of waterfront trail for your outdoor en

33 Photos

335 RUSSELL Street, Simcoe, ON , MLS #S11959886 , Image - 1

335 RUSSELL Street Midland, Simcoe, ON MLS® S11959886

Residential Freehold (Semi-Detached )

$439,000

Price drop by 12.0%

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

***REDUCED $30,000*** Charming & Move-In Ready Home in Midland! Welcome to 335 Russell St, a beautifully updated and tastefully decorated home in a pr

15 Photos

34 Allison Lane, Simcoe, ON , MLS #S11968814 , Image - 1

34 Allison Lane Midland, Simcoe, ON MLS® S11968814

Residential Condo & Other (Condo Townhouse)

$499,000

Price drop by 9.1%

2 Beds
3 Baths
1200-1399 sq-ft

OPEN HOUSE SATURDAY MARCH 22nd & SUNDAY MARCH 23rd 11-12:30PM. This newly built 2-bedroom, plus den, 2.5-bathroom Townhome in the sought-after Seasons

9 Photos

722 Aberdeen Blvd, Simcoe, Ontario , MLS #S12014603 , Image - 1

722 Aberdeen Blvd Midland, Simcoe, ON MLS® S12014603

Residential (Vacant Land)

$382,500

Top 5 Reasons You Will Love This Property: 1) Craft your vision of coastal living on a pristine lot boasting panoramic views of Georgian Bay and one o

8 Photos

854 Yonge St, Simcoe, Ontario , MLS #S12008751 , Image - 1

854 Yonge St Midland, Simcoe, ON MLS® S12008751

Commercial (Sale Of Business)

$149,000

Excellent Opportunity to own and operate a well established LLBo licensed Indian Restaurant located at the busy intersection of Yonge St./penetanguish

34 Photos

3 Lakeshore Rd, Simcoe, Ontario , MLS #S11881242 , Image - 1

3 Lakeshore Rd Midland, Simcoe, ON MLS® S11881242

Residential (Mobile/Trailer)

$389,777

2 Beds
1 Baths
700-1100 sq-ft

Check this out! Time to sit back and relax. Lovely 2-Bedroom mobile home in sought after Smiths Camp. This mobile home features open concept living, d

22 Photos

280 Aberdeen Blvd

Unit-403-PH3, 280 Aberdeen Blvd Midland, Simcoe, ON MLS® S11942142

Condo (Condo Apartment)

$424,900

Price drop by 3.2%

1 Beds
1 Baths
600-699 sq-ft

This 1 bedroom and den condo boasts 9ft ceilings so go ahead and stretch out! Gorgeous waterfront views of Georgian Bay can be appreciated from your

11 Photos

740 Yonge St, Simcoe, Ontario , MLS #S11962744 , Image - 1

740 Yonge St Midland, Simcoe, ON MLS® S11962744

Commercial (Store W/Apartment/Office)

$499,900

Top 5 Reasons You Will Love This Property: 1) Formerly a restaurant with an upper level three bedroom and one bathroom apartment, this vacant property

5 Photos

450 Robert St, Simcoe, Ontario , MLS #S11971383 , Image - 1

450 Robert St Midland, Simcoe, ON MLS® S11971383

Residential (Vacant Land)

$249,777

Check this out. Prime Vacant Lot in the heart of Midland! This in-town lot is the perfect opportunity to build your dream home or investment income pr

10 Photos

788 Yonge St, Simcoe, Ontario , MLS #S9366239 , Image - 1

Unit-3, 788 Yonge St Midland, Simcoe, ON MLS® S9366239

Commercial (Sale Of Business)

Price On Request

Make your own Venture. Discover a prime restaurant opportunity in the bustling heart of Midland! This2,870 sq. ft. fully renovated space is an ideal s

18 Photos

195 Elizabeth St, Simcoe, Ontario , MLS #S11940817 , Image - 1

195 Elizabeth St Midland, Simcoe, ON MLS® S11940817

Residential (Detached)

$439,999

2 Beds
1 Baths

Experience The Awe-Inspiring Allure Of This Recently Remodelled Masterpiece Boasting A Vast Lot, Accompanied By A Fresh Roof Installed In 2022 Brand N

35 Photos

694 Quebec St, Simcoe, Ontario , MLS #S11972018 , Image - 1

694 Quebec St Midland, Simcoe, ON MLS® S11972018

Residential (Detached)

$449,999

3 Beds
1 Baths

Charming 3-bedroom home located in a convenient area just minutes from shopping and the waterfront. This inviting home features original hardwood floo

13 Photos

269 Whitfield Cres, Simcoe, Ontario , MLS #S10412006 , Image - 1

269 Whitfield Cres Midland, Simcoe, ON MLS® S10412006

Residential (Vacant Land)

$399,000

Rare 1.05 Acre Industrial Lot ( Zoned "M1" ) Within The Town Of Midland In The " Heritage Business Park " ! Unique Two Level Lot, Mostly Cleared And R

14 Photos

269 Whitfield Crescent, Simcoe, ON , MLS #S10412009 , Image - 1

269 Whitfield Crescent Midland, Simcoe, ON MLS® S10412009

Commercial (Land)

$399,000

Rare 1.05 Acre Industrial Lot ( Zoned M1) Within The Town Of Midland In The Heritage Business Park ! Unique Two Level Lot, Mostly Cleared And Ready

15 Photos

95 Fifth Street, Simcoe, ON , MLS #40673839 , Image - 1

95 Fifth Street Midland, Simcoe, ON MLS® 40673839

Residential Income (Duplex Side/Side)

$495,000

5 Beds
2 Baths
2115 sq-ft

Don't Miss Out on This Fantastic Investment Opportunity! This centrally located, Duplex in Midland offers versatility and potential.Featuring a spacio

13 Photos

95 Fifth St, Simcoe, Ontario , MLS #S10420836 , Image - 1

95 Fifth St Midland, Simcoe, ON MLS® S10420836

Residential (Duplex)

$495,000

5 Beds
3 Baths

Don't Miss Out on This Fantastic Investment Opportunity! This centrally located, Duplex in Midland offers versatility and potential. Featuring a spaci

3 Photos

293 Centennial Dr, Simcoe, Ontario , MLS #S11944192 , Image - 1

293 Centennial Dr Midland, Simcoe, ON MLS® S11944192

Residential (Vacant Land)

$339,000

WELCOME TO MARCELLUS PLACE, 4 VACANT LARGE LOTS, COMPLETELY CLEARED AND GRADED ON A PAVED CUL DU SAC ROAD. ALL INFRASTRUCTURE AND UTILITIES INSTALLED.

7 Photos

643 645 Dominion Ave, Simcoe, Ontario , MLS #S11945251 , Image - 1

643 645 Dominion Ave Midland, Simcoe, ON MLS® S11945251

Residential (Triplex)

$474,900

4 Beds
3 Baths
1500-2000 sq-ft

Fantastic Triplex with Unlimited Potential in Downtown Midland! Discover the possibilities with this remarkable triplex nestled in the heart of downto

4 Photos

699 Aberdeen Blvd

Unit-66, 699 Aberdeen Blvd Midland, Simcoe, ON MLS® S9263575

Commercial (Office)

$275,000

Work On the Water in Midlands Most Sought After Waterfront Community, With Loyal Clientele, Close to Downtown. Snowplowing, Garbage Removal, Bldg. Ins

24 Photos

555 Bay St, Simcoe, Ontario , MLS #S9362699 , Image - 1

555 Bay St Midland, Simcoe, ON MLS® S9362699

Commercial (Commercial/Retail)

$499,800

Excellent Opportunity for Investment! Ready to start your own restaurant? Restaurant set up or for prime retail or office space in a thriving location

3 Photos

815 King St, Simcoe, Ontario , MLS #S11899190 , Image - 1

Unit-123, 815 King St Midland, Simcoe, ON MLS® S11899190

Commercial (Sale Of Business)

$321,100

Amazing Business For Sale in Midland. Located at Very Busy, High Traffic Area and Popular Neighborhood of Midland, currently run by manager, best oppo

20 Photos

778 William Street, Simcoe, ON , MLS #40678962 , Image - 1

Unit-91, 778 William Street Midland, Simcoe, ON MLS® 40678962

Residential (Condo/Apartment Unit)

$399,500

3 Beds
1 Baths
1000 sq-ft

Discover the perfect blend of comfort, convenience, and affordability with this spacious 3-bedroom, 2-story condominium townhouse located in a vibrant

6 Photos

LOT 9 Cornell Drive, Simcoe, ON , MLS #40663747 , Image - 1

LOT 9 Cornell Drive Midland, Simcoe, ON MLS® 40663747

Land (Residential)

$299,000

20 Photos

9225 Hwy 93, Simcoe, Ontario , MLS #S9250417 , Image - 1

9225 Hwy 93 Midland, Simcoe, ON MLS® S9250417

Commercial (Sale Of Business)

$199,000

High performing licensed restaurant in Midland's Firth Corners shopping district that is located next to downtown Midland at Penetanguishene Rd and Yo

31 Photos

188 Sixth Street, Simcoe, ON , MLS #40642317 , Image - 1

188 Sixth Street Midland, Simcoe, ON MLS® 40642317

Residential (Single Family Residence)

$495,000

Price drop by 2.9%

3 Beds
1 Baths
1080 sq-ft

Welcome To 188 Sixth Street! This Charming Fully Detached Bungalow Is Located On A Quiet Street In The Heart Of Midland Featuring An Oversized Detache

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Rishi Raj Tiwari

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