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Houses for Sale in Midland ON Under $500K - P2

Showing results 31 - 57 of 57
Last Updated: November 11, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
31 Photos
Last Updated : 26 Days ago
390 Mildred Street, Simcoe, ON , MLS #S13811184 , Image - 1
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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
23 Photos
Last Updated : 26 Days ago
77 Stans Circle, Simcoe, ON , MLS #S13761402 , Image - 1

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77 Stans Circle Midland, Simcoe, ON MLS® S13761402

Residential Freehold (MobileTrailer)

$105900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Enjoy a large kitchen and living space that seamlessly adjoins to an outdoor deck, perfect for hosting guest
13 Photos
Last Updated : 26 Days ago
722 Aberdeen Boulevard, Simcoe, ON , MLS #S13805682 , Image - 1

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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
28 Photos
Last Updated : 27 Days ago
137 Fourth Street, Simcoe, ON , MLS #S13809860 , Image - 1

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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
27 Photos
Last Updated : 29 Days ago
328 Third Street, Simcoe, ON , MLS #S14007024 , Image - 1

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328 Third Street Midland, Simcoe, ON MLS® S14007024

Residential Freehold (Detached)

$485000.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Have you been dreaming of a character home in sought-after west end Midland? Well look no further than this well-appointed Third Street charmer betwee
3 Photos
Last Updated : 33 Days ago
420 Cornell Drive, Simcoe, ON , MLS #S13520162 , Image - 1
420 Cornell Drive Midland, Simcoe, ON MLS® S13520162

Residential Freehold (Vacant Land)

$189000.0
Prime West End Building Lot on a quiet, lakeside Cul-de-Sac in Midland, ON. The perfect blend of tranquil living & Georgian Bay lifestyle. This beaut
4 Photos
Last Updated : 34 Days ago
242 Barnett Avenue, Simcoe, ON , MLS #S13799500 , Image - 1
242 Barnett Avenue Midland, Simcoe, ON MLS® S13799500

Residential Freehold (Detached)

$469000.0
price drop iconPrice drop by 8.0%
  • 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
24 Photos
Last Updated : 36 Days ago
179 Seventh Street, Simcoe, ON , MLS #S13824824 , Image - 1

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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
5 Photos
Last Updated : 36 Days ago
720 Ontario Street, Simcoe, ON , MLS #S12874628 , Image - 1
720 Ontario Street Midland, Simcoe, ON MLS® S12874628

Residential Freehold (Vacant Land)

$100000.0
With R3 zoning in place, this site offers flexibility for residential development under the Town of Midland's zoning framework, supporting a range of
5 Photos
Last Updated : 36 Days ago
309 Penetanguishene Road, Simcoe, ON , MLS #S12876860 , Image - 1
309 Penetanguishene Road Midland, Simcoe, ON MLS® S12876860

Residential Freehold (Vacant Land)

$275000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a infill lot, close to hospital, schools
5 Photos
Last Updated : 36 Days ago
305 Penetanguishene Rd Road, Simcoe, ON , MLS #S12876730 , Image - 1
305 Penetanguishene Rd Road Midland, Simcoe, ON MLS® S12876730

Residential Freehold (Vacant Land)

$250000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a building lot, close to hospital, schoo
5 Photos
Last Updated : 36 Days ago
301 Penetanguishene Road, Simcoe, ON , MLS #S12876542 , Image - 1
301 Penetanguishene Road Midland, Simcoe, ON MLS® S12876542

Residential Freehold (Vacant Land)

$225000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a infill lot, close to hospital, schools
5 Photos
Last Updated : 36 Days ago
1041 Ingram Crescent, Simcoe, ON , MLS #S12876230 , Image - 1
1041 Ingram Crescent Midland, Simcoe, ON MLS® S12876230

Residential Freehold (Vacant Land)

$275000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a building lot, close to hospital, schoo
5 Photos
Last Updated : 36 Days ago
1037 Ingram Crescent, Simcoe, ON , MLS #S12875954 , Image - 1
1037 Ingram Crescent Midland, Simcoe, ON MLS® S12875954

Residential Freehold (Vacant Land)

$300000.0
Unique deep lot ! Subject to site plan and municipal approvals, tons of flexibility for residential development under the Town of Midland's zoning fra
6 Photos
Last Updated : 36 Days ago
611 William Street, Simcoe, ON , MLS #S12875640 , Image - 1

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611 William Street Midland, Simcoe, ON MLS® S12875640

Residential Freehold (Vacant Land)

$160000.0
Requires Official Plan Act amendment from current Natural Heritage designation. Possibly a zoning change depending on development strategy. Registere
9 Photos
Last Updated : 41 Days ago
3282 Ogdens Beach Road, Simcoe, ON , MLS #S13067668 , Image - 1

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Unit-62, 3282 Ogdens Beach Road Midland, Simcoe, ON MLS® S13067668

Residential Freehold (Detached)

$169900.0
price drop iconPrice drop by 10.5%
  • 3 Beds
  • 1 Baths
  • < 700 sq-ft
End of season promotion original retail $219,865 Current In-Stock Price: $189,900Featured Cottage Event Price: $174,900. Nestled on an interior w
37 Photos
Last Updated : 50 Days ago
320 Scott Street, Simcoe, ON , MLS #S13772898 , Image - 1

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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
26 Photos
Last Updated : 57 Days ago
346 Bay Street, Simcoe, ON , MLS #S13783804 , Image - 1

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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
1 Photos
Last Updated : 63 Days ago
239 Marshall Road, Simcoe, ON
239 Marshall Road Midland, Simcoe, ON MLS® S13761598

Residential Freehold (Vacant Land)

Price On Request
Attention Investors, Builders & Hobby Farmers! Rare opportunity to own approximately 32 acres of corner lot at 239 Marshall Dr, Midland. This property
49 Photos
Last Updated : 64 Days ago
16 Samantha Lane, Simcoe, ON , MLS #S13727986 , Image - 1

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16 Samantha Lane Midland, Simcoe, ON MLS® S13727986

Residential Condo & Other (Condo Townhouse)

$449900.0
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to modern, maintenance-free living in this beautifully designed condo semi-detached home built in 2020! With everything - from the structure t
12 Photos
Last Updated : 69 Days ago
280 Aberdeen Boulevard, Simcoe, ON , MLS #S13730886 , Image - 1

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Unit-415, 280 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13730886

Residential Condo & Other (Condo Apartment)

$399900.0
  • 2 Beds
  • 1 Baths
  • 600-699 sq-ft
Penthouse overlooking Georgian Bay, anyone? If you have ever wanted a condominium with a large balcony and water views, this may be the one for you!!
29 Photos
Last Updated : 70 Days ago
48 Northland Drive, Simcoe, ON , MLS #S13736382 , Image - 1

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48 Northland Drive Midland, Simcoe, ON MLS® S13736382

Residential Freehold (MobileTrailer)

$259900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
MOTIVATED SELLER! A great opportunity to downsize your home and move into this clean and comfortable mobile home in Midland. Located in Smith's Camp,
9 Photos
Last Updated : 79 Days ago
696 King Street, Simcoe, ON , MLS #S13697204 , Image - 1

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Unit-72, 696 King Street Midland, Simcoe, ON MLS® S13697204

Residential Condo & Other (Condo Townhouse)

$450000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
This end-unit condo bungalow offers 2 bedrooms, 2 full bathrooms and convenient main level living in a well-maintained Midland community. The layout i
7 Photos
Last Updated : 89 Days ago
607 TAYLOR Drive, Simcoe, ON , MLS #S13677582 , Image - 1

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607 TAYLOR Drive Midland, Simcoe, ON MLS® S13677582

Residential Freehold (Vacant Land)

$179900.0
  • < 700 sq-ft
Build Your Dream Home Here. Rare opportunity to own a spacious building lot (60ft Wide x 229ft Deep) backing onto Tiffin Pond in a very desirable Midl
8 Photos
Last Updated : 106 Days ago
418 Dominion Avenue, Simcoe, ON , MLS #S13445334 , Image - 1

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418 Dominion Avenue Midland, Simcoe, ON MLS® S13445334

Residential Freehold (Detached)

$499990.0
price drop iconPrice 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
Last Updated : 106 Days ago
354 Midland Avenue, Simcoe, ON , MLS #S13436614 , Image - 1

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354 Midland Avenue Midland, Simcoe, ON MLS® S13436614

Residential Freehold (Detached)

$399990.0
price drop iconPrice 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,
1 Photos
Last Updated : 141 Days ago
458 93 Highway, Simcoe, ON
458 93 Highway Midland, Simcoe, ON MLS® S13479456

Residential Freehold (Vacant Land)

$389000.0
Excellent opportunity to acquire vacant land in the growing community of Penetanguishene. Conveniently located close to all amenities, including shopp
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