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

Showing results 31 - 60 of 66
Last Updated: September 26, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
23 Photos
Last Updated : 15 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
40 Photos
Last Updated : 15 Days ago
680 Ontario Street, Simcoe, ON , MLS #S13602160 , Image - 1

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680 Ontario Street Midland, Simcoe, ON MLS® S13602160

Residential Freehold (Detached)

$465000.0
price drop iconPrice drop by 2.1%
  • 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
3 Photos
Last Updated : 17 Days ago
725 Aberdeen Boulevard, Simcoe, ON , MLS #S13436118 , Image - 1
Unit-57, 725 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13436118

Residential Condo & Other (Vacant Land Condo)

$27500.0
  • 0-499 sq-ft
30 Foot Marina Boat Slip. Rare opportunity to purchase a slip on beautiful GEORGIAN BAY why pay for a seasonal rental at a Marina. Can you even find a
1 Photos
Last Updated : 17 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 : 18 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
9 Photos
Last Updated : 21 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)

$174900.0
price drop iconPrice drop by 7.9%
  • 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
28 Photos
Last Updated : 22 Days ago
379 Gloucester Street, Simcoe, ON , MLS #S13542010 , Image - 1

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379 Gloucester Street Midland, Simcoe, ON MLS® S13542010

Residential Freehold (Detached)

$274777.0
price drop iconPrice drop by 8.3%
  • 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
12 Photos
Last Updated : 23 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 : 24 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,
29 Photos
Last Updated : 28 Days ago
1059 Glen Mhor Crescent, Simcoe, ON , MLS #S13703630 , Image - 1

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1059 Glen Mhor Crescent Midland, Simcoe, ON MLS® S13703630

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 1059 Glen Mhor Crescent, a home that offers something buyers are always searching for but rarely find at this price point: space, privacy,
17 Photos
Last Updated : 30 Days ago
21 Vics Road, Simcoe, ON , MLS #S13551836 , Image - 1

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21 Vics Road Midland, Simcoe, ON MLS® S13551836

Residential Freehold (MobileTrailer)

$229900.0
price drop iconPrice drop by 8.0%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Looking for an affordable starter home or the perfect place to retire? Welcome to 21 Vic's Road! This 3-bedroom, 1-bathroom home is nestled on a rare,
29 Photos
Last Updated : 31 Days ago
79 Stans Circle, Simcoe, ON , MLS #S13709426 , Image - 1

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79 Stans Circle Midland, Simcoe, ON MLS® S13709426

Residential Freehold (MobileTrailer)

$109990.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Enjoy breathtaking views of Little Lake, complemented by a spacious private yard, ideal for relaxation and o
9 Photos
Last Updated : 33 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
21 Photos
Last Updated : 33 Days ago
817 Birchwood Drive, Simcoe, ON , MLS #S13536666 , Image - 1

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817 Birchwood Drive Midland, Simcoe, ON MLS® S13536666

Residential Freehold (Detached)

$489000.0
price drop iconPrice drop by 2.0%
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
This 3+1 bedroom, 2 bath bungalow offers the perfect combination of comfort, functionality, and versatility in a desirable Midland neighbourhood. The
29 Photos
Last Updated : 36 Days ago
525 Midland Point Road, Simcoe, ON , MLS #S13699776 , Image - 1

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Unit-33, 525 Midland Point Road Midland, Simcoe, ON MLS® S13699776

Residential Freehold (MobileTrailer)

$229900.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Here's why 525 Midland Point Road Unit #33 could be your next move -- AFFORDABLE, EASY LIVING STEPS FROM GEORGIAN BAY -- BRIGHT & MOVE-IN READY - Fres
35 Photos
Last Updated : 38 Days ago
778 William Street, Simcoe, ON , MLS #S13690416 , Image - 1

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Unit-58, 778 William Street Midland, Simcoe, ON MLS® S13690416

Residential Condo & Other (Condo Townhouse)

$399900.0
  • 3 +1 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Fantastic opportunity for first-time buyers, downsizers, or anyone looking for an easy-to-maintain home wit
30 Photos
Last Updated : 40 Days ago
10 Maple Lane, Simcoe, ON , MLS #S13247166 , Image - 1

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10 Maple Lane Midland, Simcoe, ON MLS® S13247166

Residential Freehold (MobileTrailer)

$244000.0
price drop iconPrice drop by 6.1%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Clean, cozy, and move in ready. This bright and tidy 2 bedroom mobile home offers comfortable, affordable living in the heart of Smith's Camp. Enjoy
7 Photos
Last Updated : 43 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
28 Photos
Last Updated : 43 Days ago
375 Horrell Avenue, Simcoe, ON , MLS #S13674652 , Image - 1

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375 Horrell Avenue Midland, Simcoe, ON MLS® S13674652

Residential Freehold (Detached)

$449777.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 375 Horrell Avenue in Midland, a great opportunity for first-time buyers, investors, or those looking for an affordable home in a convenien
8 Photos
Last Updated : 60 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 : 60 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,
18 Photos
Last Updated : 68 Days ago
204 Gianetto Drive, Simcoe, ON , MLS #S12628254 , Image - 1

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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
5 Photos
Last Updated : 80 Days ago
560 Taylor Drive, Simcoe, ON , MLS #S13540070 , Image - 1
560 Taylor Drive Midland, Simcoe, ON MLS® S13540070

Residential Freehold (Vacant Land)

$229900.0
Opportunity to secure one of the last remaining lots in Midlands most sought-after waterfront community. This rare permit ready lot opens up to 80' at
3 Photos
Last Updated : 85 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
12 Photos
Last Updated : 86 Days ago
601 Taylor Drive, Simcoe, ON , MLS #S13512648 , Image - 1

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601 Taylor Drive Midland, Simcoe, ON MLS® S13512648

Residential Freehold (Vacant Land)

$299900.0
Top 5 Reasons You Will Love This Property: 1) Steps from the sparkling shores of Georgian Bay, with the property backing onto Tiffin Pier Lake, offeri
11 Photos
Last Updated : 86 Days ago
595 Taylor Drive, Simcoe, ON , MLS #S13512600 , Image - 1

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595 Taylor Drive Midland, Simcoe, ON MLS® S13512600

Residential Freehold (Vacant Land)

$299900.0
Top 5 Reasons You Will Love This Property: 1) Exceptional location near Georgian Bay featuring partial water views and backing onto the tranquil water
11 Photos
Last Updated : 86 Days ago
565 Taylor Drive, Simcoe, ON , MLS #S13512566 , Image - 1

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565 Taylor Drive Midland, Simcoe, ON MLS® S13512566

Residential Freehold (Vacant Land)

$299900.0
Top 5 Reasons You Will Love This Property: 1)Last available walk-out lot in this prestigious waterfront neighbourhood, offering a rare opportunity to
11 Photos
Last Updated : 86 Days ago
589 Taylor Drive, Simcoe, ON , MLS #S13512522 , Image - 1

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589 Taylor Drive Midland, Simcoe, ON MLS® S13512522

Residential Freehold (Vacant Land)

$299900.0
Top 5 Reasons You Will Love This Property: 1) Steps from Georgian Bay, offering an unmatched lifestyle surrounded by natural beauty and waterfront cha
1 Photos
Last Updated : 95 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
5 Photos
Last Updated : 110 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
Shortlisted Properties
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