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Houses for Sale in Midland ON Under $5 Million - P5

Showing results 121 - 146 of 146
Last Updated: November 07, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
42 Photos
Last Updated : 50 Days ago
179 Luckport Crescent, Simcoe, ON , MLS #S13190410 , Image - 1
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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
Last Updated : 53 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
37 Photos
Last Updated : 53 Days ago
699 Aberdeen Boulevard, Simcoe, ON , MLS #S13786440 , Image - 1

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Unit-706, 699 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13786440

Residential Condo & Other (Condo Apartment)

$624900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Discover the exceptional lifestyle offered at Tiffin Pier, a highly sought-after waterfront condominium community where the beauty of Georgian Bay is
27 Photos
Last Updated : 57 Days ago
158 Sixth Street, Simcoe, ON , MLS #S13775578 , Image - 1

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158 Sixth Street Midland, Simcoe, ON MLS® S13775578

Residential Freehold (Detached)

$549900.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 158 Sixth Street, a solidly built all-brick 2.5-storey home in Midland's desirable west end. Rich in character and charm, this inviting hom
40 Photos
Last Updated : 57 Days ago
1005 Dina Crescent, Simcoe, ON , MLS #S13478408 , Image - 1

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1005 Dina Crescent Midland, Simcoe, ON MLS® S13478408

Residential Freehold (Detached)

$714777.0
price drop iconPrice drop by 3.4%
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 1005 Dina Crescent in Midland, a beautifully maintained all-brick home offering space, comfort, and a fantastic location within walking dis
37 Photos
Last Updated : 58 Days ago
679 Montreal Street, Simcoe, ON , MLS #S13421928 , Image - 1

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679 Montreal Street Midland, Simcoe, ON MLS® S13421928

Residential Freehold (Duplex)

$645000.0
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Attention investors! Here is a rare, low-stress addition to your portfolio. Located in a desirable, high-demand neighborhood on Midland's west side, t
1 Photos
Last Updated : 59 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 : 60 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
32 Photos
Last Updated : 63 Days ago
699 ABERDEEN Boulevard, Simcoe, ON , MLS #S12492142 , Image - 1

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Unit-504, 699 ABERDEEN Boulevard Midland, Simcoe, ON MLS® S12492142

Residential Condo & Other (Condo Apartment)

$525000.0
price drop iconPrice drop by 7.7%
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
RARE TO FIND 1 BDRM,1 BATH,1 PARKING,1 LOCKER - IN THIS PRESTIGIOUS TIFFIN PIER CONDO LOCATED ON THE SHORE OF GEORGIAN BAY. 801 SQ F APARTMENT PLUS LA
12 Photos
Last Updated : 65 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 : 66 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,
28 Photos
Last Updated : 66 Days ago
519 Yonge Street, Simcoe, ON , MLS #S13624322 , Image - 1

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519 Yonge Street Midland, Simcoe, ON MLS® S13624322

Residential Freehold (Triplex)

$709900.0
price drop iconPrice drop by 5.3%
  • 6 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Investment Opportunity - Recently Renovated Triplex turnkey investment opportunity in the heart of town! This well-maintained triplex has seen extensi
4 Photos
Last Updated : 71 Days ago
637 Aberdeen Boulevard, Simcoe, ON , MLS #S13721708 , Image - 1
637 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13721708

Residential Freehold (Vacant Land)

$749900.0
Not often does a true waterfront lot become available in one of Midland's most prestigious communities. This exceptional property offers rare ownershi
32 Photos
Last Updated : 73 Days ago
756 Quebec Street, Simcoe, ON , MLS #S13715820 , Image - 1

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756 Quebec Street Midland, Simcoe, ON MLS® S13715820

Residential Freehold (Detached)

$539900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Charming two storey century home located in a quiet neighbourhood. Suitable for a small family or a retired couple looking to downsize. The main level
9 Photos
Last Updated : 75 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 : 85 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
26 Photos
Last Updated : 85 Days ago
423 Irwin Street, Simcoe, ON , MLS #S13670688 , Image - 1

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423 Irwin Street Midland, Simcoe, ON MLS® S13670688

Residential Freehold (Detached)

$679777.0
  • 4 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Welcome to 423 Irwin Street in Midland, a well-maintained all-brick home offering over 2,000 sq ft of finished living space in a quiet, family-friendl
34 Photos
Last Updated : 89 Days ago
867 Birchwood Drive, Simcoe, ON , MLS #S13660176 , Image - 1

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867 Birchwood Drive Midland, Simcoe, ON MLS® S13660176

Residential Freehold (Detached)

$549000.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 867 Birchwood Drive, a well-kept 3+1 bedroom bungalow situated on a desirable corner lot in Midland. The practical main-floor layout featur
40 Photos
Last Updated : 95 Days ago
329 Glenbrook Drive, Simcoe, ON , MLS #S13424482 , Image - 1

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329 Glenbrook Drive Midland, Simcoe, ON MLS® S13424482

Residential Freehold (Detached)

$998777.0
price drop iconPrice drop by 16.8%
  • 3 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 329 Glenbrook Drive in the prestigious area of Midland Point, one of Midland's most sought-after communities. Situated on a desirable corne
8 Photos
Last Updated : 102 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 : 102 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,
27 Photos
Last Updated : 121 Days ago
927 Vindin Street, Simcoe, ON , MLS #S13506250 , Image - 1

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927 Vindin Street Midland, Simcoe, ON MLS® S13506250

Residential Freehold (Detached)

$549777.0
  • 3 +0 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 927 Vindin Street in Midland, a rare opportunity to enjoy over two acres of privacy while still being centrally located and close to all am
1 Photos
Last Updated : 137 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
33 Photos
Last Updated : 148 Days ago
177 Southwinds Crescent, Simcoe, ON , MLS #S13126438 , Image - 1

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177 Southwinds Crescent Midland, Simcoe, ON MLS® S13126438

Residential Freehold (Att/Row/Townhouse)

$549777.0
  • 2 +1 Beds
  • 3 Baths
  • 700-1100 sq-ft
Welcome to 177 Southwinds Crescent in Midland, a well-maintained all-brick home located close to amenities, trails, marinas, and the beautiful shores
39 Photos
Last Updated : 163 Days ago
925 Dominion Avenue, Simcoe, ON , MLS #S13110226 , Image - 1

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925 Dominion Avenue Midland, Simcoe, ON MLS® S13110226

Residential Freehold (Detached)

$749777.0
  • 4 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to the perfect family home, where space, style, and comfort come together! Located in Midlands sought-after west end, this beautifully maintai
32 Photos
Last Updated : 186 Days ago
61 Riverwalk Place, Simcoe, ON , MLS #S13086446 , Image - 1

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61 Riverwalk Place Midland, Simcoe, ON MLS® S13086446

Residential Freehold (Detached)

$1130000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Luxurious Living with Backyard Oasis in Waterfront Community. Welcome to this exceptional 6-bedroom, 4-bathroom detached bungaloft, where timeless ele
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