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Houses for Sale in Midland ON Under $5 Million

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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: December 05, 2025

38 Photos

281 Puddicombe Road, Simcoe, ON , MLS #S12320852 , Image - 1

281 Puddicombe Road Midland, Simcoe, ON MLS® S12320852

Residential Freehold (Detached)

$1699900.0

3 Beds
4 Baths
2500-3000 sq-ft

Top 5 Reasons You Will Love This Home: 1) True gem located on a peninsula of the sheltered lee shore of Midland Bay, enjoying 260-degree of ever-chang

13 Photos

722 Aberdeen Boulevard, Simcoe, ON , MLS #S12464086 , Image - 1

722 Aberdeen Boulevard Midland, Simcoe, ON MLS® S12464086

Residential Freehold (Vacant Land)

$299900.0

< 700 sq-ft

Top 5 Reasons You Will Love This Property: 1) Build your dream of lakeside living on a pristine lot showcasing sweeping Georgian Bay views and overloo

26 Photos

993 Whitney Crescent, Simcoe, ON , MLS #S12456642 , Image - 1

993 Whitney Crescent Midland, Simcoe, ON MLS® S12456642

Residential Freehold (Detached)

$1149900.0

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

21 Photos

778 William Street, Simcoe, ON , MLS #S12476719 , Image - 1

Unit-56, 778 William Street Midland, Simcoe, ON MLS® S12476719

Residential Condo & Other (Condo Townhouse)

$375000.0

3 Beds
2 Baths
1200-1399 sq-ft

** OPEN HOUSE SUNDAY NOV 30TH 12-3PM** Welcome to this move-in ready Condo Townhouse in Midland, featuring 3 bedrooms and 2 bathrooms with a fully fin

30 Photos

467 Irwin Street, Simcoe, ON , MLS #S12389140 , Image - 1

467 Irwin Street Midland, Simcoe, ON MLS® S12389140

Residential Freehold (Detached)

$599900.0

3 Beds
2 Baths
700-1100 sq-ft

Welcome to this beautiful family home located on a quiet, tree-lined street in a sought-after neighborhood. This inviting residence offers the perfect

24 Photos

196 Fourth Street, Simcoe, ON , MLS #S12459858 , Image - 1

196 Fourth Street Midland, Simcoe, ON MLS® S12459858

Residential Freehold (Detached)

$515000.0

Price drop by 4.5%

3 Beds
2 Baths
1100-1500 sq-ft

Discover a rare in-town oasis where historic charm meets convenience. Step inside this beautiful 2-storey 3 bed 1.5 bath home, built over a century ag

37 Photos

155 William Street, Simcoe, ON , MLS #S12565904 , Image - 1

Unit-12, 155 William Street Midland, Simcoe, ON MLS® S12565904

Residential Condo & Other (Condo Apartment)

$1575000.0

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

Top 5 Reasons You Will Love This Condo: 1) Imagine waking up each morning to sweeping, uninterrupted views of Midland Harbour and the shimmering water

23 Photos

1041 Cook Drive, Simcoe, ON , MLS #S12562114 , Image - 1

1041 Cook Drive Midland, Simcoe, ON MLS® S12562114

Residential Freehold (Att/Row/Townhouse)

$495500.0

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to this beautifully cared-for 3-bedroom, 2-bathroom townhouse, ideally located in one of Midland's most desirable neighbourhoods. Move-in read

39 Photos

925 Dominion Avenue, Simcoe, ON , MLS #S12530096 , Image - 1

925 Dominion Avenue Midland, Simcoe, ON MLS® S12530096

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

34 Photos

381 Olive Street, Simcoe, ON , MLS #S12558602 , Image - 1

381 Olive Street Midland, Simcoe, ON MLS® S12558602

Residential Freehold (Detached)

$599900.0

2 Beds
2 Baths
700-1100 sq-ft

Welcome to 381 Olive Street in Midland - a unique opportunity zoned Industrial on nearly half an acre, offering exceptional versatility for home, hobb

18 Photos

9 Riverwalk Place, Simcoe, ON , MLS #S12544572 , Image - 1

9 Riverwalk Place Midland, Simcoe, ON MLS® S12544572

Residential Freehold (Detached)

$849900.0

3 Beds
3 Baths
1500-2000 sq-ft

Discover the charm of this sought-after enclave of Cape Cod-style homes nestled along the scenic shores of Georgian Bay in Midland. This stunning resi

29 Photos

828 Dominion Avenue, Simcoe, ON , MLS #S12414268 , Image - 1

828 Dominion Avenue Midland, Simcoe, ON MLS® S12414268

Residential Freehold (Detached)

$749900.0

3 +1 Beds
3 Baths
1500-2000 sq-ft

WEST END CHARMER WITH THOUGHTFUL UPDATES, A LEGAL SUITE WITH SEPARATE ENTRANCE, SPACIOUS INTERIOR, & SET ON A LARGE IN-TOWN LOT! You won't fully get t

47 Photos

635 Wayne Crescent, Simcoe, ON , MLS #S12246987 , Image - 1

635 Wayne Crescent Midland, Simcoe, ON MLS® S12246987

Residential Freehold (Detached)

$699000.0

Price drop by 2.8%

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

Welcome Home to 635 Wayne Cres Midland Ontario, This wonderful all brick raised bungalow is Available Now for you and your family. This Home offers 2

36 Photos

641 Bay Street, Simcoe, ON , MLS #S12516836 , Image - 1

641 Bay Street Midland, Simcoe, ON MLS® S12516836

Residential Freehold (Detached)

$659777.0

3 Beds
2 Baths
1100-1500 sq-ft

Welcome to your perfect family home, ideally situated in the heart of Midland. Just a short walk to shops, schools, trails, and the shores of beautifu

27 Photos

657 Manly Street, Simcoe, ON , MLS #S12512356 , Image - 1

657 Manly Street Midland, Simcoe, ON MLS® S12512356

Residential Freehold (Detached)

$665000.0

3 Beds
1 Baths
1500-2000 sq-ft

Welcome home to this well maintained home on a large, centrally located in town lot. There are no steps on this main floor including to the separate f

38 Photos

309 Manly Street, Simcoe, ON , MLS #S12509724 , Image - 1

309 Manly Street Midland, Simcoe, ON MLS® S12509724

Residential Freehold (Detached)

$424900.0

2 Beds
2 Baths
1100-1500 sq-ft

Welcome to 309 Manly Street in Midland. Whether you are looking for an investment or just starting out this property has upside potential. Featuring

32 Photos

61 Riverwalk Place, Simcoe, ON , MLS #S12309465 , Image - 1

61 Riverwalk Place Midland, Simcoe, ON MLS® S12309465

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

26 Photos

423 Irwin Street, Simcoe, ON , MLS #S12347563 , Image - 1

423 Irwin Street Midland, Simcoe, ON MLS® S12347563

Residential Freehold (Detached)

$699900.0

4 Beds
2 Baths
2000-2500 sq-ft

A Home That Fits Your Life, and Everyone in It. With four bedrooms, two full bathrooms, and a layout built for real comfort, this all-brick raised bun

20 Photos

14 Danielle Crescent, Simcoe, ON , MLS #S12206829 , Image - 1

14 Danielle Crescent Midland, Simcoe, ON MLS® S12206829

Residential Condo & Other (Semi-Detached Condo)

$549800.0

3 Beds
3 Baths
1400-1599 sq-ft

Visit REALTOR website for additional information. Nestled in Midland's The Seasons on Little Lake, this 1493 sq ft semi-detached condo offers accessib

35 Photos

296 John Street, Simcoe, ON , MLS #S12464734 , Image - 1

296 John Street Midland, Simcoe, ON MLS® S12464734

Residential Freehold (Detached)

$675000.0

3 +1 Beds
2 Baths
700-1100 sq-ft

Looking for a bungalow that offers 3+1 bedrooms, 2 bathrooms and a fully finished basement? Then look no further than this well maintained home locate

5 Photos

1203 Everton Road, Simcoe, ON , MLS #S12115568 , Image - 1

1203 Everton Road Midland, Simcoe, ON MLS® S12115568

Residential Freehold (Vacant Land)

$259000.0

Price drop by 3.7%

< 700 sq-ft

Attention all Builders & Investors. Amazing Vacant Lot!(109f X 250f) Minutes to Georgian Bay ( Midland Harbour) Walking distance to Bay Port . The Per

18 Photos

525 Midland Point Road, Simcoe, ON , MLS #S12447209 , Image - 1

Unit-36, 525 Midland Point Road Midland, Simcoe, ON MLS® S12447209

Residential Freehold (MobileTrailer)

$255000.0

2 Beds
1 Baths
700-1100 sq-ft

Easy living at its best in popular Leeshore Estates, Midland. This unit is located in Midland's prime waterfront community on Georgian Bay. Two bedroo

1 Photos

586 Dominion Avenue Midland, Simcoe, ON MLS® S12447186

Residential Freehold (Duplex)

$599000.0

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

This is a charming 4-bedroom, 4-bathroom, low maintenance duplex in a heart of downtown Midland. It's Within walking distance to all amenities, over 1

41 Photos

233 Queen Street, Simcoe, ON , MLS #S12446748 , Image - 1

233 Queen Street Midland, Simcoe, ON MLS® S12446748

Residential Freehold (Detached)

$599900.0

4 Beds
2 Baths
2000-2500 sq-ft

Welcome to 233 Queen Street, a charming century home offering timeless character, spacious living, and a prime location near Georgian Bay. Nestled on

14 Photos

269 Whitfield Crescent, Simcoe, ON , MLS #S12443929 , Image - 1

269 Whitfield Crescent Midland, Simcoe, ON MLS® S12443929

Residential Freehold (Vacant Land)

$335900.0

< 700 sq-ft

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

44 Photos

330 Third Street, Simcoe, ON , MLS #S12443761 , Image - 1

330 Third Street Midland, Simcoe, ON MLS® S12443761

Residential Freehold (Detached)

$499000.0

2 Beds
2 Baths
700-1100 sq-ft

Charming Century Home in the Heart of Midland! Perfect for First-Time Buyers & Young Families! Step into this beautifully renovated and immaculately c

26 Photos

659 Victoria Street, Simcoe, ON , MLS #S12222561 , Image - 1

659 Victoria Street Midland, Simcoe, ON MLS® S12222561

Residential Freehold (Detached)

$485000.0

Price drop by 3.0%

2 Beds
1 Baths
700-1100 sq-ft

This well-maintained 2-bedroom, 1-bath bungalow is move-in ready and perfectly suited for first-time buyers, down-sizers, or anyone looking for a low-

34 Photos

3 Lakeshore Road, Simcoe, ON , MLS #S12213140 , Image - 1

3 Lakeshore Road Midland, Simcoe, ON MLS® S12213140

Residential Freehold (MobileTrailer)

$389777.0

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

18 Photos

204 Gianetto Drive, Simcoe, ON , MLS #S12205970 , Image - 1

204 Gianetto Drive Midland, Simcoe, ON MLS® S12205970

Residential Freehold (Vacant Land)

$214000.0

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

7 Photos

607 TAYLOR Drive, Simcoe, ON , MLS #S12161574 , Image - 1

607 TAYLOR Drive Midland, Simcoe, ON MLS® S12161574

Residential Freehold (Vacant Land)

$250000.0

Price drop by 16.4%

< 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

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