186+ Houses for Sale in Midland Under $5 Million

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67 Discovery Trail, Simcoe, ON , MLS #S13040164 , Image - 1

67 Discovery Trail Midland, Simcoe, ON MLS® S13040164

Residential Condo & Other (Semi-Detached Condo)

$524900.0

Price drop by 4.5%

2 Beds
4 Baths
1200-1399 sq-ft

'move in' ready, 5 year home. Just move in and enjoy. 60K in upgrades including Stainless steel appliances, home professionally painted, solid oak

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630 Manly Street, Simcoe, ON , MLS #S13689772 , Image - 1

630 Manly Street Midland, Simcoe, ON MLS® S13689772

Residential Freehold (Detached)

$644900.0

Price drop by 1.5%

3 Beds
2 Baths
1100-1500 sq-ft

Visit the REALTOR website for further information about this Listing. Beautifully Renovated 3-Bedroom Side-Split in a Desirable Family Neighbourhood.

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421 Midland Avenue, Simcoe, ON , MLS #S13736606 , Image - 1

421 Midland Avenue Midland, Simcoe, ON MLS® S13736606

Residential Freehold (Detached)

$699900.0

3 Beds
3 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Embrace the timeless appeal of a true century home, where a charming covered front porch, original character

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775 Ontario Street, Simcoe, ON , MLS #S13706024 , Image - 1

775 Ontario Street Midland, Simcoe, ON MLS® S13706024

Residential Freehold (Detached)

$599900.0

3 Beds
1 Baths
700-1100 sq-ft

Top 5 Reasons You Will Love This Home: 1) Step into the stunning, brand-new kitchen (2026), beautifully illuminated by natural light and showcasing cr

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372 Lakewood Drive, Simcoe, ON , MLS #S13752212 , Image - 1

372 Lakewood Drive Midland, Simcoe, ON MLS® S13752212

Residential Freehold (Detached)

$899000.0

3 Beds
2 Baths
1500-2000 sq-ft

Welcome to 372 Lakewood Drive - a sun-filled family home on Midland Bay where everyday life feels like a getaway.Tucked just steps from the water, thi

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305 Lindsay Street E, Simcoe, ON , MLS #S13749054 , Image - 1

305 Lindsay Street E Midland, Simcoe, ON MLS® S13749054

Residential Freehold (Detached)

$674900.0

Price drop by 90.0%

3 Beds
3 Baths
2000-2500 sq-ft

This 3 bedroom home sits on a 100' x 187' level lot with hedging all around the property for privacy. Thereis a large 20' x 20' storage shed at the ba

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699 ABERDEEN Boulevard, Simcoe, ON , MLS #S12492142 , Image - 1

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

Residential Condo & Other (Condo Apartment)

$525000.0

Price 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

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3282 Ogdens Beach Road, Simcoe, ON , MLS #S13067668 , Image - 1

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

Residential Freehold (Detached)

$174900.0

Price 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

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128 Ninth Street, Simcoe, ON , MLS #S13744450 , Image - 1

128 Ninth Street Midland, Simcoe, ON MLS® S13744450

Residential Freehold (Detached)

$599900.0

3 Beds
2 Baths
700-1100 sq-ft

Move-In Ready in West-End Midland! Welcome to 128 Ninth Street - a lovingly maintained 3-bedroom, 2-bathroom raised bungalow tucked away on a quiet st

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314 Bay Street, Simcoe, ON , MLS #S13746464 , Image - 1

314 Bay Street Midland, Simcoe, ON MLS® S13746464

Residential Freehold (Detached)

$429900.0

2 Beds
1 Baths
700-1100 sq-ft

A wonderful opportunity for first-time buyers or downsizers, this charming detached 2-bedroom home is move-in ready. From the moment you arrive, the i

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400 Keller Drive, Simcoe, ON , MLS #S13507026 , Image - 1

400 Keller Drive Midland, Simcoe, ON MLS® S13507026

Residential Freehold (Detached)

$874777.0

Price drop by 2.8%

4 +0 Beds
3 Baths
2500-3000 sq-ft

Welcome to 400 Keller Drive in Midland's desirable West end, an exceptional executive or family home ideally located close to all amenities, Little La

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361 Galloway Boulevard, Simcoe, ON , MLS #S13744284 , Image - 1

361 Galloway Boulevard Midland, Simcoe, ON MLS® S13744284

Residential Freehold (Detached)

$549900.0

3 Beds
3 Baths
1100-1500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Nestled on a quiet street in a highly sought-after family neighbourhood, this home delivers the perfect sett

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839 Sarah Boulevard, Simcoe, ON , MLS #S13503752 , Image - 1

839 Sarah Boulevard Midland, Simcoe, ON MLS® S13503752

Residential Condo & Other (Condo Townhouse)

$645900.0

Price drop by 4.3%

3 +1 Beds
3 Baths
1600-1799 sq-ft

Discover Exceptional Comfort and Effortless, Low Maintenance living in this unique condo with gorgeous natural water views tucked away in one of Midla

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379 Gloucester Street, Simcoe, ON , MLS #S13542010 , Image - 1

379 Gloucester Street Midland, Simcoe, ON MLS® S13542010

Residential Freehold (Detached)

$274777.0

Price 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

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1016 Wright Drive, Simcoe, ON , MLS #S13736826 , Image - 1

1016 Wright Drive Midland, Simcoe, ON MLS® S13736826

Residential Freehold (Semi-Detached )

$599900.0

3 Beds
3 Baths
1500-2000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Built in 2021 and thoughtfully upgraded throughout, this modern home showcases stylish flooring, central air

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280 Aberdeen Boulevard, Simcoe, ON , MLS #S13730886 , Image - 1

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!!

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836 Coral Springs Lane, Simcoe, ON , MLS #S13480740 , Image - 1

836 Coral Springs Lane Midland, Simcoe, ON MLS® S13480740

Residential Freehold (Att/Row/Townhouse)

$524777.0

Price drop by 2.8%

3 +0 Beds
2 Baths
700-1100 sq-ft

Welcome to 836 Coral Springs Lane - the perfect starter home or investment opportunity! This well-kept 3-bedroom, 2-bathroom home features an inviting

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469 Parkview Court, Simcoe, ON , MLS #S13741086 , Image - 1

469 Parkview Court Midland, Simcoe, ON MLS® S13741086

Residential Freehold (Detached)

$1149000.0

5 Beds
2 Baths
2000-2500 sq-ft

Welcome to the highly sought-after Midland Point community. This just under half acre lot has backyard access to the waterfront trail and Georgian Bay

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48 Northland Drive, Simcoe, ON , MLS #S13736382 , Image - 1

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,

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519 Yonge Street, Simcoe, ON , MLS #S13624322 , Image - 1

519 Yonge Street Midland, Simcoe, ON MLS® S13624322

Residential Freehold (Triplex)

$709900.0

Price 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

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958 Montreal Street, Simcoe, ON , MLS #S13731656 , Image - 1

958 Montreal Street Midland, Simcoe, ON MLS® S13731656

Residential Freehold (Duplex)

$644900.0

3 +2 Beds
3 Baths
1100-1500 sq-ft

***Legal Duplex with Vacant Possession or the Perfect Multigenerational Set Up!*** Opportunities like this in Midland's sought-after west end are incr

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449 Elizabeth Street, Simcoe, ON , MLS #S13731214 , Image - 1

449 Elizabeth Street Midland, Simcoe, ON MLS® S13731214

Residential Freehold (Detached)

$649000.0

3 Beds
3 Baths
1500-2000 sq-ft

WOW, this property checks a lot of boxes! If you're looking for a family home in a convenient location with great walkability to downtown and Little L

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66 Fifth Street, Simcoe, ON , MLS #S13707186 , Image - 1

66 Fifth Street Midland, Simcoe, ON MLS® S13707186

Residential Freehold (Detached)

$589900.0

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

Fresh. Inviting. Move-In Ready. Thoughtfully updated inside and out, this four-bedroom bungalow offers the perfect blend of comfort, functionality, an

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736 Victoria Street, Simcoe, ON , MLS #S13552932 , Image - 1

736 Victoria Street Midland, Simcoe, ON MLS® S13552932

Residential Freehold (Detached)

$849900.0

2 +2 Beds
2 Baths
1500-2000 sq-ft

Welcome to an exceptional in-town retreat where privacy, comfort and resort-style outdoor living come together. Set on an expansive, beautifully lands

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238 Sixth Street, Simcoe, ON , MLS #S13702204 , Image - 1

238 Sixth Street Midland, Simcoe, ON MLS® S13702204

Residential Freehold (Detached)

$649900.0

5 Beds
3 Baths
2000-2500 sq-ft

Step into the timeless charm of this beautifully maintained century home, offering the perfect blend of character, comfort, and versatility. Lovingly

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1010 Glen Eagles Crescent, Simcoe, ON , MLS #S13212784 , Image - 1

1010 Glen Eagles Crescent Midland, Simcoe, ON MLS® S13212784

Residential Freehold (Detached)

$579000.0

3 Beds
1 Baths
700-1100 sq-ft

Want a great location? This classic, 4-level backsplit has that and then some! Situated on a quieter crescent in an established neighbourhood of west-

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1059 Glen Mhor Crescent, Simcoe, ON , MLS #S13703630 , Image - 1

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,

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165 Wilson Road, Simcoe, ON , MLS #S13594232 , Image - 1

165 Wilson Road Midland, Simcoe, ON MLS® S13594232

Residential Freehold (Detached)

$1790000.0

3 +2 Beds
4 Baths
2500-3000 sq-ft

Every Once in awhile a Special Home comes along! This Modern Architectural Custom Built Bungalow Blends All The Current Luxuries You can Dream of In A

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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

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298 Seventh Street, Simcoe, ON , MLS #S13719098 , Image - 1

298 Seventh Street Midland, Simcoe, ON MLS® S13719098

Residential Freehold (Detached)

$889900.0

5 +1 Beds
5 Baths
3500-5000 sq-ft

Welcome to this spacious and versatile 5+1 bedroom, 4+1 bathroom home in Midland, offering an exceptional blend of space, functionality, and flexibili

Houses for Sale in Midland ON Under $5 Million - P4