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Houses for Sale in Southwest Middlesex ON Under $500K

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Are you looking for houses under $500k for sale in Southwest Middlesex ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Southwest Middlesex. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Southwest Middlesex. Whether you’re looking to buy houses under under $500k in Southwest Middlesex 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 Southwest Middlesex houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: September 28, 2026

22 Photos

22257 Pratt Siding Road W, Middlesex, ON , MLS #X13803662 , Image - 1

22257 Pratt Siding Road W Rural Southwest Middlesex, Southwest Middlesex, Middlesex, ON MLS® X13803662

Residential Freehold (Detached)

$399900.0

1 +2 Beds
1 Baths
1500-2000 sq-ft

Welcome to 22257 Pratt Siding Road, a country property set on approximately 1.2 acres surrounded by mature trees and established fruit trees. The prop

46 Photos

4838 Switzer Drive, Middlesex, ON , MLS #X13812760 , Image - 1

Unit-A4, 4838 Switzer Drive Rural Southwest Middlesex, Southwest Middlesex, Middlesex, ON MLS® X13812760

Residential Freehold (MobileTrailer)

$299900.0

3 Beds
2 Baths
700-1100 sq-ft

Rarely offered in Silver Dove Estates, this spacious 3-bedroom home provides the flexibility today's buyers are looking for. Whether you need space fo

33 Photos

150 O'Mara Street, Middlesex, ON , MLS #X13639622 , Image - 1

150 O'Mara Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13639622

Residential Freehold (Detached)

$449900.0

3 Beds
1 Baths
700-1100 sq-ft

Set on a beautifully maintained lot in a quiet, established pocket of Glencoe, this bungalow offers a lifestyle defined by relaxed elegance and effort

39 Photos

1825 Longwoods Drive, Middlesex, ON , MLS #X13773568 , Image - 1

1825 Longwoods Drive Wardsville, Southwest Middlesex, Middlesex, ON MLS® X13773568

Residential Freehold (Detached)

$429900.0

3 Beds
3 Baths
1500-2000 sq-ft

Small-town living, a beautifully renovated interior and nearly three-quarters of an acre to call your own. Welcome to 1825 Longwoods Road in Wardsvill

34 Photos

1792 Longwoods Road, Middlesex, ON , MLS #X13709668 , Image - 1

1792 Longwoods Road Wardsville, Southwest Middlesex, Middlesex, ON MLS® X13709668

Residential Freehold (Duplex)

$399900.0

2 +2 Beds
2 Baths
2000-2500 sq-ft

Looking for a smart way into homeownership while your tenant helps pay the mortgage? 1792 Longwoods Road is the turnkey duplex you've been waiting for

28 Photos

155 North Street, Middlesex, ON , MLS #X13760334 , Image - 1

155 North Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13760334

Residential Freehold (Detached)

$469000.0

4 Beds
1 Baths
1100-1500 sq-ft

A property with space, flexibility, and possibilities! Located in the heart of Glencoe, this charming home sits on a large lot with an abundance of ba

6 Photos

5857 Glendon Drive, Middlesex, ON , MLS #X13575242 , Image - 1

5857 Glendon Drive Rural Southwest Middlesex, Southwest Middlesex, Middlesex, ON MLS® X13575242

Residential Freehold (Vacant Land)

$399900.0

16.452 acres of A1-zoned land in rural Southwest Middlesex, offering a rare opportunity for the buyer looking for space, privacy, and recreational pot

50 Photos

3593 Concession Drive, Middlesex, ON , MLS #X13029230 , Image - 1

3593 Concession Drive Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13029230

Residential Freehold (Detached)

$485000.0

Price drop by 7.6%

4 Beds
3 Baths
1500-2000 sq-ft

2 houses on one lot -- Charming Bungaloft with In-Law Suite on a Spacious Lot in Glencoe! Welcome to this beautifully updated bungaloft set on a large

7 Photos

6506 Krista Lane, Middlesex, ON , MLS #X13516606 , Image - 1

6506 Krista Lane Rural Southwest Middlesex, Southwest Middlesex, Middlesex, ON MLS® X13516606

Residential Freehold (Vacant Land)

$379999.0

Price drop by 7.3%

Welcome to 6506 Krista Lane. This beautiful, flat 1.5 acre Rural Residential Lot is situated on a private street and awaits your vision of building a

19 Photos

186 VICTORIA Street, Middlesex, ON , MLS #X13722902 , Image - 1

186 VICTORIA Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13722902

Residential Freehold (Detached)

$399900.0

3 Beds
1 Baths
1100-1500 sq-ft

IMMEDIATE POSSESSION AVAILABLE! This updated 1.5 storey, 3 bedroom home offers a blend of charm and modern improvements. The new kitchen features new

22 Photos

176 KING Street, Middlesex, ON , MLS #X13006952 , Image - 1

176 KING Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13006952

Residential Freehold (Detached)

$369900.0

Price drop by 5.1%

3 Beds
2 Baths
1100-1500 sq-ft

First time buyers, downsizing, but big enough to accommodate a family, this 3 bedroom 1.5 bath, carpet free bungalow sits on a large 66'x 165' lot in

37 Photos

165 Victoria Street, Middlesex, ON , MLS #X13664318 , Image - 1

165 Victoria Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13664318

Residential Freehold (Detached)

$429900.0

3 Beds
1 Baths
1100-1500 sq-ft

Welcome to 165 Victoria Street Glencoe, a charming bungalow that offers far more space than meets the eye! Set on an impressive 99; x 165' fully fenc

10 Photos

22681 Thames Road, Middlesex, ON , MLS #X13621698 , Image - 1

22681 Thames Road Appin, Southwest Middlesex, Middlesex, ON MLS® X13621698

Residential Freehold (Vacant Land)

$350000.0

Discover the perfect foundation for your dream home on this beautifully improved 3.14 acre property. The lot has been thoughtfully prepared with major

6 Photos

Lots 28,29,30,31 Middlemiss Avenue, Middlesex, ON , MLS #X13611654 , Image - 1

Lots 28,29,30,31 Middlemiss Avenue Middlemiss, Southwest Middlesex, Middlesex, ON MLS® X13611654

Residential Freehold (Vacant Land)

$299900.0

ere is your chance to get out of the city and build your dream home on this 1.05 acre property in the community of Melbourne (Middlemiss). A short dri

1 Photos

4 Joann Street Middlemiss, Southwest Middlesex, Middlesex, ON MLS® X13553444

Residential Freehold (Vacant Land)

$329000.0

Discover The Ideal Property For Your Dream Home On This Spacious 0.595-Acre Corner Lot, Graced With Mature Trees That Provide Natural Beauty And Priva

7 Photos

112 VICTORIA Street, Middlesex, ON , MLS #X13582396 , Image - 1

112 VICTORIA Street Glencoe, Southwest Middlesex, Middlesex, ON MLS® X13582396

Residential Freehold (Vacant Land)

$200000.0

Build Your Dream Home in the Heart of Glencoe! This bright and sunny 65 x 156 ft flat building lot is ideally located in an established neighbourhood

30 Photos

21990 Hagerty Road, Middlesex, ON , MLS #X13166580 , Image - 1

21990 Hagerty Road Wardsville, Southwest Middlesex, Middlesex, ON MLS® X13166580

Residential Freehold (Detached)

$484900.0

Price drop by 11.7%

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

Welcome to this well-maintained raised bungalow, offering a perfect blend of comfort, style,and functionality. As you enter, you are greeted by a brig

3 Photos

237 Frederick Street W, Middlesex, ON , MLS #X12772688 , Image - 1

237 Frederick Street W Rural Southwest Middlesex, Southwest Middlesex, Middlesex, ON MLS® X12772688

Residential Freehold (Vacant Land)

$225000.0

This wooded parcel at 237 Frederick in Wardsville offers a serene and private setting, tucked away in a quiet location off the main road. Encompassing

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