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Houses for Sale in Horseshoe Valley Oro-Medonte Under $500K

Showing results 1 - 16 of 16

Looking for houses under $500k for sale in Horseshoe Valley, Oro-Medonte? With Square Yards Canada, discover a vast range of properties within your budget in Horseshoe Valley across Toronto. If you plan to buy houses under $500k in Horseshoe Valley, Oro-Medonte, you can refine your search by property size, specific amenities, and property age. Filter the listings by the number of bedrooms, bathrooms, and surface area to match your requirements. Our listings feature a wide range of Horseshoe Valley houses for sale under $500k, including freehold properties, condos, and commercial spaces.

Last Updated: November 05, 2026

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1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S14120756 , Image - 1

Unit-224, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14120756

Residential Condo & Other (Condo Apartment)

$345000.0

1 +0 Beds
1 Baths
500-599 sq-ft

Whether you're seeking a full-time home, weekend retreat, recreational getaway, or investment property, this turnkey condo chalet offers an exceptiona

27 Photos

90 Highland Drive, Simcoe, ON , MLS #S14104710 , Image - 1

Unit-2094-2095, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14104710

Residential Condo & Other (Condo Apartment)

$414750.0

2 Beds
2 Baths
1400-1599 sq-ft

Two living spaces. One unique opportunity in Horseshoe Valley. This spacious 2-bedroom, 2-bathroom condo offers a versatile two-residence configuratio

24 Photos

90 Highland Drive, Simcoe, ON , MLS #S13519786 , Image - 1

Unit-2010/2011, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13519786

Residential Condo & Other (Condo Apartment)

$390000.0

Price drop by 6.0%

2 Beds
2 Baths
1200-1399 sq-ft

Improved price! Live, work. play, profit! Welcome to resort style living at Horseshoe. This amazing unit in the Hansom building offers the rare abilit

11 Photos

90 Highland Drive, Simcoe, ON , MLS #S13701426 , Image - 1

Unit-2296-2297, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13701426

Residential Condo & Other (Condo Apartment)

$415000.0

Price drop by 9.0%

2 Beds
2 Baths
1400-1599 sq-ft

Whether you're searching for a place to call home or a smart addition to your investment portfolio, this versatile property offers exceptional flexibi

16 Photos

90 Highland Drive, Simcoe, ON , MLS #S14029628 , Image - 1

Unit-2290, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14029628

Residential Condo & Other (Condo Apartment)

$388500.0

2 +2 Beds
2 Baths
1200-1399 sq-ft

Unique Two-Unit Condominium in Horseshoe Valley - 90 Highland Drive is an exceptional opportunity for investors or homeowners looking to generate rent

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90 Highland Drive, Simcoe, ON , MLS #S13739786 , Image - 1

Unit-2252-2253, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13739786

Residential Condo & Other (Condo Apartment)

$449000.0

Price drop by 18.4%

2 Beds
2 Baths
1400-1599 sq-ft

Welcome to 2252-53 90 Highland Dr in Carriage Hills, Horseshoe Valley-a fully furnished, turnkey four-season condo offering approximately 1,400 sq ft

37 Photos

40 Horseshoe Boulevard, Simcoe, ON , MLS #S14100118 , Image - 1

Unit-Suite 206, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14100118

Residential Condo & Other (Condo Apartment)

$399900.0

2 Beds
2 Baths
600-699 sq-ft

Welcome to Horseshoe Valley! Whether you're looking for a Year-Round Home or the Perfect Vacation Retreat, this inviting Condo in Copeland House offer

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40 HORSESHOE Boulevard, Simcoe, ON , MLS #S13736152 , Image - 1

Unit-302, 40 HORSESHOE Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13736152

Residential Condo & Other (Condo Apartment)

$397900.0

Price drop by 0.3%

1 +1 Beds
2 Baths
700-799 sq-ft

VACANT, PRICED TO SELL!**FOUR-SEASON GETAWAY WITH SKI HILL VIEWS, COVERED BALCONY, PARKING & LOCKER!** One-bedroom plus den layout in 756 sq. ft. with

12 Photos

3 Valleycrest Drive, Simcoe, ON , MLS #S13800950 , Image - 1

3 Valleycrest Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13800950

Residential Freehold (Vacant Land)

$475000.0

Top 5 Reasons You Will Love This Property: 1) Fully serviced building lot offering an exciting opportunity to bring your vision to life with essential

41 Photos

90 Highland Drive, Simcoe, ON , MLS #S13876096 , Image - 1

Unit-2328/2329, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13876096

Residential Condo & Other (Condo Apartment)

$431750.0

2 Beds
2 Baths
1400-1599 sq-ft

Some properties offer a getaway. This one offers options. Set within Highland Estate in the heart of Horseshoe Valley, this furnished residence combin

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19 Birch Grove Drive, Simcoe, ON , MLS #S12995486 , Image - 1

19 Birch Grove Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12995486

Residential Freehold (Vacant Land)

$449000.0

Price drop by 8.2%

Have you ever dreamed of living in a place where you can walk to the tee-box or the chairlifts? Welcome to 19 Birch Grove Drive, a rare opportunity to

43 Photos

1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S13862678 , Image - 1

Unit-312, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13862678

Residential Condo & Other (Condo Townhouse)

$369000.0

2 Beds
2 Baths
1200-1399 sq-ft

Updated condo in the heart of the Horseshoe Valley. Across the street from Horseshoe Resort and The Heights ski hill. Siding onto Copeland forest over

10 Photos

90 Highland Drive, Simcoe, ON , MLS #S13723826 , Image - 1

Unit-2014/15, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13723826

Residential Condo & Other (Condo Townhouse)

$406000.0

2 Beds
2 Baths
1200-1399 sq-ft

Tucked away in the heart of Horseshoe Valley, this unique property at 90 Highland Drive delivers the ultimate blend of lifestyle and income potential.

14 Photos

80 Horseshoe Boulevard, Simcoe, ON , MLS #S13659946 , Image - 1

Unit-403, 80 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13659946

Residential Condo & Other (Condo Apartment)

$439999.0

Price drop by 4.3%

2 +1 Beds
2 Baths
1000-1199 sq-ft

Breathtaking Views At The Heart of Horseshoe Resort. Ideal For Year Round Residence, Vacation Home Or Option To Be Apart of Resort's Rental Program. B

32 Photos

40 Horseshoe Boulevard, Simcoe, ON , MLS #S13801576 , Image - 1

Unit-107, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13801576

Residential Condo & Other (Condo Apartment)

$431000.0

1 +1 Beds
2 Baths
700-799 sq-ft

**RARE GROUND-FLOOR MOUNTAIN-VIEW SUITE AT HORSESHOE RESORT!** Imagine waking up to beautiful ski hill views, stepping directly onto your private gard

6 Photos

1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S13234932 , Image - 1

Unit-309, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13234932

Residential Condo & Other (Condo Apartment)

$364999.0

Price drop by 2.7%

2 Beds
1 Baths
1200-1399 sq-ft

A Place To Get Away Or Stay. Welcome To The Heart Of Horseshoe Valley, Where Four-Season Recreation, Natural Beauty, And Resort-Style Amenities Come

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