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Detached Houses for Sale in Horseshoe Valley Oro-Medonte

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Last Updated: August 09, 2026

48 Photos

75 Cathedral Pines Road, Simcoe, ON , MLS #S13643948 , Image - 1

75 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13643948

Residential Freehold (Detached)

$945000.0

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

Located in the Cathedral Pines neighbourhood of Horseshoe Valley, 75 Cathedral Pines Drive is a robustly built early-1980s brick bungalow situated on

44 Photos

5 Pine Point, Simcoe, ON , MLS #S13521792 , Image - 1

5 Pine Point Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13521792

Residential Freehold (Detached)

$949000.0

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

Nestled on a quiet cul-de-sac in the sought-after Cathedral Pines community of Horseshoe Valley, this custom-built chalet-style bungalow is a rare off

41 Photos

7 Pine Spring N/A, Simcoe, ON , MLS #S13572222 , Image - 1

7 Pine Spring N/A Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13572222

Residential Freehold (Detached)

$799900.0

3 Beds
3 Baths
1500-2000 sq-ft

Calling outdoor enthusiasts! Mountain biking trails, hiking, snowshoeing, snowmobiling, skiing and golf right at your door step with this spectacular

39 Photos

26 Oakmont Avenue, Simcoe, ON , MLS #S13120274 , Image - 1

26 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13120274

Residential Freehold (Detached)

$969900.0

4 Beds
3 Baths
2000-2500 sq-ft

This beautiful 4-bedroom, 3-bathroom detached home is located just minutes away from Horseshoe Resort. The resort offers year-round activities such as

30 Photos

26 Cathedral Pines Road, Simcoe, ON , MLS #S13646460 , Image - 1

26 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13646460

Residential Freehold (Detached)

$1349000.0

5 Beds
5 Baths
2500-3000 sq-ft

TIMELESS ESTATE-STYLE LIVING IN DISTINGUISHED CATHEDRAL PINES WITH NEARLY 2,900 SQ FT ON OVER HALF AN ACRE! Hidden behind a veil of mature evergreens

46 Photos

16 Chestnut Lane, Simcoe, ON , MLS #S13457076 , Image - 1

16 Chestnut Lane Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13457076

Residential Freehold (Detached)

$1199900.0

2 +1 Beds
3 Baths
2000-2500 sq-ft

Experience refined single-level living in this custom Crown Point-built executive bungalow offering over 3,400 sq.ft. of finished living space, set on

45 Photos

12 Oakmont Avenue, Simcoe, ON , MLS #S13636814 , Image - 1

12 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13636814

Residential Freehold (Detached)

$839900.0

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

PRESENTING 12 Oakmont Avenue in the exceptional community of Horseshoe Valley, nestled in Simcoe County's Oro-Medonte - the perfect blend of recreatio

39 Photos

17 Bridle Path, Simcoe, ON , MLS #S13232422 , Image - 1

17 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13232422

Residential Freehold (Detached)

$1299999.0

Price drop by 1.9%

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to this stunning log-style chalet nestled in the heart of Horseshoe Valley, Oro-Medonte - one of Ontario's most sought-after four-season commu

50 Photos

18 Bridle Path, Simcoe, ON , MLS #S13632620 , Image - 1

18 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13632620

Residential Freehold (Detached)

$1249900.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

Discover refined bungalow living in the heart of prestigious Horseshoe Valley. With over 2,000 sq. ft. on the main level, this exceptional all brick c

Open House : Sun Aug 09, 12:00 PM to 02:00 PM

50 Photos

97 Highland Drive, Simcoe, ON , MLS #S13541312 , Image - 1

97 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13541312

Residential Freehold (Detached)

$1099000.0

4 +1 Beds
2 Baths
2000-2500 sq-ft

Remarkable ranch bungalow in prestigious Horseshoe Valley with generous 117 x 177 ft lot with ample lush privacy and plenty of trees. Wind up the ove

50 Photos

32 Valleycrest Drive, Simcoe, ON , MLS #S13157392 , Image - 1

32 Valleycrest Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13157392

Residential Freehold (Detached)

$938000.0

Price drop by 5.1%

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

Welcome to 32 Valleycrest Drive in Horseshoe Valley, a custom-built walkout bungalow nestled in the heart of the sought-after Highlands neighbourhood.

50 Photos

102 Highland Drive, Simcoe, ON , MLS #S13556736 , Image - 1

102 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13556736

Residential Freehold (Detached)

$1249900.0

3 +2 Beds
3 Baths
2000-2500 sq-ft

COVETED HORSESHOE VALLEY BUNGALOW WITH OVER 3,750 SQ FT, A WALKOUT BASEMENT, & A PRIVATE TREED BACKYARD! Buy the address for ski days, golf mornings,

30 Photos

46 Pine Ridge Trail, Simcoe, ON , MLS #S13597980 , Image - 1

46 Pine Ridge Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13597980

Residential Freehold (Detached)

$1225000.0

4 +1 Beds
3 Baths
2000-2500 sq-ft

Welcome to 46 Pine Ridge Trail in beautiful Horseshoe Valley. Located on one of the most sought after streets for mountain biking, cross country skii

50 Photos

18 Pine Lane, Simcoe, ON , MLS #S13572976 , Image - 1

18 Pine Lane Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13572976

Residential Freehold (Detached)

$1738000.0

4 +2 Beds
5 Baths
3000-3500 sq-ft

Fully renovated from kitchen to bathrooms to new mechanicals! Welcome to 18 Pine Lane in Horseshoe Valley, Oro-Medonte-a true character estate home th

46 Photos

16 Landscape Drive, Simcoe, ON , MLS #S13577476 , Image - 1

16 Landscape Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13577476

Residential Freehold (Detached)

$849900.0

3 +2 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Stunning sunlit bungalow backing onto lush greenspace with no neighbours behind, offering exceptional privac

37 Photos

11 Oakmont Avenue, Simcoe, ON , MLS #S13475644 , Image - 1

11 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13475644

Residential Freehold (Detached)

$829000.0

3 +2 Beds
4 Baths
1500-2000 sq-ft

MULTI-GENERATIONAL LIVING MEETS FOUR-SEASON HORSESHOE VALLEY ADVENTURE! Nearly 2,500 finished sq. ft. is only the beginning, with a finished lower lev

25 Photos

24 Birch Grove Drive, Simcoe, ON , MLS #S12916908 , Image - 1

24 Birch Grove Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12916908

Residential Freehold (Detached)

$1099000.0

Price drop by 12.1%

3 Beds
3 Baths
1500-2000 sq-ft

.Welcome to your perfect four-season home and retreat, just a stone's throw from the Horseshoe Valley Resort. Step inside to a bright, open-concept ma

42 Photos

47 Cathedral Pines Road, Simcoe, ON , MLS #S13249470 , Image - 1

47 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13249470

Residential Freehold (Detached)

$774900.0

Price drop by 3.0%

3 Beds
2 Baths
1500-2000 sq-ft

Welcome to Cathedral Pines, a sought after subdivision in Horseshoe Valley. Enjoy a fantastic view of the Valley from the back of this timber framed h

50 Photos

23 Country Club Lane, Simcoe, ON , MLS #S13020196 , Image - 1

23 Country Club Lane Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13020196

Residential Freehold (Detached)

$1178000.0

Price drop by 0.8%

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

Exceptional home backing onto a prestigious golf course and cross-country ski trails, offering a unique year-round lifestyle. Extensively renovated wi

44 Photos

16 Oakmont Avenue, Simcoe, ON , MLS #S13485848 , Image - 1

16 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13485848

Residential Freehold (Detached)

$929900.0

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

Fully Renovated From Top To Bottom In The Heart Of Horseshoe Valley! This Turnkey Home Features New Hardwood Flooring, Designer Lighting, Custom Featu

50 Photos

3 Nordic Trail, Simcoe, ON , MLS #S13465652 , Image - 1

3 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13465652

Residential Freehold (Detached)

$1362000.0

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

Exceptional space, exceptional privacy, and an exceptional location in the heart of one of Ontario's premier recreational communities. Welcome to 3 No

39 Photos

57 Highland Drive, Simcoe, ON , MLS #S13219996 , Image - 1

57 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13219996

Residential Freehold (Detached)

$1150000.0

Price drop by 4.2%

3 +1 Beds
4 Baths
2000-2500 sq-ft

Welcome to refined four-season living in the heart of Horseshoe Valley - one of Ontario's emerging Blue Zone inspired communities, where residents of

34 Photos

1 Pine Spring Road, Simcoe, ON , MLS #S13448576 , Image - 1

1 Pine Spring Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13448576

Residential Freehold (Detached)

$929000.0

3 Beds
4 Baths
2000-2500 sq-ft

Welcome to Horseshoe Valley living, where space, privacy, and four-season recreation come together beautifully. Set on a premium double lot surrounded

50 Photos

16 Highland Drive, Simcoe, ON , MLS #S13417362 , Image - 1

16 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13417362

Residential Freehold (Detached)

$1348000.0

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

Welcome to 16 Highland Drive in the sought-after Horseshoe Highlands of Oro-Medonte. This is a rare opportunity on the Highland Drive ridge, one of ju