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Detached Houses for Sale in Horseshoe Valley Oro-Medonte

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Last Updated: September 23, 2026

33 Photos

12 Nordic Trail, Simcoe, ON , MLS #S13801332 , Image - 1

12 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13801332

Residential Freehold (Detached)

$1248000.0

3 Beds
3 Baths
2000-2500 sq-ft

Imagine finding a wonderful home in a dream location then discovering it needs about $300,000 in upgrades...Now imagine finding a wonderful home in a

Open House : Sun Sep 27, 11:00 AM to 01:00 PM

46 Photos

16 Chestnut Lane, Simcoe, ON , MLS #S13731496 , Image - 1

16 Chestnut Lane Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13731496

Residential Freehold (Detached)

$1199900.0

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

Experience refined single-level living in one of Horseshoe Valley's most coveted locations - an exclusive private quiet court showcasing the premier l

50 Photos

36 Highland Drive, Simcoe, ON , MLS #S13816496 , Image - 1

36 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13816496

Residential Freehold (Detached)

$1399900.0

3 Beds
3 Baths
2000-2500 sq-ft

Nestled in prestigious Horseshoe Valley, this spectacular custom-built bungalow sits on a private, beautifully landscaped 1.73-acre estate surrounded

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

Open House : Sun Sep 27, 12:00 PM to 02:00 PM

39 Photos

17 Bridle Path, Simcoe, ON , MLS #S13811192 , Image - 1

17 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13811192

Residential Freehold (Detached)

$1239999.0

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

Open House : Sat Oct 03, 12:00 PM to 02:00 PM

42 Photos

47 Cathedral Pines Road, Simcoe, ON , MLS #S13767640 , Image - 1

47 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13767640

Residential Freehold (Detached)

$749900.0

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

36 Photos

6 BOVILLE Court, Simcoe, ON , MLS #S13792898 , Image - 1

6 BOVILLE Court Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13792898

Residential Freehold (Detached)

$949000.0

4 +0 Beds
3 Baths
2000-2500 sq-ft

Live the Horseshoe Valley lifestyle in this beautifully positioned family home, tucked away on a quiet cul-de-sac with a private wooded backdrop and n

50 Photos

32 Valleycrest Drive, Simcoe, ON , MLS #S13765630 , Image - 1

32 Valleycrest Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13765630

Residential Freehold (Detached)

$938000.0

2 +1 Beds
3 Baths
1500-2000 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

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)

$1278000.0

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

41 Photos

7 Pine Spring N/A, Simcoe, ON , MLS #S13786340 , Image - 1

7 Pine Spring N/A Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13786340

Residential Freehold (Detached)

$749900.0

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

57 Highland Drive, Simcoe, ON , MLS #S13742900 , Image - 1

57 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13742900

Residential Freehold (Detached)

$1099999.0

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

Welcome to refined four-season living in the heart of Horseshoe Valley-an emerging Blue Zone inspired community where an active, healthy lifestyle com

30 Photos

13 Alpine Way, Simcoe, ON , MLS #S13742930 , Image - 1

13 Alpine Way Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13742930

Residential Freehold (Detached)

$1250000.0

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

Set in the heart of Horseshoe Valley, within an exclusive enclave of fine homes, this exceptional property offers a lifestyle many consider a true Blu

50 Photos

3 Nordic Trail, Simcoe, ON , MLS #S13674818 , Image - 1

3 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13674818

Residential Freehold (Detached)

$1280000.0

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

40 Photos

9 Bridle Path, Simcoe, ON , MLS #S13757332 , Image - 1

9 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13757332

Residential Freehold (Detached)

$1399900.0

3 +1 Beds
4 Baths
2500-3000 sq-ft

This home offers the rare combination of serene country living and exceptional convenience, nestled on a picturesque, tree-lined lot just minutes from

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)

$1198000.0

Price drop by 2.2%

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

34 Alpine Way, Simcoe, ON , MLS #S13737344 , Image - 1

34 Alpine Way Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13737344

Residential Freehold (Detached)

$1395000.0

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

Live where other people come to recreate. This well-maintained square-log bungaloft with a post-and-beam interior captures the four-season Horseshoe V

26 Photos

4 Boville Court, Simcoe, ON , MLS #S13731876 , Image - 1

4 Boville Court Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13731876

Residential Freehold (Detached)

$892000.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 4 Boville Court, where comfort, space, and nature come together to create the perfect year-round retreat. Ideally located just minutes from

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

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

49 Photos

2700 Line 4 N/A N, Simcoe, ON , MLS #S13223608 , Image - 1

2700 Line 4 N/A N Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13223608

Residential Freehold (Detached)

$1399900.0

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

Welcome To Your Private Hillside Retreat In The Heart Of Horseshoe Valley. Set On Over 6 Acres And Perched Beautifully Above The Surrounding Landscape

1 Photos

15 Birch Grove Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13709216

Residential Freehold (Detached)

$978000.0

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

Walk to the chairlifts! Walk to the tee box! Walk to the trails! Walk to the restaurants! Luxe resort style living in this beautiful four bedroom chal

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

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

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

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