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Detached Houses for Sale in Horseshoe Valley Oro-Medonte

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Last Updated: November 08, 2026

30 Photos

17 Fairway Court, Simcoe, ON , MLS #S14116238 , Image - 1

17 Fairway Court Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14116238

Residential Freehold (Detached)

$1449900.0

4 Beds
4 Baths
3500-5000 sq-ft

An Exceptional Luxury Retreat in Prestigious Horseshoe Highlands where refined elegance meets the beauty of nature! From the moment you step inside, y

46 Photos

16 Chestnut Lane, Simcoe, ON , MLS #S14093622 , Image - 1

16 Chestnut Lane Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14093622

Residential Freehold (Detached)

$1125000.0

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

EXCLUSIVE COURT LOCATION | EXECUTIVE BUNGALOW | HORSESHOE VALLEY | Experience refined single-level living in one of Horseshoe Valley's most coveted lo

Open House : Sun Nov 08, 01:00 PM to 03:00 PM

33 Photos

12 Nordic Trail, Simcoe, ON , MLS #S14153604 , Image - 1

12 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14153604

Residential Freehold (Detached)

$1170000.0

3 Beds
3 Baths
2000-2500 sq-ft

Completely reimagined in the heart of the prestigious Horseshoe Highlands! Set on an impressive 190-foot-deep lot measuring just under half an acre, t

Open House : Sun Nov 08, 12:00 PM to 02:00 PM

50 Photos

39 Landscape Drive, Simcoe, ON , MLS #S14027460 , Image - 1

39 Landscape Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14027460

Residential Freehold (Detached)

$989000.0

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

Ready for your next chapter? Discover the perfect blend of comfort, elegance and easy living at 39 Landscape Drive in the sought after Horseshoe Valle

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

Open House : Sun Nov 15, 10:00 AM to 04:00 PM

37 Photos

11 Oakmont Avenue, Simcoe, ON , MLS #S14081904 , Image - 1

11 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14081904

Residential Freehold (Detached)

$825000.0

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

50 Photos

3 Nordic Trail, Simcoe, ON , MLS #S14149772 , Image - 1

3 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14149772

Residential Freehold (Detached)

$1248000.0

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

30 Photos

13 Alpine Way, Simcoe, ON , MLS #S14141436 , Image - 1

13 Alpine Way Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14141436

Residential Freehold (Detached)

$1199000.0

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

This exceptional property offers the perfect setting for an active family who loves to embrace the outdoors and enjoy the very best of the four-season

49 Photos

2700 Line 4 N/A N, Simcoe, ON , MLS #S13854622 , Image - 1

2700 Line 4 N/A N Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13854622

Residential Freehold (Detached)

$1349900.0

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

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

SERENE COUNTRY LIVING - BEAUTIFULLY UPGRADED - EXQUISITE FINISHES - This home offers the rare combination of a country lifestyle and exceptional conve

Open House : Sun Nov 08, 01:00 PM to 03:00 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

50 Photos

44 HIGHLAND Drive, Simcoe, ON , MLS #S14084702 , Image - 1

44 HIGHLAND Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14084702

Residential Freehold (Detached)

$1599000.0

4 +1 Beds
4 Baths
3000-3500 sq-ft

Welcome to your home in paradise with all the luxurious extras you'd put on your wish-list! Home inspected, thumbs up! This heavenly, one acre parcel

Open House : Sun Nov 08, 01:00 PM to 03:00 PM

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

36 Photos

58 Highland Drive, Simcoe, ON , MLS #S14102764 , Image - 1

58 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14102764

Residential Freehold (Detached)

$1530000.0

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

Refined. Inviting. Elevated. Set in the sought-after community of Horseshoe Highlands, this custom-built bungalow pairs thoughtful design with quality

19 Photos

11 Pine Point, Simcoe, ON , MLS #S14093054 , Image - 1

11 Pine Point Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14093054

Residential Freehold (Detached)

$2599999.0

4 Beds
5 Baths
3500-5000 sq-ft

Top 5 Reasons You Will Love This Home: 1) Beautifully designed modern home by Thomas Tampold of Tampold Architects Inc. with interior design by Yorkvi

50 Photos

36 Highland Drive, Simcoe, ON , MLS #S14094654 , Image - 1

36 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14094654

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

39 Photos

17 Bridle Path, Simcoe, ON , MLS #S14093684 , Image - 1

17 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14093684

Residential Freehold (Detached)

$1199500.0

4 Beds
3 Baths
2000-2500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Fall in love with the timeless charm of this stunning home in prestigious Horseshoe Valley Highlands, featur

30 Photos

46 Pine Ridge Trail, Simcoe, ON , MLS #S13839158 , Image - 1

46 Pine Ridge Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13839158

Residential Freehold (Detached)

$1185000.0

Price drop by 1.1%

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 skiin

44 Photos

16 Oakmont Avenue, Simcoe, ON , MLS #S14009106 , Image - 1

16 Oakmont Avenue Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14009106

Residential Freehold (Detached)

$899000.0

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

A Masterpiece Renovation in the Heart of Horseshoe Valley. Every inch of this home has been meticulously reimagined from top to bottom and is truly mo

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

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

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