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Oro-Medonte, ON Luxury Homes

Showing results 1 - 24 of 24

With Square Yards Canada, you can find your dream luxury homes for sale in Oro-Medonte. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Oro-Medonte

Last Updated: September 21, 2026

40 Photos

209 Bay Street, Simcoe, ON , MLS #S13508726 , Image - 1

209 Bay Street Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13508726

Residential Freehold (Detached)

$4490000.0

5 Beds
5 Baths
3000-3500 sq-ft

Rare Waterfront Estate in Prestigious Shanty BayA rare opportunity to own an exceptional waterfront retreat in the heart of Shanty Bay. Tucked away on

41 Photos

1359 Old Barrie Road E, Simcoe, ON , MLS #S13710136 , Image - 1

1359 Old Barrie Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13710136

Residential Freehold (Detached)

$2099900.0

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

Highest Quality From Top To Bottom Over 5000 SqFt Of Available Living Space, South Western Exposure Backyard For Beautiful Sunsets. One Of A Kind It F

42 Photos

13 Georgina Drive S, Simcoe, ON , MLS #S13801200 , Image - 1

13 Georgina Drive S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13801200

Residential Freehold (Detached)

$3149000.0

3 Beds
4 Baths
2000-2500 sq-ft

THE OPPORTUNITY IS NOW!!! 13 Georgina Drive is ready for its next chapter-THIS IS THE WATERFRONT YOU'VE BEEN WAITING FOR! Secure 120 FEET OF PRISTINE

48 Photos

1942 Ingram Road, Simcoe, ON , MLS #S13799822 , Image - 1

1942 Ingram Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13799822

Residential Freehold (Detached)

$2695000.0

4 Beds
5 Baths
3500-5000 sq-ft

This grand two story home has a walkout basement and 3 oversized garages. On 20 Acres Across From Copepland Forest. 2000Sq Ft Indoor Pool Room, with h

50 Photos

6 Georgian Grande Drive, Simcoe, ON , MLS #S13786564 , Image - 1

6 Georgian Grande Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13786564

Residential Freehold (Detached)

$2250000.0

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

OPEN HOUSE Sat Sept 19, 1-3pm. 6 Georgian Grande Drive is truly a one-of-a-kind home in the sought-after Braestone lifestyle community. Renovated with

50 Photos

24 Windfield Drive W, Simcoe, ON , MLS #S13752524 , Image - 1

24 Windfield Drive W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13752524

Residential Freehold (Detached)

$3250000.0

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

Welcome to this exceptional Scandinavian farmhouse-inspired residence on approximately 2.74 acres, ideally positioned on a lakeside cul-de-sac in the

40 Photos

3750 10 Line N, Simcoe, ON , MLS #S13787930 , Image - 1

3750 10 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13787930

Residential Freehold (Farm)

$4100000.0

4 Beds
4 Baths
1500-2000 sq-ft

A truly rare opportunity in Oro-Medonte. Set on 98 acres, this exceptional country property brings together everything people love about rural living:

46 Photos

42 Windfield Drive W, Simcoe, ON , MLS #S13767720 , Image - 1

42 Windfield Drive W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13767720

Residential Freehold (Detached)

$3899999.0

3 +2 Beds
4 Baths
5000 + sq-ft

An exceptional custom-built 5800 sqft private residence where no expense has been spared, showcasing the finest finishes inside and out and maintained

48 Photos

1304 Bass Lake Side Road N/A W, Simcoe, ON , MLS #S13677378 , Image - 1

1304 Bass Lake Side Road N/A W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13677378

Residential Freehold (Detached)

$2295000.0

5 Beds
5 Baths
2500-3000 sq-ft

Few properties do this much. On 20 acres in Oro-Medonte, this one is a family home, a hobby farm, a workshop and a four-season basecamp at once. The f

49 Photos

9 Barrie Terrace, Simcoe, ON , MLS #S13537858 , Image - 1

9 Barrie Terrace Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13537858

Residential Freehold (Detached)

$3699900.0

1 +3 Beds
3 Baths
3000-3500 sq-ft

Welcome to one of Barrie's most exceptional waterfront offerings. Nestled along the shores of Kempenfelt Bay on one of the city's most coveted streets

50 Photos

1290 A Line 15 N/A N, Simcoe, ON , MLS #S13739688 , Image - 1

1290 A Line 15 N/A N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13739688

Residential Freehold (Detached)

$2095000.0

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

Welcome to serene Bass Lake living at one of Oro-Medonte's most coveted waterfront locations. Nestled on a beautifully treed lot with direct lake acce

50 Photos

5385 8 Line N, Simcoe, ON , MLS #S13628286 , Image - 1

5385 8 Line N Moonstone, Oro-Medonte, Simcoe, ON MLS® S13628286

Residential Freehold (Detached)

$3399000.0

5 +2 Beds
6 Baths
5000 + sq-ft

FAMILY COMPOUND | Built in 2022, this expansive 9,000 sqft estate on 100 acres is ideal for multi-generational living, family compound use, or rental

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1450 Line 3 N/A N, Simcoe, ON , MLS #S13566402 , Image - 1

1450 Line 3 N/A N Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13566402

Residential Freehold (Detached)

$3699999.0

3 +3 Beds
5 Baths
3000-3500 sq-ft

Top 5 Reasons You Will Love This Home: 1) Set on 48 breathtaking acres in the highly sought-after Oro-Medonte, this exceptional custom-built ICF home

37 Photos

305 Bass Lake Side Road, Simcoe, ON , MLS #S13731008 , Image - 1

305 Bass Lake Side Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13731008

Residential Freehold (Detached)

$2599000.0

4 Beds
3 Baths
2500-3000 sq-ft

The Alexander Woodrow homestead built in 1903 is privately sited up a picturesque gated driveway surrounded by majestic maple trees and overlooking th

42 Photos

1189 Woodland Drive, Simcoe, ON , MLS #S13607388 , Image - 1

1189 Woodland Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13607388

Residential Freehold (Detached)

$2999900.0

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

Some properties offer waterfront. Others offer a lifestyle that simply can't be replicated. From the curb appeal to the breathtaking lake views the mo

50 Photos

11 Nevis Ridge Drive, Simcoe, ON , MLS #S13207526 , Image - 1

11 Nevis Ridge Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13207526

Residential Freehold (Detached)

$2100000.0

3 +3 Beds
5 Baths
3500-5000 sq-ft

Eleven Nevis Ridge is a rare Scandinavian scribe Western red cedar log home - a hand-fitted, one-of-a-kind retreat tucked at the end of a quiet cul-de

50 Photos

183 Lakeshore Road W, Simcoe, ON , MLS #S13628308 , Image - 1

183 Lakeshore Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13628308

Residential Freehold (Detached)

$2850000.0

4 Beds
7 Baths
3500-5000 sq-ft

Welcome to this exceptional luxury waterfront estate on Lake Simcoe, offering over 97 feet of private shoreline in sought-after Oro-Medonte. Ideally l

48 Photos

57 Alpine Drive, Simcoe, ON , MLS #S13576842 , Image - 1

57 Alpine Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13576842

Residential Freehold (Detached)

$2385000.0

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

Welcome to this stunning, new estate bungalow located in a quiet community just 5 minutes from a 36 slope ski resort and snowmobile trails. With quick

45 Photos

2533 Ridge Road W, Simcoe, ON , MLS #S13123868 , Image - 1

2533 Ridge Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13123868

Residential Freehold (Detached)

$15995000.0

5 Beds
6 Baths
3500-5000 sq-ft

Welcome to 2533 Ridge Road West - A Private Waterfront Sanctuary on Lake Simcoe. Discover an extraordinary opportunity to own a 17.5-acre private reso

50 Photos

2683 Lakeshore Road E, Simcoe, ON , MLS #S13137936 , Image - 1

2683 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13137936

Residential Freehold (Detached)

$2100000.0

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

Welcome to your private lakeside retreat on the serene shores of Carthew Bay. Perfectly positioned to capture Muskoka-like views, this exceptional wat

11 Photos

21 Pemberton Lane, Simcoe, ON , MLS #S13502654 , Image - 1

21 Pemberton Lane Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13502654

Residential Freehold (Other)

$24000000.0

5000 + sq-ft

* APPROVED REDEVELOPMENT *WATERFRONT*EQUESTRIAN Set Within The Coveted Stretch Known As Millionaires Row. Unlock The Full Potential Of Casa Lago Estat

35 Photos

1614 Ridge Road E, Simcoe, ON , MLS #S6142920 , Image - 1

1614 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S6142920

Residential Freehold (Multiplex)

$3299000.0

Price drop by 1.8%

6 Beds
5 Baths
5000 + sq-ft

Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This U

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P.LT 19 6 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12365883

Residential Freehold (Vacant Land)

$4200000.0

Price drop by 10.6%

Unbelievable Opportunity to Buy 90.32 Acres of Prime Land in Key Location. In An Established Area Of Private Residences And Backs Onto The Lake Simco

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Pt Lt 20 Concession 7 Road, Simcoe, ON , MLS #S12855250 , Image - 1

Pt Lt 20 Concession 7 Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12855250

Residential Freehold (Vacant Land)

$10000000.0

Attention Investors And Farmers! This Property Abuts The Lake Simcoe Regional Airport (Airport Allows Small Jets) 137 Acres Of Farm/Vacant Land. Curre

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