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Oro-Medonte, ON Luxury Homes

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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: November 05, 2026

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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

Open House : Sat Nov 07, 02:30 PM to 04:30 PM

42 Photos

13 Georgina Drive S, Simcoe, ON , MLS #S14145888 , Image - 1

13 Georgina Drive S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14145888

Residential Freehold (Detached)

$2995000.0

3 Beds
4 Baths
2000-2500 sq-ft

Rare waterfront opportunity on Kempenfelt Bay with immediate occupancy available! Discover an exceptional opportunity to own 120 feet of beautiful wat

47 Photos

247 Lakeshore Road W, Simcoe, ON , MLS #S13829078 , Image - 1

247 Lakeshore Road W Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13829078

Residential Freehold (Detached)

$5999500.0

4 Beds
5 Baths
3500-5000 sq-ft

If Lake Simcoe had a front row, this would be it. Set on 1.09 private acres along Lake Simcoe's prestigious North Shore, 247 Lakeshore Rd West pairs 9

Open House : Sat Nov 07, 01:30 PM to 03:00 PM

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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

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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

24 Windfield Drive W, Simcoe, ON , MLS #S13838544 , Image - 1

24 Windfield Drive W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13838544

Residential Freehold (Detached)

$2998888.0

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:

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

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

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

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

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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

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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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Oro-Medonte, ON Luxury Homes

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