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Houses for Sale in Oro-Medonte ON Under $5 Million - P5

Showing results 121 - 150 of 156
Last Updated: December 05, 2025
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
50 Photos
Last Updated : 149 Days ago
35 Howard Drive, Simcoe, ON , MLS #40743867 , Image - 1
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35 Howard Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40743867

Residential (Single Family Residence)

$1099900
  • 4 Beds
  • 3 Baths
  • 2507 sq-ft
*OVERVIEW *Beautiful 2,500 sq ft two-storey family home in the desirable Harbourwood Community. Fully renovated in 2018 with modern finishes throughou
11 Photos
Last Updated : 149 Days ago
699 Moonstone Road E, Simcoe, ON , MLS #40740817 , Image - 1

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699 Moonstone Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40740817

Land (Residential)

$189900
DISCOVER A TRANQUIL 2.3-ACRE PROPERTY ALONG THE COLDWATER RIVER! This exceptional property offers 759 feet of shoreline along the picturesque Coldwate
50 Photos
Last Updated : 149 Days ago
6029 Line 6 North, Simcoe, ON , MLS #40740660 , Image - 1

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6029 Line 6 North Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40740660

Residential (Single Family Residence)

$1249000
  • 4 Beds
  • 2 Baths
  • 1481 sq-ft
Discover this charming Viceroy-built home featuring 4 bedrooms and 2 bathrooms, peacefully situated on a stunning 58-acre property. Surrounded by matu
27 Photos
Last Updated : 149 Days ago
978 15/16 Sideroad E Sideroad E, Simcoe, ON , MLS #40739076 , Image - 1

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978 15/16 Sideroad E Sideroad E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40739076

Residential (Single Family Residence)

$989900
  • 3 Beds
  • 1 Baths
  • 2357 sq-ft
Discover 978 15/16 Sideroad in picturesque Oro-Medonte Township. This stunning property offers the perfect blend of serene rural living and convenient
42 Photos
Last Updated : 149 Days ago
5789 4th Line N, Simcoe, ON , MLS #40738927 , Image - 1

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5789 4th Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40738927

Residential (Single Family Residence)

$1389000
  • 4 Beds
  • 2 Baths
  • 2650 sq-ft
Welcome to 5789 Line 4 N situated in the picturesque countryside within the township of Hillsdale. This stunning century farmhouse is the epitome of p
22 Photos
Last Updated : 149 Days ago
80 Horseshoe Boulevard, Simcoe, ON , MLS #40738137 , Image - 1

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Unit-503, 80 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40738137

Residential (Condo/Apartment Unit)

$540000
  • 2 Beds
  • 2 Baths
  • 1188 sq-ft
EXPERIENCE THE BEST OF HORSESHOE VALLEY LIVING! Experience year-round adventure and luxury living in this spectacular top-floor penthouse suite, perfe
8 Photos
Last Updated : 149 Days ago
17 Maple Ridge Rd, Simcoe, ON , MLS #40736426 , Image - 1

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17 Maple Ridge Rd Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40736426

Land (Residential)

$899900
UNLEASH YOUR IMAGINATION ON THIS INCREDIBLE 1.18-ACRE LOT IN A COVETED NEIGHBOURHOOD! Welcome to the perfect canvas for your future estate home locate
30 Photos
Last Updated : 149 Days ago
552 10 Line S, Simcoe, ON , MLS #40735503 , Image - 1

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552 10 Line S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40735503

Land (Residential)

$1249999
Discover the perfect blend of space, location, and potential with this expansive 96-acre parcel at 552 Line 10 S, Oro-Medonte. Situated less than a ki
50 Photos
Last Updated : 149 Days ago
102 Highland Drive, Simcoe, ON , MLS #40734662 , Image - 1

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102 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40734662

Residential (Single Family Residence)

$1399999
  • 5 Beds
  • 3 Baths
  • 4096 sq-ft
Luxury Living in a Coveted Location Welcome to 102 Highland Drive, Horseshoe Valley Nestled in one of Simcoe Countys most sought-after communities, t
7 Photos
Last Updated : 149 Days ago
197 Kennedy Avenue, Simcoe, ON , MLS #40733269 , Image - 1

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197 Kennedy Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40733269

Land (Residential)

$450000
BUILD YOUR DREAM JUST STEPS FROM LAKE SIMCOE ON THIS CLEARED 80 X 187 FT LOT! Unlock the potential of this incredible cleared residential lot just a s
9 Photos
Last Updated : 149 Days ago
39 & 43 Campbell Avenue, Simcoe, ON , MLS #40730878 , Image - 1

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39 & 43 Campbell Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40730878

Land (Residential)

$280000
Build Your Dream Escape – Prime Land Just Steps to Lake Simcoe!Discover the perfect canvas for your cabin or cottage retreat on this 1-acre treed parc
48 Photos
Last Updated : 149 Days ago
691 Mt St Louis Road Road W, Simcoe, ON , MLS #40730718 , Image - 1

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691 Mt St Louis Road Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40730718

Residential (Single Family Residence)

$2199000
  • 4 Beds
  • 2 Baths
  • 3338 sq-ft
Calling all skiers, nature enthusiasts and privacy seekers! This is the property for you. With over 10 acres of privacy, trees and trails it you won’t
11 Photos
Last Updated : 149 Days ago
8 Bensley Drive, Simcoe, ON , MLS #40730453 , Image - 1

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8 Bensley Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40730453

Residential (Mobile Home)

$294900
price drop iconPrice drop by 4.6%
  • 3 Beds
  • 1 Baths
  • 952 sq-ft
Welcome Home to this Fully Renovated 3 Bedroom, 1 Bath Mobile Home. Situated in Scenic Fergushill Estates. This Could Be the Perfect Opportunity to Do
2 Photos
Last Updated : 149 Days ago
17 Valleyview Drive, Simcoe, ON , MLS #40730114 , Image - 1
17 Valleyview Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40730114

Land (Residential)

$349900
Build your dream home on this fully treed lot in the Moonstone area of Oro-Medonte very close to Mount St. Louis ski hills and highway 400. This prop
43 Photos
Last Updated : 149 Days ago
9 Blueridge Crescent, Simcoe, ON , MLS #40730044 , Image - 1

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9 Blueridge Crescent Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40730044

Residential (Single Family Residence)

$2395000
price drop iconPrice drop by 4.0%
  • 4 Beds
  • 3 Baths
  • 2701 sq-ft
Welcome to 9 Blueridge Crescent, a rare and refined Lake Simcoe waterfront estate located on a quiet court in the prestigious community of Oro-Medonte
49 Photos
Last Updated : 149 Days ago
90 Highland Dr Drive, Simcoe, ON , MLS #40729880 , Image - 1

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Unit-2250, 90 Highland Dr Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40729880

Residential (Condo/Apartment Unit)

$694900
  • 2 Beds
  • 2 Baths
  • 1400 sq-ft
Welcome to your all-season retreat in the heart of Horseshoe Valley! This exceptional, fully furnished condo offers not just a place to stay but a com
40 Photos
Last Updated : 149 Days ago
23 Barrie Terrace, Simcoe, ON , MLS #40729560 , Image - 1

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23 Barrie Terrace Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40729560

Residential (Single Family Residence)

$1775000
  • 2 Beds
  • 1 Baths
  • 1300 sq-ft
More than meets the eye with this charming year-round cottage or home, nestled in the most exclusive waterfront enclave on the North Shore of Kempenfe
15 Photos
Last Updated : 149 Days ago
PT LOTS 23 & 24 Con 8, Simcoe, ON , MLS #40728794 , Image - 1

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PT LOTS 23 & 24 Con 8 Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40728794

Land (Residential)

$1750000
260 ACRES OF NATURAL BEAUTY WITH LIMITLESS POSSIBILITIES! Once in a lifetime, you are presented with a rare opportunity to own a remarkable 260-acre p
5 Photos
Last Updated : 149 Days ago
466 LINE 2 N/A Line, Simcoe, ON , MLS #40727384 , Image - 1
466 LINE 2 N/A Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40727384

Land (Mixed Use)

$695000
price drop iconPrice drop by 13.1%
New price! Motivated Seller. Build your dream home AND your dream shop! 5.9 acres being offered for sale with a section of the property zoned IR al
38 Photos
Last Updated : 149 Days ago
43 Thoroughbred Drive, Simcoe, ON , MLS #40726420 , Image - 1

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43 Thoroughbred Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40726420

Residential (Single Family Residence)

$1400000
  • 2 Beds
  • 2 Baths
  • 1722 sq-ft
Welcome to 43 Thoroughbred Drive in Oro-Medonte’s sought-after community of Braestone. AN ABSOLUTE MUST SEE! Situated on nearly one acre, this pristi
32 Photos
Last Updated : 149 Days ago
80 Horseshoe Valley Boulevard, Simcoe, ON , MLS #40724694 , Image - 1

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Unit-302, 80 Horseshoe Valley Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40724694

Residential (Condo/Apartment Unit)

$500000
price drop iconPrice drop by 4.8%
  • 2 Beds
  • 2 Baths
  • 1188 sq-ft
Year-Round Adventure Meets Modern Comfort in Horseshoe Valley! Discover the ultimate blend of relaxation and recreation in this beautifully appointed,
50 Photos
Last Updated : 149 Days ago
91 Lakeshore Road W, Simcoe, ON , MLS #40721480 , Image - 1

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91 Lakeshore Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40721480

Residential (Single Family Residence)

$2825000
price drop iconPrice drop by 3.4%
  • 4 Beds
  • 3 Baths
  • 3893 sq-ft
Immaculate once in a lifetime opportunity to be on Lake Simcoe's shores in this breathtaking ranch bungalow with bright walk-out lower level. With fo
47 Photos
Last Updated : 149 Days ago
4552 5th Line North Line, Simcoe, ON , MLS #40719253 , Image - 1

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4552 5th Line North Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40719253

Residential (Single Family Residence)

$1380000
  • 3 Beds
  • 3 Baths
  • 1907 sq-ft
Brand new custom dream home on a three-quarter acre estate lot with no neighbours behind you! This luxurious three bedroom executive bungalow is neari
27 Photos
Last Updated : 149 Days ago
791 Horseshoe Valley Road E, Simcoe, ON , MLS #40713078 , Image - 1

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791 Horseshoe Valley Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40713078

Farm (Agriculture)

$1850000
  • 5 Beds
  • 5 Baths
  • 3540 sq-ft
Discover a world of tranquility with this picturesque 80+ acre farm, perfect blend of modern living and rural serenity. The centrepiece of this estate
13 Photos
Last Updated : 149 Days ago
9 Beach Road, Simcoe, ON , MLS #40703935 , Image - 1

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9 Beach Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40703935

Land (Residential)

$639900
price drop iconPrice drop by 7.9%
Act now to own this private waterfront lot on Bass Lake, minutes west of Orillia and 75-minutes from the GTA. This is a rare opportunity to build your
43 Photos
Last Updated : 149 Days ago
90 Highland Drive, Simcoe, ON , MLS #40703325 , Image - 1

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Unit-2264, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40703325

Residential (Condo/Apartment Unit)

$479000
price drop iconPrice drop by 4.0%
  • 2 Beds
  • 2 Baths
  • 1281 sq-ft
Experience the perfect blend of comfort, adventure, and investment potential with this fully upgraded, furnished property. Whether you're looking for
13 Photos
Last Updated : 149 Days ago
2960 Line 8 N, Simcoe, ON , MLS #40701053 , Image - 1

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2960 Line 8 N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40701053

Land (Residential)

$699000
SERENE AND PRIVATE LOT JUST 30 MINUTES FROM BARRIE & 20 MINUTES FROM ORILLIA! Welcome to 2960 Line 8 North—your future dream property! This private, r
9 Photos
Last Updated : 149 Days ago
LOT 6 Holick Road, Simcoe, ON , MLS #40693097 , Image - 1

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LOT 6 Holick Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40693097

Land (Commercial)

$1874990
Prime Industrial Opportunity: Unlock potential with land already zoned for industrial use, with 50% lower land costs than Barrie and development charg
8 Photos
Last Updated : 149 Days ago
5477 Line 7 North Lane, Simcoe, ON , MLS #40657980 , Image - 1

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5477 Line 7 North Lane Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40657980

Land (Residential)

$1500000
First time on the market in over 200 years!!!!! Opportunity awaits. 10+ acre parcel ready to build your first dream home or better yet
18 Photos
Last Updated : 149 Days ago
LOT 39 Friesian Court, Simcoe, ON , MLS #40639068 , Image - 1

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LOT 39 Friesian Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40639068

Residential (Single Family Residence)

$2073900
  • 4 Beds
  • 4 Baths
  • 4291 sq-ft
Customized builder home under construction. ACT NOW! You still have time to choose all of your interior colours and materials. This home incorporates
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