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Houses for Sale in Oro-Medonte ON Under $5 Million - P4

Showing results 91 - 120 of 156
Last Updated: December 05, 2025
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
23 Photos
Last Updated : 142 Days ago
1601 Penetanguishene Road, Simcoe, ON , MLS #40740637 , Image - 1
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1601 Penetanguishene Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40740637

Residential (Single Family Residence)

$699900
  • 3 Beds
  • 1 Baths
  • 1698 sq-ft
CHARMING COUNTRY HOME ON HALF AN ACRE WITH A STAYCATION-WORTHY BACKYARD! Looking for a home that’s got big country energy and a backyard that basicall
49 Photos
Last Updated : 142 Days ago
4 Clydesdale Court, Simcoe, ON , MLS #40745451 , Image - 1

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4 Clydesdale Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40745451

Residential (Single Family Residence)

$1799900
  • 4 Beds
  • 5 Baths
  • 3665 sq-ft
One-of-a-Kind in Braestone Estate Home with a Legal Coach Apartment! Welcome to 4 Clydesdale Court, a custom-designed estate-style home perfectly posi
50 Photos
Last Updated : 142 Days ago
6 Petherwin Place, Simcoe, ON , MLS #40746181 , Image - 1

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6 Petherwin Place Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40746181

Residential (Single Family Residence)

$1375000
  • 3 Beds
  • 3 Baths
  • 2800 sq-ft
WATERFRONT (137 feet)!!! Welcome to your dream retreat at 6 Petherwin Place, nestled on the serene shores of Bass Lake! This stunning 3-bedroom, 3-bat
47 Photos
Last Updated : 143 Days ago
13 Georgina Drive, Simcoe, ON , MLS #40738386 , Image - 1

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13 Georgina Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40738386

Residential (Single Family Residence)

$4500000
  • 3 Beds
  • 4 Baths
  • 3620 sq-ft
Exceptional Shoreline. Prestigious Location. Welcome to 13 Georgina Drive — a rare opportunity to own one of the most coveted lakefront properties on
36 Photos
Last Updated : 144 Days ago
1 Greenwood Forest Road, Simcoe, ON , MLS #40736004 , Image - 1

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1 Greenwood Forest Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40736004

Residential (Single Family Residence)

$1149000
price drop iconPrice drop by 11.2%
  • 3 Beds
  • 1 Baths
  • 954 sq-ft
Discover the charm of lakeside living at 1 Greenwood Forest Road in Oro-Medonte. This lovingly maintained, four-season cottage offers a peaceful retre
50 Photos
Last Updated : 144 Days ago
11 Sumac Crescent, Simcoe, ON , MLS #40744234 , Image - 1

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11 Sumac Crescent Sugarbush, Oro-Medonte, Simcoe, ON MLS® 40744234

Residential (Single Family Residence)

$975000
  • 4 Beds
  • 4 Baths
  • 2370 sq-ft
Welcome to 11 Sumac Crescent – A Comfortable & Character-Filled Family Home in Sugarbush, Oro-Medonte, this charming chalet-style home offers space, w
28 Photos
Last Updated : 144 Days ago
5305 Line 7 North, Simcoe, ON , MLS #40750902 , Image - 1

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5305 Line 7 North Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40750902

Residential (Single Family Residence)

$964900
  • 3 Beds
  • 3 Baths
  • 2596 sq-ft
Welcome to this beautifully appointed custom built 3-bedroom bungalow set on over 1.5 acres of private, forested land where peace, privacy, and stunni
44 Photos
Last Updated : 144 Days ago
8 Ash Court Court, Simcoe, ON , MLS #40728174 , Image - 1

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8 Ash Court Court Sugarbush, Oro-Medonte, Simcoe, ON MLS® 40728174

Residential (Single Family Residence)

$959000
price drop iconPrice drop by 1.1%
  • 4 Beds
  • 2 Baths
  • 1388 sq-ft
Welcome to Sugarbush, great community falling into the new school zone, being built at 4th line. This home will not disappoint at the end of a court o
34 Photos
Last Updated : 144 Days ago
9881 12 Highway, Simcoe, ON , MLS #40721523 , Image - 1

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9881 12 Highway Warminister, Oro-Medonte, Simcoe, ON MLS® 40721523

Residential (Single Family Residence)

$679900
price drop iconPrice drop by 2.9%
  • 3 Beds
  • 2 Baths
  • 1575 sq-ft
Welcome to 9881 Highway 12 in Warminster — a warm and inviting home just minutes from Orillia! This lovely side-split offers 3 bedrooms, 2 full bathro
40 Photos
Last Updated : 144 Days ago
32 Alpine Way, Simcoe, ON , MLS #40745828 , Image - 1

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32 Alpine Way Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40745828

Residential (Single Family Residence)

$1749000
  • 3 Beds
  • 3 Baths
  • 2360 sq-ft
Live where others vacation! Welcome to 32 Alpine Way in beautiful Horseshoe Valley, a four-season playground surrounded by nature, trails, and resort
44 Photos
Last Updated : 144 Days ago
1390 Warminster Sideroad, Simcoe, ON , MLS #40645210 , Image - 1

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1390 Warminster Sideroad Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40645210

Residential (Single Family Residence)

$1785000
price drop iconPrice drop by 20.7%
  • 3 Beds
  • 3 Baths
  • 2274 sq-ft
Act now to own this secluded 40-acre property located in the hills of Oro-Medonte Township between Orillia and Barrie. This property is ideal as an eq
47 Photos
Last Updated : 145 Days ago
24 Ironwood Trail, Simcoe, ON , MLS #40748028 , Image - 1

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24 Ironwood Trail Sugarbush, Oro-Medonte, Simcoe, ON MLS® 40748028

Residential (Single Family Residence)

$939000
  • 3 Beds
  • 3 Baths
  • 2519.21 sq-ft
Nestled in the highly sought-after Sugarbush community of Oro-Medonte, this beautifully maintained home sits on a spacious, tree-lined lot that offers
32 Photos
Last Updated : 145 Days ago
23 Owen Road, Simcoe, ON , MLS #40748945 , Image - 1

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23 Owen Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40748945

Residential (Single Family Residence)

$619900
  • 2 Beds
  • 1 Baths
  • 1181 sq-ft
*OVERVIEW* Charming Bungalow Located In A Great Neighbourhood of Oro-Medonte. Just Minutes To Barrie or Orillia and Only a 200 meter Walk To Lake Simc
30 Photos
Last Updated : 145 Days ago
33 Springhome Road, Simcoe, ON , MLS #40748791 , Image - 1

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33 Springhome Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40748791

Residential (Single Family Residence)

$1399900
  • 3 Beds
  • 3 Baths
  • 3572 sq-ft
ALL BRICK BUNGALOW WITH OVER 3,500 SQ FT ON 1.3 ACRES WITH A TRIPLE GARAGE, FINISHED WALKOUT BASEMENT & UPGRADES GALORE JUST STEPS FROM LAKE SIMCOE! T
24 Photos
Last Updated : 145 Days ago
5767 Line 3 North, Simcoe, ON , MLS #40750002 , Image - 1

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5767 Line 3 North Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40750002

Residential (Single Family Residence)

$849900
  • 3 Beds
  • 3 Baths
  • 2149 sq-ft
ESCAPE TO NATURE WITH THIS CHARMING BUNGALOW ON A ONE-ACRE LOT WITH A HEATED DETACHED DOUBLE CAR GARAGE! In the peaceful community of Moonstone, this
49 Photos
Last Updated : 145 Days ago
2020 5 Line N, Simcoe, ON , MLS #40726170 , Image - 1

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2020 5 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40726170

Residential (Single Family Residence)

$1999900
price drop iconPrice drop by 9.1%
  • 5 Beds
  • 3 Baths
  • 1950 sq-ft
Welcome to 2020 5th Line North in beautiful Oro-medonte a rare opportunity to enjoy the peace and privacy of country living on a spacious 1.377-acre
28 Photos
Last Updated : 145 Days ago
285 Warminster Sideroad, Simcoe, ON , MLS #40750122 , Image - 1

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285 Warminster Sideroad Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40750122

Residential (Single Family Residence)

$999999
  • 4 Beds
  • 3 Baths
  • 2437 sq-ft
2.7-ACRE PRIVATE RETREAT WITH A POOL, HOT TUB, FULLY RENOVATED INTERIOR & MAJOR UPDATES COMPLETE! Immerse yourself in the tranquillity of this 2.7-acr
39 Photos
Last Updated : 145 Days ago
10195 Hwy 12 West, Simcoe, ON , MLS #40749030 , Image - 1

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10195 Hwy 12 West Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40749030

Residential (Single Family Residence)

$2499900
  • 3 Beds
  • 3 Baths
  • 2112 sq-ft
A TRUE LIVE-WORK PROPERTY WITH A RETAIL STORE, OFFICE, MULTIPLE OUTBUILDINGS & OVER 95 ACRES TO GROW YOUR VISION! This picture-worthy property looks l
39 Photos
Last Updated : 145 Days ago
10195 Hwy 12 West, Simcoe, ON , MLS #40748989 , Image - 1

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Unit-C, 10195 Hwy 12 West Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40748989

Farm (Agriculture)

$3399900
  • 3 Beds
  • 3 Baths
  • 2112 sq-ft
ONLINE BUSINESS, HIGH-VISIBILITY LOCATION, RETAIL STORE, MULTIPLE OUTBUILDINGS & A CHARACTER-FILLED HOME! A once-in-a-lifetime chance to own a thrivin
50 Photos
Last Updated : 146 Days ago
2290 Highway 11 South, Simcoe, ON , MLS #40735080 , Image - 1

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2290 Highway 11 South Guthrie, Oro-Medonte, Simcoe, ON MLS® 40735080

Residential (Single Family Residence)

$725000
  • 4 Beds
  • 2 Baths
  • 1714 sq-ft
Charming 3+1 Bedroom, 2 Bath Home in Sought-After Oro-Medonte!Welcome to this well-maintained 1.5-storey detached home offering comfort, versatility,
50 Photos
Last Updated : 146 Days ago
3062 Townline Rr5 Line, Simcoe, ON , MLS #40733418 , Image - 1

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3062 Townline Rr5 Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40733418

Residential (Single Family Residence)

$1299000
price drop iconPrice drop by 5.5%
  • 4 Beds
  • 2 Baths
  • 2290 sq-ft
Welcome to 3062 Town Line — a picturesque Hallmark-style century home set on a scenic 2.59-acre lot. Blending timeless character with thoughtful updat
50 Photos
Last Updated : 147 Days ago
29 Nordic Trail, Simcoe, ON , MLS #40733715 , Image - 1

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29 Nordic Trail Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40733715

Residential (Single Family Residence)

$1269000
price drop iconPrice drop by 2.3%
  • 5 Beds
  • 3 Baths
  • 3004 sq-ft
*Overview* Welcome To 29 Nordic Trail, A Spacious And Versatile 5-Bedroom, 3-Bathroom Home Tucked Into The Heart Of Sought-After Horseshoe Valley. Bac
29 Photos
Last Updated : 147 Days ago
23 Conder Drive, Simcoe, ON , MLS #40749979 , Image - 1

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23 Conder Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40749979

Residential (Single Family Residence)

$699900
  • 3 Beds
  • 1 Baths
  • 1347 sq-ft
Welcome to 23 Conder Drive where country charm meets everyday convenience! Nestled on a beautifully treed 106 x 282 ft lot, this feel-good family home
50 Photos
Last Updated : 147 Days ago
11 Nevis Ridge Drive, Simcoe, ON , MLS #40749677 , Image - 1

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11 Nevis Ridge Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40749677

Residential (Single Family Residence)

$2499999
  • 6 Beds
  • 5 Baths
  • 5977 sq-ft
Prepare to be awestruck by this one-of-a-kind custom-built log home crafted from hand-peeled Western Red Cedar. Nestled on a private, tree-lined 2.1-a
49 Photos
Last Updated : 147 Days ago
11 Bunker Place, Simcoe, ON , MLS #40745597 , Image - 1

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11 Bunker Place Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40745597

Residential (Single Family Residence)

$1439000
  • 3 Beds
  • 3 Baths
  • 3447 sq-ft
An exceptionally spacious home, large private yard, grand interior spaces, making a true forever home in the heart of one of Ontario’s premier active-
50 Photos
Last Updated : 149 Days ago
25 Cathedral Pines Road, Simcoe, ON , MLS #40745262 , Image - 1

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25 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® 40745262

Residential (Single Family Residence)

$1085000
  • 3 Beds
  • 3 Baths
  • 1788 sq-ft
Welcome to 25 Cathedral Pines, a beautiful family home nestled in the heart of Horseshoe Valley—one of Ontario’s most sought-after destinations for ac
16 Photos
Last Updated : 149 Days ago
47 Campbell Avenue, Simcoe, ON , MLS #40748110 , Image - 1

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47 Campbell Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40748110

Residential (Single Family Residence)

$725000
  • 4 Beds
  • 2 Baths
  • 2725 sq-ft
ARCHITECTURAL MARVEL WITH OVER 2,700 SQFT OF UPDATED LIVING SPACE STEPS FROM LAKE SIMCOE! Step into something truly extraordinary with this one-of-a-k
39 Photos
Last Updated : 149 Days ago
2484 Highway 11 S, Simcoe, ON , MLS #40747195 , Image - 1

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2484 Highway 11 S Guthrie, Oro-Medonte, Simcoe, ON MLS® 40747195

Residential (Single Family Residence)

$1425000
  • 3 Beds
  • 1 Baths
  • 2255 sq-ft
LUXURY INSIDE, PARADISE OUTSIDE - THIS ONE WAS MADE TO ENTERTAIN! Live the lifestyle you’ve been dreaming of in this extraordinary home, set on a full
47 Photos
Last Updated : 149 Days ago
1 Best Court, Simcoe, ON , MLS #40745824 , Image - 1

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1 Best Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40745824

Residential (Single Family Residence)

$2450000
  • 4 Beds
  • 3 Baths
  • 4689 sq-ft
Tucked away on a quiet, prestigious court in Oro-Medonte is a home that captures what so many dream of, peace, space, and sunrises that take your brea
40 Photos
Last Updated : 149 Days ago
155 Parkside Drive, Simcoe, ON , MLS #40744518 , Image - 1

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155 Parkside Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40744518

Residential (Single Family Residence)

$1799000
  • 4 Beds
  • 3 Baths
  • 2949 sq-ft
Opportunity Awaits. Discover the best of lakefront living with 100' of pristine, clear waterfront on one of Oro-Medonte's most coveted streets.Enjoy q
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