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Houses for Sale in Oro-Medonte ON Under $1.5 Million - P4

Showing results 91 - 120 of 176
Last Updated: November 11, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
10 Photos
Last Updated : 16 Days ago
13 Windfield Drive W, Simcoe, ON , MLS #S13721208 , Image - 1
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13 Windfield Drive W Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13721208

Residential Freehold (Vacant Land)

$848000.0
A Rare Opportunity To Build Your Dream Home In One Of Shanty Bay's Most Exclusive Enclaves. Nestled On Coveted Windfields Drive at the end of a Cul-De
43 Photos
Last Updated : 16 Days ago
9992 Hwy 12 Highway, Simcoe, ON , MLS #S13513504 , Image - 1

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9992 Hwy 12 Highway Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13513504

Residential Freehold (Detached)

$699900.0
price drop iconPrice drop by 4.8%
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Check out this solid, older 5-bedroom, 3-bathroom home with a double car garage at 9992 Highway 12, just past Warminster and only minutes from Orillia
27 Photos
Last Updated : 16 Days ago
29 Oneida Avenue, Simcoe, ON , MLS #S14103244 , Image - 1

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29 Oneida Avenue Sugarbush, Oro-Medonte, Simcoe, ON MLS® S14103244

Residential Freehold (Detached)

$650000.0
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set on a spacious property of over half an acre and surrounded by mature trees and greenery, this peaceful s
27 Photos
Last Updated : 18 Days ago
90 Highland Drive, Simcoe, ON , MLS #S14104710 , Image - 1

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Unit-2094-2095, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14104710

Residential Condo & Other (Condo Apartment)

$414750.0
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Two living spaces. One unique opportunity in Horseshoe Valley. This spacious 2-bedroom, 2-bathroom condo offers a versatile two-residence configuratio
24 Photos
Last Updated : 19 Days ago
90 Highland Drive, Simcoe, ON , MLS #S13519786 , Image - 1

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Unit-2010/2011, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13519786

Residential Condo & Other (Condo Apartment)

$390000.0
price drop iconPrice drop by 6.0%
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Improved price! Live, work. play, profit! Welcome to resort style living at Horseshoe. This amazing unit in the Hansom building offers the rare abilit
3 Photos
Last Updated : 19 Days ago
90 Highland Drive, Simcoe, ON , MLS #S14029576 , Image - 1
Unit-2494/95, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14029576

Residential Condo & Other (Condo Apartment)

$559900.0
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to 90 Highland Dr, Units 2494 & 2495 - a truly unique opportunity in the sought-after Carriage Hills/Horseshoe Valley community of Oro-Medonte
47 Photos
Last Updated : 19 Days ago
39 Grandview Crescent, Simcoe, ON , MLS #S14107794 , Image - 1

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39 Grandview Crescent Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14107794

Residential Freehold (Detached)

$1495000.0
  • 4 +0 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this beautiful Lake Simcoe waterfront property, featuring a paved driveway, private hedge-lined front yard, two-car garage, and inviting fr
11 Photos
Last Updated : 20 Days ago
90 Highland Drive, Simcoe, ON , MLS #S13701426 , Image - 1

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Unit-2296-2297, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13701426

Residential Condo & Other (Condo Apartment)

$415000.0
price drop iconPrice drop by 9.0%
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Whether you're searching for a place to call home or a smart addition to your investment portfolio, this versatile property offers exceptional flexibi
14 Photos
Last Updated : 20 Days ago
90 Highland Drive, Simcoe, ON , MLS #S13739786 , Image - 1

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Unit-2252-2253, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13739786

Residential Condo & Other (Condo Apartment)

$449000.0
price drop iconPrice drop by 18.4%
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to 2252-53 90 Highland Dr in Carriage Hills, Horseshoe Valley-a fully furnished, turnkey four-season condo offering approximately 1,400 sq ft
37 Photos
Last Updated : 22 Days ago
40 Horseshoe Boulevard, Simcoe, ON , MLS #S14100118 , Image - 1

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Unit-Suite 206, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14100118

Residential Condo & Other (Condo Apartment)

$399900.0
  • 2 Beds
  • 2 Baths
  • 600-699 sq-ft
Welcome to Horseshoe Valley! Whether you're looking for a Year-Round Home or the Perfect Vacation Retreat, this inviting Condo in Copeland House offer
49 Photos
Last Updated : 22 Days ago
93 Moonstone Road E, Simcoe, ON , MLS #S14084226 , Image - 1

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93 Moonstone Road E Moonstone, Oro-Medonte, Simcoe, ON MLS® S14084226

Residential Freehold (Detached)

$1499000.0
  • 3 +2 Beds
  • 6 Baths
  • 3000-3500 sq-ft
Welcome Home To 93 Moonstone Road E in Oro-Medonte. This Fully Custom-Built Bungalow Offers Over 5,000 Sq. Ft. Of Finished Living Space On An Impressi
49 Photos
Last Updated : 23 Days ago
15 Private McKay Drive, Simcoe, ON , MLS #S13623426 , Image - 1

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15 Private McKay Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13623426

Residential Freehold (Detached)

$1485000.0
  • 5 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to the Highlander at Craighurst Crossing, where timeless modern farmhouse architecture meets exceptional craftsmanship in one of Oro-Medonte's
18 Photos
Last Updated : 23 Days ago
47 Moon Point Drive, Simcoe, ON , MLS #S13690360 , Image - 1

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47 Moon Point Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13690360

Residential Freehold (Detached)

$749000.0
  • 1 +1 Beds
  • 1 Baths
  • 700-1100 sq-ft
The Lot. The Location. The Lake. Prime Lake Simcoe Waterfront On A Sought-After Stretch Of Shoreline, Offering Over 100 Feet Of Pristine Frontage With
50 Photos
Last Updated : 23 Days ago
36 Highland Drive, Simcoe, ON , MLS #S14094654 , Image - 1

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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
20 Photos
Last Updated : 23 Days ago
6 Rosemarie Drive, Simcoe, ON , MLS #S14090756 , Image - 1

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6 Rosemarie Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14090756

Residential Freehold (Detached)

$769900.0
  • 3 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
QUICK CLOSING AVAILABLE! THE UPDATES ARE DONE, THE DECK IS CALLING & THE REC ROOM HAS SPACE FOR EVERYONE! Set on a generous 97 x 135 ft lot in a quiet
39 Photos
Last Updated : 23 Days ago
17 Bridle Path, Simcoe, ON , MLS #S14093684 , Image - 1

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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
10 Photos
Last Updated : 23 Days ago
2463 Dunns Line, Simcoe, ON , MLS #S13835938 , Image - 1

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2463 Dunns Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13835938

Residential Freehold (Vacant Land)

$799990.0
Build your dream home on this beautiful 25-acre property in desirable Oro-Medonte! Offering approximately 500 feet of road frontage, this property pro
26 Photos
Last Updated : 25 Days ago
90 Highland Drive, Simcoe, ON , MLS #S14089680 , Image - 1

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Unit-2286, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14089680

Residential Condo & Other (Condo Townhouse)

$538000.0
  • 2 Beds
  • 2 Baths
  • 1600-1799 sq-ft
Unit 2286 & 2287.... Welcome to 90 Highland Drive, an exceptional investment opportunity located in the picturesque location. This unique condo, compo
30 Photos
Last Updated : 26 Days ago
46 Pine Ridge Trail, Simcoe, ON , MLS #S13839158 , Image - 1

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

Residential Freehold (Detached)

$1185000.0
price drop iconPrice 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
50 Photos
Last Updated : 26 Days ago
15 Scottdale Drive, Simcoe, ON , MLS #S13866050 , Image - 1

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15 Scottdale Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13866050

Residential Freehold (Detached)

$1299000.0
  • 6 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Step inside this truly one-of-a-kind contemporary home in the sought-after Rugby Estates community, where a
34 Photos
Last Updated : 26 Days ago
90 Highland Drive, Simcoe, ON , MLS #S14087526 , Image - 1

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Unit-2264, 90 Highland Drive Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S14087526

Residential Condo & Other (Condo Apartment)

$389000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Experience the perfect blend of comfort, adventure, and investment potential with this fully upgraded, furnished property. Whether you're looking for
16 Photos
Last Updated : 26 Days ago
1897 10 Line N, Simcoe, ON , MLS #S13758294 , Image - 1

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1897 10 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13758294

Residential Freehold (Detached)

$779000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Experience peace and tranquility amidst nature on this stunning 2.6-acre property in the heart of Oro-Medont
37 Photos
Last Updated : 26 Days ago
5395 Line 8 N/A N, Simcoe, ON , MLS #S13754446 , Image - 1

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5395 Line 8 N/A N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13754446

Residential Freehold (Detached)

$1329900.0
  • 3 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Exquisite home set on over an acre, surrounded by hundreds of acres of tranquil forest and rolling farmland
32 Photos
Last Updated : 26 Days ago
40 HORSESHOE Boulevard, Simcoe, ON , MLS #S13736152 , Image - 1

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Unit-302, 40 HORSESHOE Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13736152

Residential Condo & Other (Condo Apartment)

$397900.0
price drop iconPrice drop by 0.3%
  • 1 +1 Beds
  • 2 Baths
  • 700-799 sq-ft
VACANT, PRICED TO SELL!**FOUR-SEASON GETAWAY WITH SKI HILL VIEWS, COVERED BALCONY, PARKING & LOCKER!** One-bedroom plus den layout in 756 sq. ft. with
50 Photos
Last Updated : 26 Days ago
11 Snowshoe Trail, Simcoe, ON , MLS #S13808550 , Image - 1

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11 Snowshoe Trail Moonstone, Oro-Medonte, Simcoe, ON MLS® S13808550

Residential Freehold (Detached)

$1075000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set on a spectacular half-acre treed lot, this property offers exceptional privacy and tranquility with towe
12 Photos
Last Updated : 26 Days ago
3 Valleycrest Drive, Simcoe, ON , MLS #S13800950 , Image - 1

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3 Valleycrest Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13800950

Residential Freehold (Vacant Land)

$475000.0
Top 5 Reasons You Will Love This Property: 1) Fully serviced building lot offering an exciting opportunity to bring your vision to life with essential
10 Photos
Last Updated : 26 Days ago
3 Owen Road, Simcoe, ON , MLS #S13745160 , Image - 1

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3 Owen Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13745160

Residential Freehold (Vacant Land)

$249900.0
Top 5 Reasons You Will Love This Property: 1) Build the home you've always wanted, this vacant parcel delivers the opportunity to start with a blank c
50 Photos
Last Updated : 26 Days ago
800 Mount St. Louis Road W, Simcoe, ON , MLS #S13744106 , Image - 1

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800 Mount St. Louis Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13744106

Residential Freehold (Detached)

$1149900.0
  • 3 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Nestled on nearly 4-acres of complete privacy surrounded by mature trees and picturesque views, delivering t
17 Photos
Last Updated : 26 Days ago
PT LT 40 Horseshoe Valley Road W, Simcoe, ON , MLS #S13573660 , Image - 1

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PT LT 40 Horseshoe Valley Road W Craighurst, Oro-Medonte, Simcoe, ON MLS® S13573660

Residential Freehold (Vacant Land)

$729900.0
Top 5 Reasons You Will Love This Property: 1) Extraordinary 27-acres parcel with nearly 2,000 feet of road frontage offering incredible potential, whe
39 Photos
Last Updated : 27 Days ago
16 Oneida Avenue, Simcoe, ON , MLS #S14080344 , Image - 1

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16 Oneida Avenue Sugarbush, Oro-Medonte, Simcoe, ON MLS® S14080344

Residential Freehold (Detached)

$998000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Built in 2011 and extensively renovated and remodeled in 2023, this turnkey home offers modern finishes, exceptional privacy, and a prime location in
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