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Houses for Sale in Oro-Medonte ON Under $2 Million - P4

Showing results 91 - 120 of 224
Last Updated: September 26, 2026
  • 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 : 11 Days ago
8 Myrtle Avenue, Simcoe, ON , MLS #S13788312 , Image - 1
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8 Myrtle Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13788312

Residential Freehold (Detached)

$469900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Fully Renovated From Top To Bottom Over The Last 5 Years! Completely Turn-Key, Cozy Bungalow Situated On Large 50 x 110 Ft Lot With No Neighbours Behi
29 Photos
Last Updated : 11 Days ago
4201 Line 8 Line N, Simcoe, ON , MLS #S13690292 , Image - 1

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4201 Line 8 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13690292

Residential Freehold (Farm)

$1465000.0
  • 4 +0 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Country charm and wide-open space come together on this beautiful 47-acre property, complete with great fields, a river stream, and a stunning creek -
14 Photos
Last Updated : 11 Days ago
33 Fifth Line S, Simcoe, ON , MLS #S13467206 , Image - 1

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33 Fifth Line S Guthrie, Oro-Medonte, Simcoe, ON MLS® S13467206

Residential Freehold (Detached)

$649900.0
price drop iconPrice drop by 18.3%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Move right in to this well planned bungalow, surrounded by a cottage feel but with school and highway access close by. The bright living room is read
32 Photos
Last Updated : 11 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
41 Photos
Last Updated : 11 Days ago
7 Pine Spring N/A, Simcoe, ON , MLS #S13786340 , Image - 1

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7 Pine Spring N/A Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13786340

Residential Freehold (Detached)

$749900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Calling outdoor enthusiasts! Mountain biking trails, hiking, snowshoeing, snowmobiling, skiing and golf right at your door step with this spectacular
49 Photos
Last Updated : 11 Days ago
1772 10 Line N, Simcoe, ON , MLS #S13765138 , Image - 1

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1772 10 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13765138

Residential Freehold (Detached)

$1899000.0
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Privately set on 9+ wooded acres behind a gated entrance, this exceptional Oro-Medonte estate offers a rare combination of refined country living, imp
Open House : Sat Sep 26, 11:00 AM to 01:00 PM
18 Photos
Last Updated : 11 Days ago
1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S13480864 , Image - 1

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Unit-108, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13480864

Residential Condo & Other (Condo Townhouse)

$319999.0
  • 1 Beds
  • 1 Baths
  • 500-599 sq-ft
Welcome to easy living in the heart of Horseshoe Valley. This main floor walk-in unit with no stairs offers an ideal opportunity for retirees, first-t
50 Photos
Last Updated : 12 Days ago
1016 Lakeshore Road E, Simcoe, ON , MLS #S13766760 , Image - 1

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1016 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13766760

Residential Freehold (Detached)

$1499000.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
CUSTOM LUXURY BUNGALOW MEETS LAKESIDE LIVING - NEARLY 4,500 FINISHED SQ. FT., DESIGNER FINISHES, IN-LAW POTENTIAL & OVER HALF AN ACRE, STEPS FROM LAKE
12 Photos
Last Updated : 12 Days ago
108 Lakeshore Road E, Simcoe, ON , MLS #S13781656 , Image - 1

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108 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13781656

Residential Freehold (Vacant Land)

$225000.0
Build your dream home across from the sparkling shores of Lake Simcoe! Welcome to 108 Lakeshore Road East in Oro-Medonte - a prime quarter-acre buildi
50 Photos
Last Updated : 12 Days ago
116 Mill Pond Side Road, Simcoe, ON , MLS #S13780894 , Image - 1

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116 Mill Pond Side Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13780894

Residential Freehold (Detached)

$1899000.0
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to this nature lover's retreat! If you have been searching for a large acreage property in Oro Medonte, look no further. This private and secl
46 Photos
Last Updated : 12 Days ago
1174 15 Line N, Simcoe, ON , MLS #S13151618 , Image - 1

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1174 15 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13151618

Residential Freehold (Detached)

$1199900.0
price drop iconPrice drop by 17.2%
  • 5 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Rare opportunity to own a west facing, waterfront home on sought-after Bass Lake. Situated on a generous lot with 40 ft of sandy shoreline, this prope
40 Photos
Last Updated : 12 Days ago
2330 Lakeshore Road E, Simcoe, ON , MLS #S13608066 , Image - 1

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2330 Lakeshore Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13608066

Residential Freehold (Detached)

$775000.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Charming Renovated Bungalow in Beautiful Oro-Medonte. Welcome to this beautifully renovated 2+1 bedroom bungalow nestled in the heart of Simcoe County
42 Photos
Last Updated : 12 Days ago
21 Ruby Ridge, Simcoe, ON , MLS #S13746620 , Image - 1

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21 Ruby Ridge Sugarbush, Oro-Medonte, Simcoe, ON MLS® S13746620

Residential Freehold (Detached)

$1249000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Pride of ownership in this immaculate newer raised bungalow with walk out. Oversized lot on 3/4 acres with no back neighbour and extended side yard wi
39 Photos
Last Updated : 13 Days ago
57 Highland Drive, Simcoe, ON , MLS #S13742900 , Image - 1

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57 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13742900

Residential Freehold (Detached)

$1099999.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to refined four-season living in the heart of Horseshoe Valley-an emerging Blue Zone inspired community where an active, healthy lifestyle com
30 Photos
Last Updated : 13 Days ago
13 Alpine Way, Simcoe, ON , MLS #S13742930 , Image - 1

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13 Alpine Way Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13742930

Residential Freehold (Detached)

$1250000.0
  • 1 +3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Set in the heart of Horseshoe Valley, within an exclusive enclave of fine homes, this exceptional property offers a lifestyle many consider a true Blu
48 Photos
Last Updated : 13 Days ago
7 Clydesdale Court, Simcoe, ON , MLS #S13759756 , Image - 1

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7 Clydesdale Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13759756

Residential Freehold (Detached)

$1625000.0
  • 3 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Discover Braestone, an exceptional community where neighbours know each other's names and spontaneous gatherings happen often and feel effortless. Su
44 Photos
Last Updated : 14 Days ago
126 Brambel Road, Simcoe, ON , MLS #S13536646 , Image - 1

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126 Brambel Road Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13536646

Residential Freehold (Detached)

$1500000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Nestled at the very end of a quiet, prestigious dead end street, this private woodland retreat on Brambel Road offers the best of both worlds: a seren
47 Photos
Last Updated : 15 Days ago
39 Grandview Crescent, Simcoe, ON , MLS #S13691918 , Image - 1

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39 Grandview Crescent Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13691918

Residential Freehold (Detached)

$1549999.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
104 FEET OF PRIVATE LAKE SIMCOE FRONTAGE! Set along a quiet stretch of shoreline in one of Oro's most sought-after lakefront communities, this is the
50 Photos
Last Updated : 15 Days ago
24 Brambel Road, Simcoe, ON , MLS #S13731472 , Image - 1

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24 Brambel Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13731472

Residential Freehold (Detached)

$1049000.0
price drop iconPrice drop by 6.3%
  • 4 +0 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Nestled among mature trees and beautifully landscaped grounds on a private waterfront road with shoreline access to Lake Simcoe, this custom-built hom
50 Photos
Last Updated : 16 Days ago
4 Cheslock Crescent, Simcoe, ON , MLS #S13759344 , Image - 1

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4 Cheslock Crescent Warminster, Oro-Medonte, Simcoe, ON MLS® S13759344

Residential Freehold (Detached)

$1525000.0
  • 4 +2 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Impressive six bedroom two-storey home set on nearly an acre of beautifully landscaped property in the growi
40 Photos
Last Updated : 16 Days ago
9 Bridle Path, Simcoe, ON , MLS #S13757332 , Image - 1

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9 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13757332

Residential Freehold (Detached)

$1399900.0
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
This home offers the rare combination of serene country living and exceptional convenience, nestled on a picturesque, tree-lined lot just minutes from
50 Photos
Last Updated : 16 Days ago
4 Diamond Valley Drive, Simcoe, ON , MLS #S13467394 , Image - 1

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4 Diamond Valley Drive Sugarbush, Oro-Medonte, Simcoe, ON MLS® S13467394

Residential Freehold (Detached)

$1190000.0
price drop iconPrice drop by 7.8%
  • 3 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set against a stunning forested landscape, this exclusive Maplewood Estates model home in Sugar Bush offers
32 Photos
Last Updated : 16 Days ago
23 Owen Road, Simcoe, ON , MLS #S13744782 , Image - 1

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23 Owen Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13744782

Residential Freehold (Detached)

$549900.0
  • 2 Beds
  • 1 Baths
  • 1100-1500 sq-ft
OVERVIEW Well-maintained bungalow located in a desirable Simcoeside Community in Oro-Medonte, just minutes from Barrie and Orillia. Enjoy convenient a
24 Photos
Last Updated : 16 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)

$403000.0
price drop iconPrice drop by 2.9%
  • 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
48 Photos
Last Updated : 16 Days ago
465 Ridge Road E, Simcoe, ON , MLS #S13764294 , Image - 1

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465 Ridge Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13764294

Residential Freehold (Rural Residential)

$1999000.0
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Experience the ultimate equestrian lifestyle in the heart of desirable Oro-Medonte. This stunning 20+ acre estate is perfectly positioned for the acti
28 Photos
Last Updated : 17 Days ago
49 Red Oak Crescent, Simcoe, ON , MLS #S13607350 , Image - 1

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49 Red Oak Crescent Shanty Bay, Oro-Medonte, Simcoe, ON MLS® S13607350

Residential Freehold (Detached)

$1349000.0
price drop iconPrice drop by 9.3%
  • 4 +4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Rarely offered in the highly sought-after Shanty Bay community, this exceptional residence at 49 Red Oak Crescent presents a rare opportunity to own a
35 Photos
Last Updated : 17 Days ago
1998 Old Barrie Road E, Simcoe, ON , MLS #S13544340 , Image - 1

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1998 Old Barrie Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13544340

Residential Freehold (Detached)

$499999.0
price drop iconPrice drop by 23.0%
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Renovated Century home on approximately .6 acre lot (approx 150 FT x 175 Ft) . Kitchen has 2 islands and lots of natural light. There are three bedroo
20 Photos
Last Updated : 17 Days ago
6 Rosemarie Drive, Simcoe, ON , MLS #S13748934 , Image - 1

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6 Rosemarie Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13748934

Residential Freehold (Detached)

$799900.0
  • 3 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
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 neighbourhood near Lake
49 Photos
Last Updated : 17 Days ago
14 Conder Drive, Simcoe, ON , MLS #S12768592 , Image - 1

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14 Conder Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12768592

Residential Freehold (Detached)

$660000.0
price drop iconPrice drop by 14.8%
  • 4 +0 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this lovely renovated home on a huge lot not far from either Orillia or Coldwater! The foyer welcomes you into this open concept home with
42 Photos
Last Updated : 17 Days ago
10 Green Mountain Court, Simcoe, ON , MLS #S13746216 , Image - 1

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10 Green Mountain Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13746216

Residential Freehold (Detached)

$1299900.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set on just over one acre along a quiet dead-end road in the prestigious Simcoe Estates community of Oro-Med
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