Skip to main content
Sell Your Home
Shortlisted Properties
  • New Homes
  • For Sale
  • For Rent
Danger! Indicates a dangerous or potentially negative action.
Error

Maximum 4 project can be compared at one go.

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

Showing results 91 - 120 of 236
Last Updated: October 02, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
14 Photos
Last Updated : 9 Days ago
90 Highland Drive, Simcoe, ON , MLS #S13739786 , Image - 1
Image With Blur overlay

Like What you see?

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 90 Highland Dr in Carriage Hills, Horseshoe Valley-a fully furnished, turnkey four-season condo offering approximately 1,400 sq ft of flexi
26 Photos
Last Updated : 10 Days ago
90 Highland Drive, Simcoe, ON , MLS #S13812672 , Image - 1

Like What you see?

Unit-2072, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13812672

Residential Condo & Other (Condo Townhouse)

$530000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome to beautiful Highland Estates, one of Oro-Medonte's most desirable four-season communities! This fully furnished, move-in-ready two-bedroom, t
23 Photos
Last Updated : 10 Days ago
6 Maplehill Drive, Simcoe, ON , MLS #S13816172 , Image - 1

Like What you see?

6 Maplehill Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13816172

Residential Freehold (Detached)

$1149999.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
SPACE, PRIVACY, & SOPHISTICATED LIVING IN SIMCOE ESTATES! Tucked back from the road on an exceptional 190 x 255 ft lot, this executive bungalow offers
50 Photos
Last Updated : 10 Days ago
36 Highland Drive, Simcoe, ON , MLS #S13816496 , Image - 1

Like What you see?

36 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13816496

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
36 Photos
Last Updated : 10 Days ago
2 Thoroughbred Drive, Simcoe, ON , MLS #S13659548 , Image - 1

Like What you see?

2 Thoroughbred Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13659548

Residential Freehold (Detached)

$1275000.0
  • 3 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Motivated Sellers. Located in the heart of the highly sought-after Braestone community in Coldwater, where luxury living meets nature, family & connec
48 Photos
Last Updated : 10 Days ago
7 Georgian Grande Drive, Simcoe, ON , MLS #S13619582 , Image - 1

Like What you see?

7 Georgian Grande Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13619582

Residential Freehold (Detached)

$1398800.0
  • 2 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
** WATCH LISTING VIDEO ** Welcome to Braestone, where refined country living meets modern comfort. Set on a beautifully landscaped estate backing dire
50 Photos
Last Updated : 10 Days ago
114 11th Line S, Simcoe, ON , MLS #S13713916 , Image - 1

Like What you see?

114 11th Line S Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13713916

Residential Freehold (Detached)

$1165000.0
price drop iconPrice drop by 4.9%
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Spacious brick ranch bungalow on a 1.485 acre lot. This is a solid home with decent bones that is ready for your updating. Surrounded by mixed forest
43 Photos
Last Updated : 10 Days ago
9992 Hwy 12 Highway, Simcoe, ON , MLS #S13513504 , Image - 1

Like What you see?

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
49 Photos
Last Updated : 10 Days ago
7 ORSI Drive, Simcoe, ON , MLS #S13813466 , Image - 1

Like What you see?

7 ORSI Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13813466

Residential Freehold (Detached)

$1199900.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
It's not often you find this much space and privacy this close to Orillia. Tucked into the small community of Bass Lake Heights on a beautifully lands
6 Photos
Last Updated : 10 Days ago
1644 Ridge Road E, Simcoe, ON , MLS #S13750798 , Image - 1

Like What you see?

Unit-Vacant Land, 1644 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13750798

Residential Freehold (Vacant Land)

$249888.0
This Is A Rare Opportunity To Design A Custom Home That Reflects Your Vision And Lifestyle On A Beautiful 1.06-Acre Treed Building Lot In The Welcomin
32 Photos
Last Updated : 10 Days ago
1644 Ridge Road E, Simcoe, ON , MLS #S13750904 , Image - 1

Like What you see?

1644 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13750904

Residential Freehold (Detached)

$769888.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Imagine Coming Home To A Peaceful Country Setting Where Mature Trees Surround You, Neighbours Still Wave As They Pass By, And Life Moves At A More Com
30 Photos
Last Updated : 11 Days ago
17 Balantrae Drive, Simcoe, ON , MLS #S13802620 , Image - 1

Like What you see?

17 Balantrae Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13802620

Residential Freehold (MobileTrailer)

$249900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
EASY LIVING IN THIS LANDLEASE BUNGALOW IN FERGUSHILL ESTATES FEATURING TWO BEDROOMS, A BEAUTIFULLY UPGRADED BATHROOM, A SHED & ROOM TO ENJOY THE OUTDO
22 Photos
Last Updated : 11 Days ago
11 Woodland Crescent, Simcoe, ON , MLS #S12922472 , Image - 1

Like What you see?

11 Woodland Crescent Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12922472

Residential Freehold (Detached)

$1150000.0
price drop iconPrice drop by 19.0%
  • 3 +3 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to this exceptional, one-of-a-kind home in the highly sought-after community of Simcoe Estates. Situated on a private, mature lot spanning ove
14 Photos
Last Updated : 11 Days ago
5822 Line 8 N/A N, Simcoe, ON , MLS #S13810474 , Image - 1

Like What you see?

5822 Line 8 N/A N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13810474

Residential Freehold (Vacant Land)

$849900.0
Welcome to 5822 Line 8 N, a truly special 92-acre property in sought-after Oro-Medonte. Featuring mature forest, a picturesque spring-fed pond and end
43 Photos
Last Updated : 11 Days ago
224 Lakeshore Road E, Simcoe, ON , MLS #S13809130 , Image - 1

Like What you see?

224 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13809130

Residential Freehold (Detached)

$1199900.0
  • 2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Exceptional, low-maintenance home across from Lake Simcoe with beautiful deeded beach access. This quality-built property features high-end finishes t
21 Photos
Last Updated : 11 Days ago
16 Mazepa Place, Simcoe, ON , MLS #S13662042 , Image - 1

Like What you see?

16 Mazepa Place Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13662042

Residential Freehold (Detached)

$659900.0
price drop iconPrice drop by 2.9%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 16 Mazepa Place in Hawkstone! This charming 2-bedroom, 1-bathroom home offers approximately 1,000 sq. ft. of comfortable living space in a
50 Photos
Last Updated : 11 Days ago
11 Snowshoe Trail, Simcoe, ON , MLS #S13808550 , Image - 1

Like What you see?

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
8 Photos
Last Updated : 12 Days ago
71 Lakeshore Road E, Simcoe, ON , MLS #S13807160 , Image - 1

Like What you see?

71 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13807160

Residential Freehold (Detached)

$529000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
YOUR ORO-MEDONTE LAKE SIMCOE LIFESTYLE STARTS HERE! An opportunity to own a detached home just steps from Lake Simcoe at an incredibly accessible pric
42 Photos
Last Updated : 12 Days ago
24 Woodland Crescent, Simcoe, ON , MLS #S13649914 , Image - 1

Like What you see?

24 Woodland Crescent Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13649914

Residential Freehold (Detached)

$1248000.0
price drop iconPrice drop by 2.1%
  • 3 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Sprawling Bungalow over 5300 sq ft on 1.87 Acres, surrounded by forest and private. This unique home offers the potential for in law suite and/or the
42 Photos
Last Updated : 13 Days ago
13 Barnes Drive, Simcoe, ON , MLS #S13757966 , Image - 1

Like What you see?

13 Barnes Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13757966

Residential Freehold (Detached)

$1899900.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Discover refined estate living in an exclusive enclave of prestigious, municipally serviced homes, ideally situated approximately 45 minutes from the
21 Photos
Last Updated : 13 Days ago
45 Tamarack Drive, Simcoe, ON , MLS #S13745848 , Image - 1

Like What you see?

45 Tamarack Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13745848

Residential Freehold (Modular Home)

$550000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to effortless living in the highly sought-after, resident-run community of Big Cedar Estates. Offering nearly 1,400 square feet of comfortable
16 Photos
Last Updated : 14 Days ago
712 Line 9 Street S, Simcoe, ON , MLS #S13612934 , Image - 1

Like What you see?

712 Line 9 Street S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13612934

Residential Freehold (Detached)

$399900.0
price drop iconPrice drop by 10.7%
  • 1 Beds
  • 700-1100 sq-ft
Opportunity knocks! This over 1 acre lot has so much potential. Located just steps from Lake Simcoe, with easy access to HWY 11 and plenty of privacy,
41 Photos
Last Updated : 14 Days ago
1359 Old Barrie Road E, Simcoe, ON , MLS #S13710136 , Image - 1

Like What you see?

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
32 Photos
Last Updated : 14 Days ago
40 Horseshoe Boulevard, Simcoe, ON , MLS #S13801576 , Image - 1

Like What you see?

Unit-107, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13801576

Residential Condo & Other (Condo Apartment)

$431000.0
  • 1 +1 Beds
  • 2 Baths
  • 700-799 sq-ft
**RARE GROUND-FLOOR MOUNTAIN-VIEW SUITE AT HORSESHOE RESORT!** Imagine waking up to beautiful ski hill views, stepping directly onto your private gard
42 Photos
Last Updated : 14 Days ago
13 Georgina Drive S, Simcoe, ON , MLS #S13801200 , Image - 1

Like What you see?

13 Georgina Drive S Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13801200

Residential Freehold (Detached)

$3149000.0
  • 3 Beds
  • 4 Baths
  • 2000-2500 sq-ft
THE OPPORTUNITY IS NOW!!! 13 Georgina Drive is ready for its next chapter-THIS IS THE WATERFRONT YOU'VE BEEN WAITING FOR! Secure 120 FEET OF PRISTINE
12 Photos
Last Updated : 14 Days ago
3 Valleycrest Drive, Simcoe, ON , MLS #S13800950 , Image - 1

Like What you see?

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
48 Photos
Last Updated : 15 Days ago
1942 Ingram Road, Simcoe, ON , MLS #S13799822 , Image - 1

Like What you see?

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
49 Photos
Last Updated : 15 Days ago
15 Private McKay Drive, Simcoe, ON , MLS #S13623426 , Image - 1

Like What you see?

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
45 Photos
Last Updated : 15 Days ago
1415 15 16 Side Road E, Simcoe, ON , MLS #S13648774 , Image - 1

Like What you see?

1415 15 16 Side Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13648774

Residential Freehold (Detached)

$1098000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Elegance meets nature in this exceptional custom-built bungalow, nestled in the heart of Oro-Medonte. Situated on a premium 109' x 198' landscaped end
41 Photos
Last Updated : 15 Days ago
5222 6TH Line N, Simcoe, ON , MLS #S13795802 , Image - 1

Like What you see?

5222 6TH Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13795802

Residential Freehold (Detached)

$1170000.0
  • 2 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this exceptional custom-built Pacific Log Home, crafted by the Ontario Distributor of Pacific Log Homes and nestled on a spectacular privat
Shortlisted Properties
error icon
Error

Maximum 4 project can be compared at one go.

Related to your search
Tell us a Little about yourself!