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Detached Houses for Sale in Simcoe Under $5M - P34

Showing results 991 - 1020 of 3363
Last Updated: September 21, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
41 Photos
Last Updated : 6 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
35 Photos
Last Updated : 6 Days ago
9 Laidlaw Drive N, Simcoe, ON , MLS #S13527110 , Image - 1

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9 Laidlaw Drive N West Bayfield, Barrie, Simcoe, ON MLS® S13527110

Residential Freehold (Detached)

$669000.0
price drop iconPrice drop by 1.5%
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to the home that truly has the wow factor! From the moment you step inside, you'll appreciate the tasteful updates, bright open-concept design
33 Photos
Last Updated : 6 Days ago
139 Birkhall Place, Simcoe, ON , MLS #S13736144 , Image - 1

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139 Birkhall Place Innis-Shore, Barrie, Simcoe, ON MLS® S13736144

Residential Freehold (Detached)

$979000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
One owner, immaculately cared for 4 bedroom 4 bathroom all brick home. Corner lot for extra space, light and privacy. Grand entrance with sweeping sta
50 Photos
Last Updated : 6 Days ago
2384 Whetham Road, Simcoe, ON , MLS #S13723554 , Image - 1

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2384 Whetham Road Rural Springwater, Springwater, Simcoe, ON MLS® S13723554

Residential Freehold (Detached)

$874900.0
  • 5 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 2384 Whetham Road. Located on a quiet, dead end road just steps from Orr Lake, this property offers nearly half an acre of land and approxi
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
project size image
Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
44 Photos
Last Updated : 6 Days ago
1984 Wilson Street, Simcoe, ON , MLS #N13785008 , Image - 1

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1984 Wilson Street Alcona, Innisfil, Simcoe, ON MLS® N13785008

Residential Freehold (Detached)

$899900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Tucked against a peaceful treed backdrop, 1984 Wilson St offers the perfect combination of space, comfort and privacy for today's family. This invitin
33 Photos
Last Updated : 6 Days ago
32 Davis Street, Simcoe, ON , MLS #S13768884 , Image - 1

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32 Davis Street Collingwood, Simcoe, ON MLS® S13768884

Residential Freehold (Detached)

$829000.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to a beautifully refreshed, move-in-ready home in the desirable Creekside subdivision, minutes from downtown Collingwood, trails, parks, playg
37 Photos
Last Updated : 6 Days ago
1858 Woods Bay Road, Simcoe, ON , MLS #S13786078 , Image - 1

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1858 Woods Bay Road Rural Severn, Severn, Simcoe, ON MLS® S13786078

Residential Freehold (Detached)

$874999.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Beautifully designed four bedroom, three bathroom home where expansive water views take centre stage, with a
29 Photos
Last Updated : 6 Days ago
5512 3rd Line, Simcoe, ON , MLS #N13786040 , Image - 1

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5512 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13786040

Residential Freehold (Detached)

$2895000.0
  • 4 +1 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Just north of Schomberg and east of Tottenham sits this 50+ acre parcel that is ideal for those wanting to add land to their real estate portfolio or
49 Photos
Last Updated : 6 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
41 Photos
Last Updated : 6 Days ago
2 Alexandra Lane, Simcoe, ON , MLS #S13608282 , Image - 1

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2 Alexandra Lane Wasaga Beach, Simcoe, ON MLS® S13608282

Residential Freehold (Detached)

$999999.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to your Staycation Lifestyle. This property has an Outdoor Living Room. A Detached Luxury All-Season Private Wellness Pavillion with a Hydroth
46 Photos
Last Updated : 6 Days ago
2088 Wilkinson Street, Simcoe, ON , MLS #N13785872 , Image - 1

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2088 Wilkinson Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13785872

Residential Freehold (Detached)

$1599900.0
  • 3 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Exceptional 5.88-acre estate property presenting one of the largest parcels within this prestigious Innisfil
37 Photos
Last Updated : 6 Days ago
1441 Hendrie Road, Simcoe, ON , MLS #S13785852 , Image - 1

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1441 Hendrie Road Rural Springwater, Springwater, Simcoe, ON MLS® S13785852

Residential Freehold (Detached)

$1499000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Some properties earn the word resort. Ten private acres in Minesing, a salt-water inground pool, hot tub, pool house, bunkie, open-air cabana, a pond
47 Photos
Last Updated : 6 Days ago
9199 Highway 89 N/A, Simcoe, ON , MLS #N13484194 , Image - 1

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9199 Highway 89 N/A Rosemont, Adjala-Tosorontio, Simcoe, ON MLS® N13484194

Residential Freehold (Detached)

$774900.0
price drop iconPrice drop by 8.7%
  • 6 +1 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Looking for an excellent location to have a home business or simply enjoy a large family home & also have your parents live with you? The possibilitie
22 Photos
Last Updated : 6 Days ago
358 Livingstone Street W, Simcoe, ON , MLS #S13702612 , Image - 1

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358 Livingstone Street W Northwest, Barrie, Simcoe, ON MLS® S13702612

Residential Freehold (Detached)

$750000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
No neighbours behind! Welcome to 358 Livingstone St West. This 2600 sq ft three-bedroom 'Morra' built bungalow has been meticulously maintained by its
41 Photos
Last Updated : 6 Days ago
224 Margaret Street, Simcoe, ON , MLS #S13777658 , Image - 1

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224 Margaret Street Stayner, Clearview, Simcoe, ON MLS® S13777658

Residential Freehold (Detached)

$769900.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
OPEN HOUSE Saturday, September 19th 11:00 am - 1:00 pm Welcome to 224 Margaret Street in Stayner, where space, flexibility, and thoughtful updates com
46 Photos
Last Updated : 6 Days ago
118 Cauthers Crescent, Simcoe, ON , MLS #N13608742 , Image - 1

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118 Cauthers Crescent Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13608742

Residential Freehold (Detached)

$949999.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
A standout property on the block, this thoughtfully designed home offers premium features, smart functionality, and exceptional natural light througho
50 Photos
Last Updated : 6 Days ago
20 Mariposa Drive, Simcoe, ON , MLS #S13450248 , Image - 1

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20 Mariposa Drive Orillia, Simcoe, ON MLS® S13450248

Residential Freehold (Detached)

$749900.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Presenting 20 Mariposa Drive, a stunning family home in the highly sought-after north end neighbourhood of Orillia. This beautiful 2 storey home is pe
50 Photos
Last Updated : 6 Days ago
8128 Main Street, Simcoe, ON , MLS #N13753802 , Image - 1

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8128 Main Street Everett, Adjala-Tosorontio, Simcoe, ON MLS® N13753802

Residential Freehold (Detached)

$799999.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Nostalgia with modern touches welcomes you to this century home. A fully fenced yard on a 53 ft x 167 ft property invites you outside to find your zen
50 Photos
Last Updated : 6 Days ago
29 Gallagher Crescent, Simcoe, ON , MLS #S13785628 , Image - 1

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29 Gallagher Crescent Midhurst, Springwater, Simcoe, ON MLS® S13785628

Residential Freehold (Detached)

$1699999.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
29 Gallagher Crescent is located in one of Springwater most prestigious estate-home communities, offering a rare blend of luxury, privacy, and conveni
29 Photos
Last Updated : 6 Days ago
321 Park Street, Simcoe, ON , MLS #S13631232 , Image - 1

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321 Park Street Orillia, Simcoe, ON MLS® S13631232

Residential Freehold (Detached)

$625000.0
  • 3 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Brick bungalow in Orillia's sought-after North Ward - where mature trees, walkable streets, and everyday convenience meet. The fully fenced backyard i
50 Photos
Last Updated : 6 Days ago
1765 Flos Road 4 N/A W, Simcoe, ON , MLS #S13785594 , Image - 1

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1765 Flos Road 4 N/A W Rural Springwater, Springwater, Simcoe, ON MLS® S13785594

Residential Freehold (Detached)

$1150000.0
  • 3 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Escape to more than 9 acres backing onto hundreds of acres of Simcoe County Forest, whether you're exploring
41 Photos
Last Updated : 6 Days ago
7476 Ash Crescent, Simcoe, ON , MLS #S13718760 , Image - 1

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7476 Ash Crescent Rural Ramara, Ramara, Simcoe, ON MLS® S13718760

Residential Freehold (Detached)

$545000.0
price drop iconPrice drop by 3.5%
  • 5 Beds
  • 2 Baths
  • 700-1100 sq-ft
Black River waterfront living just minutes from Washago! This 5-bedroom, 2-bathroom home offers a great mix of waterfront living, space and year-roun
48 Photos
Last Updated : 6 Days ago
671 Simcoe Road, Simcoe, ON , MLS #N13658368 , Image - 1

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671 Simcoe Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13658368

Residential Freehold (Detached)

$789000.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Lovingly maintained bungalow with a separate basement entrance, offering exceptional versatility for families or multi-generational living. Ideally lo
50 Photos
Last Updated : 6 Days ago
3904 Concession 12 Sunnidale Side Road, Simcoe, ON , MLS #S13481018 , Image - 1

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3904 Concession 12 Sunnidale Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S13481018

Residential Freehold (Detached)

$1250000.0
  • 3 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to your private country retreat on 3.9 acres, ideally located across from the Simcoe County Forest. Offering over 3,000 sq. ft. of finished li
41 Photos
Last Updated : 6 Days ago
89 Connor Avenue, Simcoe, ON , MLS #S13785420 , Image - 1

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89 Connor Avenue Collingwood, Simcoe, ON MLS® S13785420

Residential Freehold (Detached)

$749000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
RENOVATED COMFORT IN DESIRABLE GEORGIAN MEADOWS, JUST MINUTES FROM PARKS, TRAILS, & OUTDOOR ADVENTURE! Welcome to the desirable Georgian Meadows commu
35 Photos
Last Updated : 6 Days ago
13 Abbey Crescent, Simcoe, ON , MLS #S13613926 , Image - 1

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13 Abbey Crescent Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13613926

Residential Freehold (Detached)

$1159000.0
price drop iconPrice drop by 3.3%
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to an exceptional open-concept family home offering 4 spacious bedrooms, 4 bathrooms, and premium finishes throughout. The heart of the home i
29 Photos
Last Updated : 6 Days ago
48 Plank Road, Simcoe, ON , MLS #N13669262 , Image - 1

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48 Plank Road Bond Head, Bradford West Gwillimbury, Simcoe, ON MLS® N13669262

Residential Freehold (Detached)

$1279900.0
price drop iconPrice drop by 5.2%
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Gorgeous Fully Upgraded, Fully Carpet-Free Detached Home in Bond Head, Simcoe County! Beautifully situated on a stunning ravine lot, this home offers
46 Photos
Last Updated : 6 Days ago
63 Adeline Avenue, Simcoe, ON , MLS #N13765590 , Image - 1

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63 Adeline Avenue Tottenham, New Tecumseth, Simcoe, ON MLS® N13765590

Residential Freehold (Detached)

$599999.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
GREAT BONES. HUGE LOT. SO MUCH POTENTIAL.If you've been waiting for a home you can make your own, this could be the one. Sitting on a large double lot
37 Photos
Last Updated : 6 Days ago
1475 River Road W, Simcoe, ON , MLS #S13785328 , Image - 1

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1475 River Road W Wasaga Beach, Simcoe, ON MLS® S13785328

Residential Freehold (Detached)

$599500.0
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 1475 River Road W, where this versatile raised bungalow offers a 2+2 bedroom layout, flexible living space, and an impressive 280-foot-deep
30 Photos
Last Updated : 6 Days ago
443 Elizabeth Street, Simcoe, ON , MLS #S13421260 , Image - 1

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443 Elizabeth Street Midland, Simcoe, ON MLS® S13421260

Residential Freehold (Detached)

$699900.0
price drop iconPrice drop by 12.5%
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
A UNIQUE, ONE OF A KIND HOME IN MIDLAND WITH ONE OF THE BEST SHOPS IN TOWN. Check out this classic red brick Midland home, which shows evident pride o
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