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5 Bedroom Houses for Sale in Simcoe Under $1M - P2

Showing results 31 - 60 of 76
Last Updated: September 20, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
48 Photos
Last Updated : 11 Days ago
43 Davies Crescent, Simcoe, ON , MLS #S13763168 , Image - 1
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43 Davies Crescent Grove East, Barrie, Simcoe, ON MLS® S13763168

Residential Freehold (Detached)

$726999.0
  • 5 +2 Beds
  • 4 Baths
  • 700-1100 sq-ft
Beautifully renovated home on a large lot in Barrie's sought-after East End! Features an open-concept layout with luxury vinyl plank flooring througho
50 Photos
Last Updated : 11 Days ago
32 Bridlewood Crescent, Simcoe, ON , MLS #S13508386 , Image - 1

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32 Bridlewood Crescent Wasaga Beach, Simcoe, ON MLS® S13508386

Residential Freehold (Detached)

$839900.0
price drop iconPrice drop by 5.6%
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Located in the sought-after Sunward Estates community and just two doors from a scenic walking trail leading to Allenwood Beach (approx. 12-minute wal
50 Photos
Last Updated : 12 Days ago
83 Bearberry Road, Simcoe, ON , MLS #S13756898 , Image - 1

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83 Bearberry Road Midhurst, Springwater, Simcoe, ON MLS® S13756898

Residential Freehold (Detached)

$839990.0
  • 5 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to this luxurious Countrywide 2,814 sq. ft. five-bedroom home, beautifully upgraded with approximately $150,000 in premium finishes. This exce
20 Photos
Last Updated : 12 Days ago
3929 WOOD Avenue, Simcoe, ON , MLS #S13756520 , Image - 1

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3929 WOOD Avenue West Shore, Severn, Simcoe, ON MLS® S13756520

Residential Freehold (Duplex)

$775000.0
  • 5 +0 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Steps to the lake, this beautiful purpose built duplex has partial ownership of a waterfront park & beach with communal dock access on Lake Couchichin
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
16 Photos
Last Updated : 12 Days ago
3114 Emperor Drive, Simcoe, ON , MLS #S13752824 , Image - 1

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3114 Emperor Drive Orillia, Simcoe, ON MLS® S13752824

Residential Freehold (Duplex)

$774999.0
  • 5 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Outstanding investment opportunity in the highly desirable Westridge community, offering a purpose-built ren
24 Photos
Last Updated : 12 Days ago
3118 Emperor Drive, Simcoe, ON , MLS #S13752688 , Image - 1

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3118 Emperor Drive Orillia, Simcoe, ON MLS® S13752688

Residential Freehold (Duplex)

$774999.0
  • 5 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Nestled in the highly desirable Westridge neighbourhood, this purpose-built rental property enjoys a prime l
36 Photos
Last Updated : 12 Days ago
259 Centre Street, Simcoe, ON , MLS #S13618232 , Image - 1

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259 Centre Street Stayner, Clearview, Simcoe, ON MLS® S13618232

Residential Freehold (Detached)

$999000.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to 259 Centre Street, an exceptional executive home built in 2023, offering modern design, premium upgrades, and outstanding flexibility for t
40 Photos
Last Updated : 14 Days ago
1 Walker Boulevard, Simcoe, ON , MLS #N13602804 , Image - 1

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1 Walker Boulevard Alliston, New Tecumseth, Simcoe, ON MLS® N13602804

Residential Freehold (Detached)

$899900.0
price drop iconPrice drop by 10.0%
  • 5 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
This Beautifully upgraded & immaculately maintained over 3200 Sq Ft Executive Home In the highly Sought-After Alliston Community offers A Perfect Blen
28 Photos
Last Updated : 16 Days ago
76 Wellington Street, Simcoe, ON , MLS #N13746866 , Image - 1

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76 Wellington Street Alliston, New Tecumseth, Simcoe, ON MLS® N13746866

Residential Freehold (Triplex)

$859000.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Fully renovated legal triplex in the heart of Alliston - a turnkey, separately metered income property built for the hands-off investor. Three self-co
1 Photos
Last Updated : 16 Days ago
35 Sassafras Road, Simcoe, ON
35 Sassafras Road Midhurst, Springwater, Simcoe, ON MLS® S13744476

Residential Freehold (Detached)

$899991.0
  • 5 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to this beautifully appointed brand new 2800 sq. ft. home built by award winning Brookfield Residential located in the sought after Midhurst V
31 Photos
Last Updated : 16 Days ago
121 Allegra Drive, Simcoe, ON , MLS #S13479080 , Image - 1

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121 Allegra Drive Wasaga Beach, Simcoe, ON MLS® S13479080

Residential Freehold (Detached)

$999000.0
  • 5 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Fresh air, quiet streets and that rare ability to feel away from it all while still being close to everything. This is the reason people move to Wasag
17 Photos
Last Updated : 18 Days ago
199 Nottawasaga Street, Simcoe, ON , MLS #S13739074 , Image - 1

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199 Nottawasaga Street Orillia, Simcoe, ON MLS® S13739074

Residential Freehold (Triplex)

$950000.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Turnkey Investment or Live & Rent! Premium Legal Triplex with Garden Suite PotentialMaximize your real estate portfolio with this exceptionally well-m
49 Photos
Last Updated : 19 Days ago
29 TECUMSETH Street, Simcoe, ON , MLS #S13622146 , Image - 1

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29 TECUMSETH Street Orillia, Simcoe, ON MLS® S13622146

Residential Freehold (Detached)

$849000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Welcome to 29 Tecumseth Street in Orillia, a distinctive 2 1/2-storey century home where history meets modern updates. Originally built in 1900 just a
36 Photos
Last Updated : 19 Days ago
208 Lamont Court, Simcoe, ON , MLS #S13732348 , Image - 1

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208 Lamont Court Stayner, Clearview, Simcoe, ON MLS® S13732348

Residential Freehold (Detached)

$819000.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
This is where space, comfort, and lifestyle come together. Welcome to 208 Lamont Court in Stayner, a beautifully updated raised bungalow set on an ove
17 Photos
Last Updated : 19 Days ago
2670 SOUTH SPARROW LAKE Road, Simcoe, ON , MLS #S13609264 , Image - 1

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2670 SOUTH SPARROW LAKE Road Rural Severn, Severn, Simcoe, ON MLS® S13609264

Residential Freehold (Detached)

$999000.0
price drop iconPrice drop by 9.2%
  • 5 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
This is 57 Acres of Private Paradise! Enjoy approximately 57 acres of picturesque countryside with a private driveway leading to two homes on the prop
29 Photos
Last Updated : 20 Days ago
238 Sixth Street, Simcoe, ON , MLS #S13702204 , Image - 1

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238 Sixth Street Midland, Simcoe, ON MLS® S13702204

Residential Freehold (Detached)

$649900.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Step into the timeless charm of this beautifully maintained century home, offering the perfect blend of character, comfort, and versatility. Lovingly
40 Photos
Last Updated : 21 Days ago
229 Datas Drive E, Simcoe, ON , MLS #S13101416 , Image - 1

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229 Datas Drive E Stayner, Clearview, Simcoe, ON MLS® S13101416

Residential Freehold (Detached)

$649000.0
price drop iconPrice drop by 7.3%
  • 5 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Quality brick bungalow in a prime Stayner location. Welcome to 229 Datas Drive East, a solid and well-cared-for home built in 1985 by the respected Wo
42 Photos
Last Updated : 22 Days ago
112 Farlain Lake Road E, Simcoe, ON , MLS #S13644352 , Image - 1

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112 Farlain Lake Road E Rural Tiny, Tiny, Simcoe, ON MLS® S13644352

Residential Freehold (Detached)

$800000.0
  • 5 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Three-season cottage offering a unique two-structure setup with plenty of room for family and guests, featur
50 Photos
Last Updated : 24 Days ago
298 Seventh Street, Simcoe, ON , MLS #S13719098 , Image - 1

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298 Seventh Street Midland, Simcoe, ON MLS® S13719098

Residential Freehold (Detached)

$889900.0
  • 5 +1 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to this spacious and versatile 5+1 bedroom, 4+1 bathroom home in Midland, offering an exceptional blend of space, functionality, and flexibili
20 Photos
Last Updated : 24 Days ago
874 Cedar Point Road, Simcoe, ON , MLS #S13717464 , Image - 1

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874 Cedar Point Road Rural Tiny, Tiny, Simcoe, ON MLS® S13717464

Residential Freehold (Detached)

$524000.0
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Brimming with Character and Country Charm! This timeless two-storey home offers the perfect combination of space, warmth, and opportunity. Featuring 5
48 Photos
Last Updated : 25 Days ago
76 CALYPSO Avenue, Simcoe, ON , MLS #S13492752 , Image - 1

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76 CALYPSO Avenue Midhurst, Springwater, Simcoe, ON MLS® S13492752

Residential Freehold (Detached)

$999900.0
price drop iconPrice drop by 6.1%
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome To 76 Calypso Ave In Sought-After Midhurst! This Exceptional 5 Bedrooms, 4 Bathroom Detached 2-Storey Home Sits On A Premium Ravine Lot And Of
22 Photos
Last Updated : 25 Days ago
246 Mary Street, Simcoe, ON , MLS #S13652024 , Image - 1

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246 Mary Street Orillia, Simcoe, ON MLS® S13652024

Residential Freehold (Detached)

$499900.0
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
VERSATILE 2-STOREY HOME WITH TWO SELF-CONTAINED LIVING SPACES ON AN EXTRA-DEEP LOT IN THE HEART OF ORILLIA! Rarely offered and full of opportunity, th
43 Photos
Last Updated : 30 Days ago
122 Thicketwood Avenue, Simcoe, ON , MLS #S13687398 , Image - 1

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122 Thicketwood Avenue Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13687398

Residential Freehold (Detached)

$919000.0
  • 5 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to Everwell South Barrie, an exclusive community on the city's southern edge. This luxury 2,943 sq. ft. detached home by Sorbara is move-in re
46 Photos
Last Updated : 32 Days ago
1108 Trombley Street, Simcoe, ON , MLS #N13621610 , Image - 1

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1108 Trombley Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13621610

Residential Freehold (Detached)

$839000.0
price drop iconPrice drop by 1.2%
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 1108 Trombley Street, a unique lakeside property in the charming hamlet of Belle Ewart, just steps from Lake Simcoe and approximately 45 mi
32 Photos
Last Updated : 34 Days ago
9775 Beachwood Road, Simcoe, ON , MLS #S13684034 , Image - 1

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9775 Beachwood Road Collingwood, Simcoe, ON MLS® S13684034

Residential Freehold (Detached)

$499900.0
  • 5 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 9775 Beachwood Rd - a rare opportunity combining four-season living, an impressive 60' x 250' mature-treed lot and exciting long-term poten
50 Photos
Last Updated : 34 Days ago
103 Mulcaster Street, Simcoe, ON , MLS #S13110124 , Image - 1

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103 Mulcaster Street Codrington, Barrie, Simcoe, ON MLS® S13110124

Residential Freehold (Duplex)

$575000.0
price drop iconPrice drop by 4.0%
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
103 Mulcaster Street is a legally registered duplex ideally situated in the heart of downtown Barrie, just steps from Kempenfelt Bay, restaurants, cit
50 Photos
Last Updated : 36 Days ago
537 Ste Marie Street, Simcoe, ON , MLS #S13127624 , Image - 1

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537 Ste Marie Street Collingwood, Simcoe, ON MLS® S13127624

Residential Freehold (Detached)

$699000.0
price drop iconPrice drop by 17.7%
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
UNIQUE OPPORTUNITY to purchase a delightful 3 Bedroom Victorian heritage property with wrap around porch and ample parking in an excellent location an
24 Photos
Last Updated : 37 Days ago
6331 26 Highway, Simcoe, ON , MLS #S13676024 , Image - 1

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6331 26 Highway Rural Clearview, Clearview, Simcoe, ON MLS® S13676024

Residential Freehold (Detached)

$799900.0
  • 5 Beds
  • 1 Baths
  • 2000-2500 sq-ft
8.65 Acres With Room To Grow Your Investment! Set across expansive, cleared and level agricultural land along Highway 26, this century property offers
49 Photos
Last Updated : 39 Days ago
61 Dyer Drive, Simcoe, ON , MLS #S13652550 , Image - 1

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61 Dyer Drive Wasaga Beach, Simcoe, ON MLS® S13652550

Residential Freehold (Detached)

$732500.0
  • 5 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 61 Dyer Drive, a beautifully maintained family home offering over 2,500 sq. ft. of finished living space in one of Wasaga Beach's most desi
39 Photos
Last Updated : 39 Days ago
45 Ivy Lane, Simcoe, ON , MLS #S13595768 , Image - 1

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45 Ivy Lane Orillia, Simcoe, ON MLS® S13595768

Residential Freehold (Detached)

$998000.0
  • 5 Beds
  • 5 Baths
  • 1500-2000 sq-ft
233 ft of Waterfront double lot on Grape Island! Join the shipping container lifestyle revolution! Original and updated Lake Simcoe waterfront cottage
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