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

Showing results 31 - 60 of 217
Last Updated: September 21, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
48 Photos
Last Updated : 3 Days ago
1659 Emberton Way, Simcoe, ON , MLS #N13801752 , Image - 1
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1659 Emberton Way Rural Innisfil, Innisfil, Simcoe, ON MLS® N13801752

Residential Freehold (Detached)

$1199000.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Experience Luxury Living at Belle Aire Shores! Just moments from the shimmering shores of Lake Simcoe, this magnificent 3,600+ sq. ft. residence is a
8 Photos
Last Updated : 3 Days ago
1024 Ewart Street, Simcoe, ON , MLS #N13053244 , Image - 1

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1024 Ewart Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13053244

Residential Freehold (Store W Apartment/Office)

$799999.0
  • 5 +2 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Discover an exceptional and versatile investment opportunity just steps from Lake Simcoe. This unique mixed-use property offers multiple income-genera
38 Photos
Last Updated : 3 Days ago
15 Calypso Avenue, Simcoe, ON , MLS #S13736802 , Image - 1

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15 Calypso Avenue Midhurst, Springwater, Simcoe, ON MLS® S13736802

Residential Freehold (Detached)

$999900.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to this impressive 3,723 sq. ft. Hawkstone design, built by award-winning Geranium in the sought-after Midhurst Valley community of Springwate
44 Photos
Last Updated : 3 Days ago
7665 36/37 NOTTAWASAGA Side Road W, Simcoe, ON , MLS #S13496572 , Image - 1

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7665 36/37 NOTTAWASAGA Side Road W Nottawa, Clearview, Simcoe, ON MLS® S13496572

Residential Freehold (Detached)

$2999000.0
price drop iconPrice drop by 14.3%
  • 5 Beds
  • 3 Baths
  • 5000 + sq-ft
Prepare to be captivated. Set on 18 private acres overlooking the breathtaking Pretty River, this extraordinary custom-built log home is a masterpiece
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
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Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
20 Photos
Last Updated : 4 Days ago
26 Birchwood Lane, Simcoe, ON , MLS #N13717762 , Image - 1

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26 Birchwood Lane Rural Essa, Essa, Simcoe, ON MLS® N13717762

Residential Freehold (Detached)

$1748900.0
price drop iconPrice drop by 12.6%
  • 5 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Luxury Estate Living on a Premium 2.02-Acre Lot! This spectacular never-lived in detached home offers 5,000+sq.ft of luxurious living space, a 3-car
40 Photos
Last Updated : 4 Days ago
105 McKenzie Way, Simcoe, ON , MLS #N13700766 , Image - 1

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105 McKenzie Way Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13700766

Residential Freehold (Detached)

$1377000.0
  • 5 +1 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Welcome To A Beautiful & Modern 5 Bedroom Home In a Family Friendly Area With a Bright Open Concept Layout & Custom Finishings Throughout The House. A
49 Photos
Last Updated : 4 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
38 Photos
Last Updated : 4 Days ago
7 Stewart Crescent, Simcoe, ON , MLS #N13719860 , Image - 1

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7 Stewart Crescent Thornton, Essa, Simcoe, ON MLS® N13719860

Residential Freehold (Detached)

$1549000.0
price drop iconPrice drop by 3.1%
  • 5 +1 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Extremely Rare Offering Prestigious Thornton Estates. Welcome to this exceptional family estate nestled in the highly sought-after Thornton Estates Co
37 Photos
Last Updated : 4 Days ago
3930 Yonge Street, Simcoe, ON , MLS #N13685342 , Image - 1

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3930 Yonge Street Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13685342

Residential Freehold (Rural Residential)

$2599888.0
price drop iconPrice drop by 5.5%
  • 5 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Welcome to 3930 Yonge Street in Bradford. This Unique Property is 6.28 Acres and Zoned (A*29)which Offers Both Residential and Commercial Uses. Presen
50 Photos
Last Updated : 4 Days ago
3219 Hampshire Mills Line, Simcoe, ON , MLS #S13786308 , Image - 1

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3219 Hampshire Mills Line Rural Severn, Severn, Simcoe, ON MLS® S13786308

Residential Freehold (Detached)

$2600000.0
  • 5 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Set on 1.4 acres, this exceptional five-bedroom estate offers over 6,400 sq. ft. of finished living space, thoughtfully expanded and renovated with a
32 Photos
Last Updated : 4 Days ago
1144 Wickham Road, Simcoe, ON , MLS #N13508276 , Image - 1

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1144 Wickham Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13508276

Residential Freehold (Detached)

$1049000.0
price drop iconPrice drop by 4.5%
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Light bright and spacious this rare 5 bedroom model in Fernbrook Homes Bell Aire Shores community is well worth viewing. 3600 sq ft of living area mea
49 Photos
Last Updated : 4 Days ago
190 Strachan Trail, Simcoe, ON , MLS #N13741360 , Image - 1

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190 Strachan Trail Beeton, New Tecumseth, Simcoe, ON MLS® N13741360

Residential Freehold (Detached)

$1349900.0
  • 5 +2 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Welcome home to this stunning, 3,800 sq. ft. executive residence in the growing community of Beeton. Backing onto serene greenspace with coveted south
48 Photos
Last Updated : 4 Days ago
8352 Main Lisle Street, Simcoe, ON , MLS #N13795436 , Image - 1

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8352 Main Lisle Street Lisle, Adjala-Tosorontio, Simcoe, ON MLS® N13795436

Residential Freehold (Detached)

$999900.0
  • 5 +6 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Investor/Extended Family Opportunity on an oversized Lot! Situated on an expansive 82 x 602 ft lot backing onto a serene forest, this private propert
41 Photos
Last Updated : 4 Days ago
2997 Stone Ridge Boulevard, Simcoe, ON , MLS #S13559916 , Image - 1

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2997 Stone Ridge Boulevard Orillia, Simcoe, ON MLS® S13559916

Residential Freehold (Detached)

$799999.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Whether you're searching for a spacious single-family home, a true multigenerational property with a private in-law suite, or an investment opportunit
46 Photos
Last Updated : 5 Days ago
2944 County Road 50 Road, Simcoe, ON , MLS #N13794682 , Image - 1

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2944 County Road 50 Road Loretto, Adjala-Tosorontio, Simcoe, ON MLS® N13794682

Residential Freehold (Detached)

$1150000.0
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Welcome to this beautifully renovated country home with 5 bedrooms and 2 bathrooms, where modern updates meet spacious living and a peaceful setting.
50 Photos
Last Updated : 5 Days ago
4082 Graham Road, Simcoe, ON , MLS #S13729646 , Image - 1

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4082 Graham Road Rural Severn, Severn, Simcoe, ON MLS® S13729646

Residential Freehold (Detached)

$1875000.0
  • 5 Beds
  • 2 Baths
  • 3000-3500 sq-ft
TEA LAKE - TURN KEY AND READY TO ENJOY Imagine, Arrive, unpack and start enjoying Cottage Life. Just Bring your Groceries! 236 ft of Beautiful SOUTHER
32 Photos
Last Updated : 5 Days ago
14 Imperial Crown Lane, Simcoe, ON , MLS #S13554762 , Image - 1

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14 Imperial Crown Lane Innis-Shore, Barrie, Simcoe, ON MLS® S13554762

Residential Freehold (Detached)

$895000.0
price drop iconPrice drop by 3.2%
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Beautifully maintained and upgraded! Situated in this exclusive Royal Parkside Community of South Barrie* Walk to the beach on Wilkins walk or take a
50 Photos
Last Updated : 5 Days ago
12 Orleans Avenue, Simcoe, ON , MLS #S13761356 , Image - 1

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12 Orleans Avenue Innis-Shore, Barrie, Simcoe, ON MLS® S13761356

Residential Freehold (Detached)

$999900.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
*OPEN HOUSE SUNDAY SEP 20 AT 2-4 PM* Luxurious 3,100 SqFt Home! Stunning 4-bed + library (convertible 5th bed) on second floor home loaded with upgrad
30 Photos
Last Updated : 5 Days ago
7701 Doner Drive, Simcoe, ON , MLS #S13792886 , Image - 1

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7701 Doner Drive Washago, Severn, Simcoe, ON MLS® S13792886

Residential Freehold (Detached)

$1349900.0
  • 5 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Breathtaking Waterfront Retreat with Stunning Lake Views and Incredible Sunrises. Welcome to this beautifully fully renovated 5-bedroom waterfront hom
20 Photos
Last Updated : 5 Days ago
1454 Tomkins Road, Simcoe, ON , MLS #N13792744 , Image - 1

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1454 Tomkins Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13792744

Residential Freehold (Detached)

$1077000.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Built by the award-winning Bayview Wellington Homes, a trusted builder with over 40 years of experience, this exceptional, fully detached all-brick ho
49 Photos
Last Updated : 5 Days ago
2804 9th Line, Simcoe, ON , MLS #N13769878 , Image - 1

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2804 9th Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13769878

Residential Freehold (Detached)

$2650000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Spectacular 175-year-old, 5 bedroom, 4 bathroom century home situated on a private, stunning 10 acre lot featuring a picturesque pond & stream. Every
Open House : Sun Sep 27, 01:00 PM to 03:00 PM
35 Photos
Last Updated : 5 Days ago
4 Thomas Street, Simcoe, ON , MLS #N13719912 , Image - 1

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4 Thomas Street Glencairn, Adjala-Tosorontio, Simcoe, ON MLS® N13719912

Residential Freehold (Detached)

$949900.0
  • 5 Beds
  • 2 Baths
  • 3000-3500 sq-ft
Timeless Character, Nearly 3 Acres & Endless Possibilities! Welcome to this remarkable late-1800s century home, beautifully set on nearly 3 acres of p
43 Photos
Last Updated : 5 Days ago
29 SANFORD Circle, Simcoe, ON , MLS #S13783696 , Image - 1

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29 SANFORD Circle Centre Vespra, Springwater, Simcoe, ON MLS® S13783696

Residential Freehold (Detached)

$1450000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
WELCOME TO LUXURY SCALE IN SPRINGWATER. Nestled on a premium lot, 29 Sanford Circle represents a rare opportunity boasting a monumental 4,269 sq ft of
48 Photos
Last Updated : 5 Days ago
109 Brant Street E, Simcoe, ON , MLS #S13790002 , Image - 1

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109 Brant Street E Orillia, Simcoe, ON MLS® S13790002

Residential Freehold (Detached)

$749900.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Character. Space. Location. It's rare to get all three-especially in the North Ward. 1) Set on a quiet, treelined street just steps from Lake Couchich
35 Photos
Last Updated : 5 Days ago
1466 Broderick Street, Simcoe, ON , MLS #N13701598 , Image - 1

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1466 Broderick Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13701598

Residential Freehold (Detached)

$1299990.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to this beautifully upgraded premium 50' lot home offering over 3,700 sq. ft. of above-grade living space, blending luxury, comfort, and funct
43 Photos
Last Updated : 5 Days ago
3778 Vasey Road, Simcoe, ON , MLS #S13710142 , Image - 1

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3778 Vasey Road Rural Tay, Tay, Simcoe, ON MLS® S13710142

Residential Freehold (Detached)

$2474900.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
75 FORESTED ACRES of quiet luxury in Tay. Long, paved, tree-lined winding driveway leads to this UNIQUE CUSTOM EXECUTIVE HOME, offering unmatched priv
30 Photos
Last Updated : 5 Days ago
642-644 Bay Street, Simcoe, ON , MLS #S13532098 , Image - 1

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642-644 Bay Street Midland, Simcoe, ON MLS® S13532098

Residential Freehold (Duplex)

$419999.0
price drop iconPrice drop by 16.0%
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Attention Investors or First Time Home Buyers. Amazing Opportunity. Side by Side Duplex. Live in One Side and Rent Out the Other One. Or Rent Out Both
50 Photos
Last Updated : 6 Days ago
5494 Vasey Road, Simcoe, ON , MLS #S13667468 , Image - 1

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5494 Vasey Road Rural Tay, Tay, Simcoe, ON MLS® S13667468

Residential Freehold (Detached)

$899000.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Twenty-six acres of maple bush, open field and forested trail, with a creek along the front of the property and a century brick farmhouse at the cente
50 Photos
Last Updated : 6 Days ago
71 Newton Street, Simcoe, ON , MLS #S13774198 , Image - 1

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71 Newton Street Wellington, Barrie, Simcoe, ON MLS® S13774198

Residential Freehold (Detached)

$899999.0
  • 5 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 71 Newton Street - an extensively renovated 2-storey home offering exceptional versatility, modern updates, and outstanding income potentia
19 Photos
Last Updated : 6 Days ago
24 Twinleaf Crescent, Simcoe, ON , MLS #N13523148 , Image - 1

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24 Twinleaf Crescent Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N13523148

Residential Freehold (Detached)

$1737990.0
price drop iconPrice drop by 5.1%
  • 5 Beds
  • 5 Baths
  • 5000 + sq-ft
Welcome to this brand-new, never-lived-in 5-bedroom detached home by Tribute Communities, offering 5,100 sq. ft. of thoughtfully designed living space
Shortlisted Properties
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