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5 Bedroom Houses for Sale in Simcoe Under $10M - P5

Showing results 121 - 150 of 218
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)
50 Photos
Last Updated : 21 Days ago
30 Magnolia Avenue N, Simcoe, ON , MLS #N13695872 , Image - 1
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30 Magnolia Avenue N Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N13695872

Residential Freehold (Detached)

$1899000.0
  • 5 +0 Beds
  • 5 Baths
  • 5000 + sq-ft
Welcome to this impressive 5,000+ executive home in the heart of Tottenham, showcasing over $200,000 in upgrades and situated on a prime 73.24 X 179.2
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
49 Photos
Last Updated : 21 Days ago
176 Tigertail Crescent, Simcoe, ON , MLS #N13713854 , Image - 1

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176 Tigertail Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13713854

Residential Freehold (Detached)

$1499000.0
  • 5 +1 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Positioned on a premium 50-foot lot in one of Summerlyn's most sought-after crescents, this beautiful family home offers approximately 3,400 square fe
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
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
47 Photos
Last Updated : 23 Days ago
6576 Quarry Point Road, Simcoe, ON , MLS #S13663136 , Image - 1

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6576 Quarry Point Road Rural Ramara, Ramara, Simcoe, ON MLS® S13663136

Residential Freehold (Detached)

$1780000.0
  • 5 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Turnkey waterfront retreat on beautiful Lake Couchiching! Just 15 minutes from Orillia and minutes to Casino Rama, this exceptional four-season proper
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
48 Photos
Last Updated : 24 Days ago
102 Nottingham Road, Simcoe, ON , MLS #S13717160 , Image - 1

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102 Nottingham Road Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13717160

Residential Freehold (Detached)

$1099000.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this beautifully upgraded 5-bedroom, 4-bathroom detached home in Barrie South, built in 2022 and ideally situated on a corner lot backing/f
1 Photos
Last Updated : 24 Days ago
22 Olive Crescent, Simcoe, ON
22 Olive Crescent Orillia, Simcoe, ON MLS® S13649236

Residential Freehold (Fourplex)

$1179000.0
  • 5 +2 Beds
  • 4 Baths
  • 2500-3000 sq-ft
RENOVATED LEGAL FOURPLEX WITH MAJOR UPGRADES, LAKE SIMCOE ACROSS THE ROAD & INCOME-PRODUCING POTENTIAL! Secure an income-focused legal fourplex on nea
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
41 Photos
Last Updated : 24 Days ago
3965 Algoma Avenue, Simcoe, ON , MLS #N13717392 , Image - 1

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3965 Algoma Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13717392

Residential Freehold (Detached)

$2348800.0
  • 5 +1 Beds
  • 6 Baths
  • 3500-5000 sq-ft
DO NOT MISS THIS GREAT OPPORTUNITY!!! Welcome to this exceptional, upgraded custom bungaloft set on a rare 200 x 150 ft private lot surrounded by mat
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
39 Photos
Last Updated : 25 Days ago
2 Hook Court, Simcoe, ON , MLS #S13621808 , Image - 1

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2 Hook Court West Bayfield, Barrie, Simcoe, ON MLS® S13621808

Residential Freehold (Detached)

$1039900.0
  • 5 +3 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Discover this stunning oversized two-storey detached home with a double-car garage, ideally situated on a quiet court in the highly sought-after North
46 Photos
Last Updated : 25 Days ago
607 Cedarvale Drive, Simcoe, ON , MLS #N13713416 , Image - 1

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607 Cedarvale Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13713416

Residential Freehold (Detached)

$1950000.0
  • 5 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Big Cedar Point, Innisfil - Exceptional Lakefront Opportunity on Lake Simcoe. A rare offering at the very tip of sought-after Big Cedar Point. This pr
46 Photos
Last Updated : 25 Days ago
2981 Line 5 Line, Simcoe, ON , MLS #N13050382 , Image - 1

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2981 Line 5 Line Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13050382

Residential Freehold (Detached)

$1900000.0
price drop iconPrice drop by 11.5%
  • 5 +2 Beds
  • 5 Baths
  • 3000-3500 sq-ft
A rare opportunity to own a truly exceptional new custom-built home designed with multi-generational living in mind, blending thoughtful design, luxur
48 Photos
Last Updated : 26 Days ago
245 Jane Street, Simcoe, ON , MLS #S13532262 , Image - 1

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245 Jane Street Stayner, Clearview, Simcoe, ON MLS® S13532262

Residential Freehold (Detached)

$1149000.0
  • 5 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Exceptional legal duplex offering the perfect blend of family living and investment potential. The bright, open-concept main home features 3 spacious
47 Photos
Last Updated : 29 Days ago
222 Oak Street, Simcoe, ON , MLS #S13701580 , Image - 1

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222 Oak Street Collingwood, Simcoe, ON MLS® S13701580

Residential Freehold (Detached)

$2950000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Welcome to 222 Oak Street, where timeless elegance meets modern luxury in this custom-built North Oak home. Set on a fenced full town lot in downtown
50 Photos
Last Updated : 30 Days ago
153 Romanelli Crescent, Simcoe, ON , MLS #N13658530 , Image - 1

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153 Romanelli Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13658530

Residential Freehold (Detached)

$1349900.0
  • 5 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Welcome to 153 Romanelli Crescent, an impressive detached home offering approximately 3,000 sq. ft. of beautifully designed living space with 5 bedroo
31 Photos
Last Updated : 30 Days ago
17 Staglir Drive, Simcoe, ON , MLS #S13700360 , Image - 1

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17 Staglir Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13700360

Residential Freehold (Detached)

$1250000.0
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Escape The GTA Hustle For Ultimate Luxury Just Moments From The Crystal-Clear Shores Of Georgian Bay. Built In 2025, This Modern Custom Residence Offe
40 Photos
Last Updated : 30 Days ago
88 Cook Street, Simcoe, ON , MLS #S13696070 , Image - 1

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88 Cook Street Codrington, Barrie, Simcoe, ON MLS® S13696070

Residential Freehold (Detached)

$1250000.0
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Unique Custom Sprawling Modern Bungalow with Inground Pool, and triple car garage - ideally located in Barrie's East Ends Exclusive Area of Fine Homes
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
20 Photos
Last Updated : 31 Days ago
86 37th Street N, Simcoe, ON , MLS #S12691270 , Image - 1

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86 37th Street N Wasaga Beach, Simcoe, ON MLS® S12691270

Residential Freehold (Detached)

$1349000.0
price drop iconPrice drop by 12.3%
  • 5 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to 86 37th Street N!. This newly built custom home is a few minutes walk from Wasaga Beach! This meticulously crafted residence offers excepti
36 Photos
Last Updated : 31 Days ago
15 Radome Drive, Simcoe, ON , MLS #S13687428 , Image - 1

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15 Radome Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13687428

Residential Freehold (Detached)

$1995000.0
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to Eagles' Rest Estates-a master-planned Fernbrook Homes community where luxury meets nature! Outstanding curb appeal features a covered front
40 Photos
Last Updated : 32 Days ago
14 Mac Campbell Way, Simcoe, ON , MLS #N13689566 , Image - 1

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14 Mac Campbell Way Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13689566

Residential Freehold (Detached)

$1199990.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this newly built, beautifully appointed detached home offering spacious and modern living. Featuring 5 generously sized bedrooms, 4 full wa
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
50 Photos
Last Updated : 33 Days ago
3992 Penetanguishene Road, Simcoe, ON , MLS #S13542126 , Image - 1

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3992 Penetanguishene Road Hillsdale, Springwater, Simcoe, ON MLS® S13542126

Residential Freehold (Detached)

$1198000.0
  • 5 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome To Your Private Retreat In The Heart Of Nature. Situated On 8.06 Acres Of Complete Privacy, This Almost 2,500 Sq. Ft. Bungalow Offers An Incre
43 Photos
Last Updated : 33 Days ago
71 OAK LEA Boulevard, Simcoe, ON , MLS #S13132518 , Image - 1

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71 OAK LEA Boulevard Wasaga Beach, Simcoe, ON MLS® S13132518

Residential Freehold (Detached)

$1950000.0
  • 5 +0 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Experience the pinnacle of contemporary design in this newly built riverfront masterpiece boasting 4,000 above-ground square feet in a tranquil Wasaga
49 Photos
Last Updated : 34 Days ago
153 Creighton Street S, Simcoe, ON , MLS #S13480050 , Image - 1

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153 Creighton Street S Atherley, Ramara, Simcoe, ON MLS® S13480050

Residential Freehold (Detached)

$4899000.0
  • 5 Beds
  • 5 Baths
  • 5000 + sq-ft
Curated with pure intention, exceptionally executed - here's a spectacular opportunity to own one of Lake Simcoe's most admirable waterfront estates!
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
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