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5 Bedroom Houses for Sale in Simcoe Under $1.5M - P4

Showing results 91 - 120 of 151
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)
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
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
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
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
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
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
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
40 Photos
Last Updated : 34 Days ago
50 Concession Rd 2 N/A W, Simcoe, ON , MLS #S13076862 , Image - 1

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50 Concession Rd 2 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S13076862

Residential Freehold (Detached)

$1499000.0
  • 5 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Beautifully Updated 5-Bedroom, 3-Bathroom Home Set On A Rarely Offered 20.31-Acre Four-Season Property Overlooking The Wye River As It Winds Peacefull
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
26 Photos
Last Updated : 38 Days ago
125 Gardiner Drive N, Simcoe, ON , MLS #N13672032 , Image - 1

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125 Gardiner Drive N Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13672032

Residential Freehold (Detached)

$1385000.0
  • 5 +2 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to this exceptional 5-bedroom, 2-storey detached home, ideally situated on a premium lot backing directly onto a park. Offering an unbeatable
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
47 Photos
Last Updated : 40 Days ago
7 Wintergreen Lane, Simcoe, ON , MLS #N13612474 , Image - 1

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7 Wintergreen Lane Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N13612474

Residential Freehold (Detached)

$1489900.0
price drop iconPrice drop by 6.9%
  • 5 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to 7 Wintergreen Lane, an extraordinary executive residence in the prestigious Colgan Crossing community, where timeless architecture meets re
37 Photos
Last Updated : 40 Days ago
5 Oakwood Avenue N, Simcoe, ON , MLS #S13627170 , Image - 1

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5 Oakwood Avenue N Rural Tiny, Tiny, Simcoe, ON MLS® S13627170

Residential Freehold (Detached)

$1190000.0
  • 5 Beds
  • 5 Baths
  • 1500-2000 sq-ft
EVERY ONCE IN A LIFETIME A HOUSE QUALIFIES YOU AND THERE IS NOTHING YOU CAN DO ABOUT IT! WELL this is the ONE!! It will WOW you as you enter the home.
24 Photos
Last Updated : 40 Days ago
102 Westminster Circle, Simcoe, ON , MLS #S13662202 , Image - 1

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102 Westminster Circle Innis-Shore, Barrie, Simcoe, ON MLS® S13662202

Residential Freehold (Detached)

$948000.0
  • 5 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this spacious double garage detached home offering approximately 3,120 sq. ft. of well-designed living space. Featuring 5 generously sized
34 Photos
Last Updated : 40 Days ago
70 Ivy Lane, Simcoe, ON , MLS #S13641462 , Image - 1

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70 Ivy Lane Orillia, Simcoe, ON MLS® S13641462

Residential Freehold (Detached)

$630000.0
  • 5 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to Grape Island on the north edge of Lake Simcoe, in Orillia! This little piece of heaven is located on an island, only a 2 min boat ride from
9 Photos
Last Updated : 40 Days ago
6 Barrow Avenue, Simcoe, ON , MLS #N13645934 , Image - 1

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6 Barrow Avenue Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13645934

Residential Freehold (Detached)

$1329990.0
  • 5 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Buy Directly from the Builder! Beautiful 3,748 Sq. Ft. Inventory Family Home in Green Valley Estates. Discover exceptional space, style and luxury in
30 Photos
Last Updated : 40 Days ago
26 Cathedral Pines Road, Simcoe, ON , MLS #S13646460 , Image - 1

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26 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13646460

Residential Freehold (Detached)

$1349000.0
  • 5 Beds
  • 5 Baths
  • 2500-3000 sq-ft
TIMELESS ESTATE-STYLE LIVING IN DISTINGUISHED CATHEDRAL PINES WITH NEARLY 2,900 SQ FT ON OVER HALF AN ACRE! Hidden behind a veil of mature evergreens
Shortlisted Properties
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