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Houses for Sale in Simcoe Under $5 Million - P36

Showing results 1051 - 1080 of 5130
Last Updated: August 12, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
40 Photos
Last Updated : 5 Days ago
3769 Sunbank Crescent, Simcoe, ON , MLS #S13591770 , Image - 1
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3769 Sunbank Crescent West Shore, Severn, Simcoe, ON MLS® S13591770

Residential Freehold (Detached)

$849000.0
  • 4 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to 3769 Sunbank Crescent, a never-lived-in (2023) luxury detached home situated on a premium pie-shaped lot in the sought-after Paradise by th
32 Photos
Last Updated : 5 Days ago
5317 County 9 Road, Simcoe, ON , MLS #S13566976 , Image - 1

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5317 County 9 Road New Lowell, Clearview, Simcoe, ON MLS® S13566976

Residential Freehold (Detached)

$579000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
This 3 bedroom home sits on a large lot in one of the area's most sought after communities, just a short walk to the school, library, park, and only m
43 Photos
Last Updated : 5 Days ago
12 LANKIN Boulevard, Simcoe, ON , MLS #S13459880 , Image - 1

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Unit-31, 12 LANKIN Boulevard Orillia, Simcoe, ON MLS® S13459880

Residential Condo & Other (Condo Townhouse)

$418880.0
  • 3 +0 Beds
  • 1 Baths
  • 1200-1399 sq-ft
SOLD CONDITIONAL PENDING DEPOSIT...Discover the perfect blend of comfort, value, and lakeside living in this charming 3-bedroom townhome at the revita
23 Photos
Last Updated : 5 Days ago
34 Spry Lane, Simcoe, ON , MLS #S13593912 , Image - 1

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34 Spry Lane Innis-Shore, Barrie, Simcoe, ON MLS® S13593912

Residential Freehold (Att/Row/Townhouse)

$550000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Contemporary Townhome in a Thriving Community. Welcome to this beautifully designed 3-bedroom, 3-bathroom townhome with den which could be turned into
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
46 Photos
Last Updated : 5 Days ago
1284 Rumney Road, Simcoe, ON , MLS #S13567640 , Image - 1

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1284 Rumney Road Rural Tay, Tay, Simcoe, ON MLS® S13567640

Residential Freehold (Farm)

$2249000.0
  • 4 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Welcome to a truly breathtaking estate on a high point looking westwards. 30 minutes from Barrie, 20 minutes to Georgian Bay beaches 10 minutes to Mid
30 Photos
Last Updated : 5 Days ago
1295 Hilltop Road, Simcoe, ON , MLS #S13648830 , Image - 1

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1295 Hilltop Road Rural Severn, Severn, Simcoe, ON MLS® S13648830

Residential Freehold (MobileTrailer)

$255000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Tucked away at the very end of the street with no rear neighbours, this hidden gem overlooks an open meadow,
50 Photos
Last Updated : 5 Days ago
7 Duquette Court, Simcoe, ON , MLS #S13648816 , Image - 1

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7 Duquette Court Rural Tiny, Tiny, Simcoe, ON MLS® S13648816

Residential Freehold (Detached)

$2250000.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Exceptional custom-built home offering over 3,800 square feet of beautifully finished living space, showcasi
50 Photos
Last Updated : 5 Days ago
114 11th Line S, Simcoe, ON , MLS #S13572456 , Image - 1

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114 11th Line S Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13572456

Residential Freehold (Detached)

$1299000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Spacious brick ranch bungalow on a 1.485 acre lot, surrounded by mixed forest and adjacent to a wetland, offering the privacy you have been longing fo
42 Photos
Last Updated : 5 Days ago
3866 Glenrest Drive, Simcoe, ON , MLS #S13439436 , Image - 1

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3866 Glenrest Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13439436

Residential Freehold (Detached)

$1650000.0
price drop iconPrice drop by 15.4%
  • 3 Beds
  • 3 Baths
  • 2500-3000 sq-ft
First time offered for sale: this beautiful post & beam waterfront home on Lake Simcoe, minutes east of Orillia. Custom built in 1996, this home is ar
33 Photos
Last Updated : 5 Days ago
9 WHITE PINES Trail, Simcoe, ON , MLS #S13648782 , Image - 1

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9 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S13648782

Residential Freehold (MobileTrailer)

$185000.0
  • 2 +0 Beds
  • 1 Baths
  • < 700 sq-ft
Hear the waves of Georgian Bay from this perfect seasonal retreat in the highly sought-after Countrylife Resort. Open from May 1st to November 15th, t
2 Photos
Last Updated : 5 Days ago
1366 Wilson Point Road, Simcoe, ON , MLS #S13430030 , Image - 1
1366 Wilson Point Road Rural Severn, Severn, Simcoe, ON MLS® S13430030

Residential Freehold (Vacant Land)

$275000.0
Attention investors. looking for a chance to build a triplex or more ? the neighbor just built two 4 plexes and one approved for a four plex.
36 Photos
Last Updated : 5 Days ago
153 Matchedash Street N, Simcoe, ON , MLS #S13626142 , Image - 1

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153 Matchedash Street N Orillia, Simcoe, ON MLS® S13626142

Residential Freehold (Detached)

$795000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Located in one of Orillia's most established neighborhoods in the prestigious area known as the old north ward Orillia. A desirable historic area sou
28 Photos
Last Updated : 5 Days ago
4258 Canal Road, Simcoe, ON , MLS #S13648744 , Image - 1

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4258 Canal Road Rural Severn, Severn, Simcoe, ON MLS® S13648744

Residential Freehold (Rural Residential)

$329900.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
SEVERN RIVER Escape - part of the renowned Trent-Severn Waterway, where endless days of Boating, Fishing, Swimming, and simply Relaxing await. This Ch
43 Photos
Last Updated : 5 Days ago
108 Durham Avenue, Simcoe, ON , MLS #S13223302 , Image - 1

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108 Durham Avenue Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13223302

Residential Freehold (Detached)

$784900.0
price drop iconPrice drop by 9.2%
  • 4 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
108 Durham does something most detached homes in Barrie can't: it gives you a full four-bedroom family home and a separate in-law suite under one roof
50 Photos
Last Updated : 5 Days ago
24 Ramblings Way, Simcoe, ON , MLS #S13648632 , Image - 1

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24 Ramblings Way
Unit-706, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S13648632

Residential Condo & Other (Condo Apartment)

$729900.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to Bayview Tower! This lovely 3 bedroom unit on the 7th floor brings in ample natural light with large windows looking out over Blue Mountain
45 Photos
Last Updated : 5 Days ago
17 Church Street, Simcoe, ON , MLS #N13247124 , Image - 1

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17 Church Street Cookstown, Innisfil, Simcoe, ON MLS® N13247124

Residential Freehold (Detached)

$600000.0
price drop iconPrice drop by 7.7%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Looking for a classic small town vibe? Cookstown is the place for you! Step back in time with this character-filled century home nestled in the quaint
43 Photos
Last Updated : 5 Days ago
190 Mackenzie Street, Simcoe, ON , MLS #N13633166 , Image - 1

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190 Mackenzie Street Alliston, New Tecumseth, Simcoe, ON MLS® N13633166

Residential Freehold (Detached)

$799000.0
  • 4 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Car enthusiasts, hobbyists, or anyone in need of extra workspace will be blown away by the show-stopping heated and insulated 2-car garage/shop! This
26 Photos
Last Updated : 5 Days ago
74 Ruby Ridge, Simcoe, ON , MLS #S13648262 , Image - 1

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74 Ruby Ridge Sugarbush, Oro-Medonte, Simcoe, ON MLS® S13648262

Residential Freehold (Detached)

$1098000.0
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 74 Ruby Ridge-a brand-new, never-lived-in 2,170 sq. ft. bungalow set on a massive, picturesque 0.7-acre greenbelt lot (99' x 310') in beaut
50 Photos
Last Updated : 5 Days ago
215 Mary Anne Drive, Simcoe, ON , MLS #S13634290 , Image - 1

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215 Mary Anne Drive Painswick North, Barrie, Simcoe, ON MLS® S13634290

Residential Freehold (Detached)

$819000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Rarely does a property offer this much space, privacy and possibility while remaining just minutes from everything Barrie has to offer.Set on an extra
22 Photos
Last Updated : 5 Days ago
39 Ferndale Drive S, Simcoe, ON , MLS #S13598406 , Image - 1

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Unit-312, 39 Ferndale Drive S Ardagh, Barrie, Simcoe, ON MLS® S13598406

Residential Condo & Other (Condo Apartment)

$499990.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Rarely offered corner suite with over 1,464 sq ft of well designed living space, the floorplan buyers wait for. Three generously sized bedrooms and tw
19 Photos
Last Updated : 5 Days ago
34 McDonald Street, Simcoe, ON , MLS #N13619282 , Image - 1

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34 McDonald Street Alliston, New Tecumseth, Simcoe, ON MLS® N13619282

Residential Freehold (Detached)

$599900.0
  • 2 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to this 2+1 bedroom brick bungalow, ideally situated in a desirable Alliston neighbourhood just blocks from the local high school.This invitin
40 Photos
Last Updated : 5 Days ago
174 Green Briar Road, Simcoe, ON , MLS #N13410202 , Image - 1

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Unit-3, 174 Green Briar Road Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13410202

Residential Condo & Other (Detached Condo)

$769900.0
price drop iconPrice drop by 1.3%
  • 2 +1 Beds
  • 4 Baths
  • 1400-1599 sq-ft
Whether commuting or retiring, this home offers the perfect balance of relaxation and low-maintenance living. Spend less time on upkeep and more time
48 Photos
Last Updated : 5 Days ago
31 Prince Drive, Simcoe, ON , MLS #N13108416 , Image - 1

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31 Prince Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13108416

Residential Freehold (Detached)

$985000.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to your dream home! This turn key gorgeous, updated detached residence is nestled in one of Bradford's most serene neighborhoods. Offering a p
33 Photos
Last Updated : 5 Days ago
3408 Coronation Avenue, Simcoe, ON , MLS #S13612666 , Image - 1

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3408 Coronation Avenue West Shore, Severn, Simcoe, ON MLS® S13612666

Residential Freehold (Detached)

$509999.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to this charming, move-in ready home nestled in a beautiful lakeside community just minutes from Orillia. Situated on a generous 52 ft x 136 f
1 Photos
Last Updated : 5 Days ago
252 Penetanguishene Road, Simcoe, ON
Unit-10, 252 Penetanguishene Road Georgian Drive, Barrie, Simcoe, ON MLS® S13648044

Residential Condo & Other (Condo Townhouse)

$469900.0
  • 4 Beds
  • 4 Baths
  • 1200-1399 sq-ft
Fantastic investment opportunity in Barrie's Georgian Drive community. This efficient 1,400 sq ft condo townhouse features a layout optimized for high
41 Photos
Last Updated : 5 Days ago
1183 Everton Road, Simcoe, ON , MLS #S13536426 , Image - 1

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1183 Everton Road Midland, Simcoe, ON MLS® S13536426

Residential Freehold (Detached)

$699900.0
  • 2 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Well-maintained and move-in ready home featuring bright open-concept living spaces, a cozy gas fireplace for
44 Photos
Last Updated : 5 Days ago
2019 Lilac Drive, Simcoe, ON , MLS #N13647936 , Image - 1

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2019 Lilac Drive Alcona, Innisfil, Simcoe, ON MLS® N13647936

Residential Freehold (Detached)

$2299999.0
  • 4 +1 Beds
  • 6 Baths
  • 3500-5000 sq-ft
Welcome to 2019 Lilac Dr, an absolutely stunning CUSTOM BUILT 4+1 bedroom residence in Alcona, just minutes from the beach. Built in 2022 and situated
34 Photos
Last Updated : 5 Days ago
49 Paisley Drive, Simcoe, ON , MLS #N13558458 , Image - 1

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49 Paisley Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13558458

Residential Freehold (Semi-Detached )

$939888.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Top Reasons To Buy 1) Brand New Semi Located In The Heart Of Bradford, Summerlyn Village With $$50,000 Worth Of Upgrades. Open Concept With Soaring 9
1 Photos
Last Updated : 5 Days ago
59 Therrien Court, Simcoe, ON
59 Therrien Court Penetanguishene, Simcoe, ON MLS® S13647856

Residential Freehold (Semi-Detached )

$399900.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Calling all first-time buyers or savvy investors! This handyman special offers a fantastic opportunity to create your dream home. With 4 Bedrooms, 2 b
49 Photos
Last Updated : 5 Days ago
8168 Laidlaw Avenue, Simcoe, ON , MLS #S13574590 , Image - 1

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8168 Laidlaw Avenue Rural Ramara, Ramara, Simcoe, ON MLS® S13574590

Residential Freehold (Detached)

$799000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this fully renovated four-season retreat offering over 70 feet of pristine frontage on the beautiful Severn River. Completely transformed,
Shortlisted Properties
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