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Detached Houses for Sale in Simcoe Under $5M - P35

Showing results 1021 - 1050 of 3363
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)
27 Photos
Last Updated : 6 Days ago
2070 Osbond Road, Simcoe, ON , MLS #N13785210 , Image - 1
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2070 Osbond Road Alcona, Innisfil, Simcoe, ON MLS® N13785210

Residential Freehold (Detached)

$1025000.0
  • 4 Beds
  • 3 Baths
  • 3000-3500 sq-ft
NEARLY 4,200 FINISHED SQ FT ON A CORNER LOT WITH A FINISHED WALK-UP BASEMENT, IN-LAW CAPABILITY & SOLAR INCOME POTENTIAL! Nearly 4,200 finished sq ft
50 Photos
Last Updated : 6 Days ago
4 Doner Street, Simcoe, ON , MLS #N13578674 , Image - 1

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4 Doner Street Alliston, New Tecumseth, Simcoe, ON MLS® N13578674

Residential Freehold (Detached)

$1029999.0
price drop iconPrice drop by 6.4%
  • 4 +2 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to this impressive 4 + 1 bedroom, 4-bathroom detached home in the heart of Alliston. A perfect blend of space, luxury, and versatility for tod
49 Photos
Last Updated : 6 Days ago
31 Crown Crescent, Simcoe, ON , MLS #N13693222 , Image - 1

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31 Crown Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13693222

Residential Freehold (Detached)

$1188800.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
An immaculate showcase of exceptional craftsmanship, elegant finishes and uncompromising pride of ownership, this cherished solid-brick family residen
44 Photos
Last Updated : 6 Days ago
43 Vanderpost Crescent, Simcoe, ON , MLS #N13785038 , Image - 1

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43 Vanderpost Crescent Thornton, Essa, Simcoe, ON MLS® N13785038

Residential Freehold (Detached)

$1649900.0
  • 4 +1 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to 43 Vanderpost Crescent, where generous living space, a peaceful country setting & everyday convenience come together in the sought-after co
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
37 Photos
Last Updated : 6 Days ago
413 Irwin Street, Simcoe, ON , MLS #S13646252 , Image - 1

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413 Irwin Street Midland, Simcoe, ON MLS® S13646252

Residential Freehold (Detached)

$545000.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 413 Irwin Street, Midland-a versatile 3-bedroom, 2-bathroom home offering in-law potential, a fully fenced backyard, and an unbeatable loca
35 Photos
Last Updated : 6 Days ago
904 Maplewood Drive N, Simcoe, ON , MLS #N13784990 , Image - 1

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904 Maplewood Drive N Alcona, Innisfil, Simcoe, ON MLS® N13784990

Residential Freehold (Detached)

$449000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
An Exceptional Opportunity Near The Lake! Welcome To 904 Maplewood Drive, A Charming Three-Bedroom Detached Bungalow Situated On An Impressive 50 X 16
49 Photos
Last Updated : 6 Days ago
258 James Street E, Simcoe, ON , MLS #S13774364 , Image - 1

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258 James Street E Orillia, Simcoe, ON MLS® S13774364

Residential Freehold (Detached)

$534900.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Don't Miss This Wonderful Opportunity To Own An Absolute Charmer! From The Moment You Pull Up In The Driveway, You Will Be Swept Off Your Feet By The
43 Photos
Last Updated : 6 Days ago
20 Highlands Crescent, Simcoe, ON , MLS #S13773478 , Image - 1

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20 Highlands Crescent Collingwood, Simcoe, ON MLS® S13773478

Residential Freehold (Detached)

$950000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Talk about a move-in ready home! Set out a south facing lot, 20 Highlands Crescent features 4 bedrooms (3+1), 3.5 bath, 2,176 sq ft above grade and ha
44 Photos
Last Updated : 6 Days ago
82 Bayview Drive, Simcoe, ON , MLS #S13784338 , Image - 1

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82 Bayview Drive Allandale Heights, Barrie, Simcoe, ON MLS® S13784338

Residential Freehold (Detached)

$699990.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Beautifully maintained and thoughtfully finished living spaces filled with an abundance of natural light fro
45 Photos
Last Updated : 6 Days ago
63 Oren Boulevard, Simcoe, ON , MLS #S13739746 , Image - 1

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63 Oren Boulevard Sunnidale, Barrie, Simcoe, ON MLS® S13739746

Residential Freehold (Detached)

$725500.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 63 Oren Boulevard - Tucked into a peaceful Barrie neighbourhood in the beautiful Sunnidale area, this surprisingly spacious 4-bedroom, 3-b
1 Photos
Last Updated : 6 Days ago
254 Simcoe Road, Simcoe, ON
254 Simcoe Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13008970

Residential Freehold (Detached)

$745000.0
price drop iconPrice drop by 5.1%
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Detached home in central Bradford with 2 kitchens. Hardwood floors throughout the main floor. Two entrances to lower level. Lower living room with abo
45 Photos
Last Updated : 6 Days ago
7826 25 Side Road, Simcoe, ON , MLS #N13783182 , Image - 1

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7826 25 Side Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13783182

Residential Freehold (Detached)

$1150000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Enjoy The Serenity And Privacy Of The Country! Close to Town. Built in 2019. This Open Concept Retreat Overlooking The Nottawasaga River. Bright and S
49 Photos
Last Updated : 6 Days ago
7697 County Road 56 N/A, Simcoe, ON , MLS #N13784620 , Image - 1

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7697 County Road 56 N/A Rural Essa, Essa, Simcoe, ON MLS® N13784620

Residential Freehold (Detached)

$1050000.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Gorgeous raised bungalow offering 3+1 bedrooms, set on approximately one-acre of picturesque property and pa
36 Photos
Last Updated : 6 Days ago
4654 Iron Bridge Lane, Simcoe, ON , MLS #S13784510 , Image - 1

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4654 Iron Bridge Lane Washago, Severn, Simcoe, ON MLS® S13784510

Residential Freehold (Detached)

$694000.0
  • 2 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Own a cottage that helps pay for itself with the rare opportunity to enjoy the best of both worlds, featurin
22 Photos
Last Updated : 6 Days ago
28 Harriet Street, Simcoe, ON , MLS #S13576262 , Image - 1

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28 Harriet Street Penetanguishene, Simcoe, ON MLS® S13576262

Residential Freehold (Detached)

$349900.0
price drop iconPrice drop by 12.5%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to this charming 3-bedroom bungalow nestled on a generous 49' x 165' lot in the heart of Penetanguishene. This home is an excellent opportunit
40 Photos
Last Updated : 6 Days ago
25 Maidens Crescent, Simcoe, ON , MLS #S13784394 , Image - 1

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25 Maidens Crescent Collingwood, Simcoe, ON MLS® S13784394

Residential Freehold (Detached)

$1129000.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to this beautifully maintained and thoughtfully upgraded family home, ideally situated in one of Collingwood's most sought-after neighbourhood
48 Photos
Last Updated : 6 Days ago
10 Jamieson Drive, Simcoe, ON , MLS #N13784366 , Image - 1

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10 Jamieson Drive Rosemont, Adjala-Tosorontio, Simcoe, ON MLS® N13784366

Residential Freehold (Detached)

$999900.0
  • 3 +3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Picture Sunday dinner where three generations are under one roof and nobody is stepping on anyone's toes. That is life in this two for one home. A pri
47 Photos
Last Updated : 6 Days ago
625 Aberdeen Boulevard, Simcoe, ON , MLS #S13678340 , Image - 1

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625 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13678340

Residential Freehold (Detached)

$1999000.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
A rare offering on Georgian Bay in Midland, just 90 minutes from the GTA: a private, deep-water lot with your own dock and full shoreline ownership ri
21 Photos
Last Updated : 6 Days ago
397 William Street, Simcoe, ON , MLS #S13683720 , Image - 1

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397 William Street Victoria Harbour, Tay, Simcoe, ON MLS® S13683720

Residential Freehold (Detached)

$479000.0
  • 3 +0 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Do you have a large family? This classic family home on an impressive sized lot in Victoria Harbour could easily be a 5 bedroom home making it ideal
44 Photos
Last Updated : 6 Days ago
710 Rose Lane, Simcoe, ON , MLS #N13463342 , Image - 1

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710 Rose Lane Alcona, Innisfil, Simcoe, ON MLS® N13463342

Residential Freehold (Detached)

$599000.0
price drop iconPrice drop by 7.8%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Just a short stroll from your private deeded beach access, this inviting property presents a wonderful opportunity to enjoy the best of lakeside livin
23 Photos
Last Updated : 6 Days ago
65 Delaney Crescent, Simcoe, ON , MLS #S13516460 , Image - 1

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65 Delaney Crescent Northwest, Barrie, Simcoe, ON MLS® S13516460

Residential Freehold (Detached)

$628000.0
price drop iconPrice drop by 13.7%
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Fully Renovated & Move-in Ready. Brand New 5-Appliances & Hood Fan And New Vinyl Floor Throughout. Bright & Spacious Detached Home on Quiet Crescent,
39 Photos
Last Updated : 6 Days ago
495 Shewfelt Crescent, Simcoe, ON , MLS #S13758512 , Image - 1

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495 Shewfelt Crescent Midland, Simcoe, ON MLS® S13758512

Residential Freehold (Detached)

$627777.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 495 Shewfelt Crescent, located in Midland's desirable west end in a quiet, sought-after neighbourhood. This well-maintained all-brick home
45 Photos
Last Updated : 6 Days ago
2215 Nevils Street, Simcoe, ON , MLS #N13645448 , Image - 1

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2215 Nevils Street Alcona, Innisfil, Simcoe, ON MLS® N13645448

Residential Freehold (Detached)

$849900.0
price drop iconPrice drop by 2.9%
  • 2 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Discover the perfect blend of luxury and versatility at 2215 Nevils Street. This meticulously maintained bungalow offers over 3,200 sq. ft. of profess
50 Photos
Last Updated : 6 Days ago
444 Maplegrove Avenue, Simcoe, ON , MLS #N13736846 , Image - 1

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444 Maplegrove Avenue Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13736846

Residential Freehold (Detached)

$948888.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to this spacious and beautifully maintained home in the heart of Bradford! Offering 3 generous bedrooms plus an additional bedroom in the fini
50 Photos
Last Updated : 6 Days ago
2199 Dawson Crescent, Simcoe, ON , MLS #N13775966 , Image - 1

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2199 Dawson Crescent Alcona, Innisfil, Simcoe, ON MLS® N13775966

Residential Freehold (Detached)

$1075000.0
  • 4 +1 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Welcome to complete elegance with this all brick stunning home in Innisfil which features 4 bedrooms and another in the basement for a total of 5 bedr
43 Photos
Last Updated : 6 Days ago
13009 County Road 16 Drive, Simcoe, ON , MLS #S13682474 , Image - 1

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13009 County Road 16 Drive Waubaushene, Tay, Simcoe, ON MLS® S13682474

Residential Freehold (Detached)

$1050000.0
price drop iconPrice drop by 4.5%
  • 3 +3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Custom built in 2020, this open-concept bungalow, is nestled on a premium, private 1.16-acre lot surrounded by mature trees and backing directly onto
48 Photos
Last Updated : 6 Days ago
270 Springfield Crescent, Simcoe, ON , MLS #S13660008 , Image - 1

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270 Springfield Crescent Stayner, Clearview, Simcoe, ON MLS® S13660008

Residential Freehold (Detached)

$749900.0
price drop iconPrice drop by 3.2%
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Privacy, space and an exceptional lot set this beautifully upgraded 3-bedroom, 3-bathroom home apart. Positioned on one of the largest pie-shaped lots
Open House : Sat Sep 26, 12:00 PM to 02:00 PM
50 Photos
Last Updated : 6 Days ago
35 48TH Street N, Simcoe, ON , MLS #S13566624 , Image - 1

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35 48TH Street N Wasaga Beach, Simcoe, ON MLS® S13566624

Residential Freehold (Detached)

$1200000.0
price drop iconPrice drop by 11.1%
  • 3 +3 Beds
  • 5 Baths
  • 1500-2000 sq-ft
Looking for a home that offers space, style, and an amazing location? This beautiful 6-bedroom, 4.5-bathroom home is just north of Mosley Street, only
47 Photos
Last Updated : 6 Days ago
70 Fairway Crescent, Simcoe, ON , MLS #S13023506 , Image - 1

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70 Fairway Crescent Wasaga Beach, Simcoe, ON MLS® S13023506

Residential Freehold (Detached)

$875000.0
price drop iconPrice drop by 7.9%
  • 3 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Enjoy golf course living with beautiful views every day. This home is ideally located on the 7th fairway of the Marlwood Golf Course, backing onto Mar
12 Photos
Last Updated : 7 Days ago
3908 Canal Road W, Simcoe, ON , MLS #S13783520 , Image - 1

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3908 Canal Road W Rural Severn, Severn, Simcoe, ON MLS® S13783520

Residential Freehold (Detached)

$635000.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
**WATERFRONT LIVING ON THE TRENT-SEVERN WATERWAY!**Welcome to **3908 West Canal Road in Severn**, an incredible opportunity to own your own piece of w
Shortlisted Properties
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