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Houses for Sale in Simcoe Under $5 Million - P33

Showing results 961 - 990 of 4523
Last Updated: November 10, 2026
  • New Listings
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  • Price(Hi-Lo)
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50 Photos
Last Updated : 6 Days ago
4254 Forest Wood Drive, Simcoe, ON , MLS #S14117132 , Image - 1
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4254 Forest Wood Drive Rural Severn, Severn, Simcoe, ON MLS® S14117132

Residential Freehold (Detached)

$949900.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to the highly coveted neighbourhood of Forest Wood Drive! Situated on a quiet dead-end road just steps to Orillia, this gorgeous and meticulou
35 Photos
Last Updated : 6 Days ago
52 Thomas Drive, Simcoe, ON , MLS #S13881380 , Image - 1

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52 Thomas Drive Collingwood, Simcoe, ON MLS® S13881380

Residential Freehold (Att/Row/Townhouse)

$739900.0
  • 1 +3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Ideally located between downtown Collingwood and Blue Mountain ski hills, 52 Thomas Drive is a freehold townhome ( no condo fees) sitting on a landsca
27 Photos
Last Updated : 6 Days ago
126 29th Street N, Simcoe, ON , MLS #S14138370 , Image - 1

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126 29th Street N Wasaga Beach, Simcoe, ON MLS® S14138370

Residential Freehold (Detached)

$967000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Embrace an exceptional lifestyle just steps from the water, where beautiful waterfront surroundings and endl
49 Photos
Last Updated : 6 Days ago
8168 Laidlaw Avenue, Simcoe, ON , MLS #S14112684 , Image - 1

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8168 Laidlaw Avenue Rural Ramara, Ramara, Simcoe, ON MLS® S14112684

Residential Freehold (Detached)

$690000.0
  • 3 +0 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to your waterfront home set directly on the Severn River, this beautifully renovated 3-bedroom, 2-bathroom property offers the best of cottage
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
35 Photos
Last Updated : 6 Days ago
1060 HARBOURVIEW Drive, Simcoe, ON , MLS #S14146796 , Image - 1

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1060 HARBOURVIEW Drive Midland, Simcoe, ON MLS® S14146796

Residential Freehold (Detached)

$539777.0
  • 3 +1 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 1060 Harbourview Drive in Midland, a great family home situated on a generous 50' x 200' in-town lot close to local amenities and the beaut
20 Photos
Last Updated : 6 Days ago
90 Burke Street, Simcoe, ON , MLS #S13853022 , Image - 1

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Unit-18, 90 Burke Street Penetanguishene, Simcoe, ON MLS® S13853022

Residential Condo & Other (Condo Townhouse)

$649900.0
price drop iconPrice drop by 4.4%
  • 2 +2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome to your easy, carefree living in popular Summer Haven adult lifestyle community located in a prime location. This turn-key home has been imma
20 Photos
Last Updated : 6 Days ago
255 Eighth Street, Simcoe, ON , MLS #S14095120 , Image - 1

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255 Eighth Street Midland, Simcoe, ON MLS® S14095120

Residential Freehold (Detached)

$579000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
A Place to Call Home! This affordable classic solid-built brick home is located on a Rare 75 x 100 ft lot!!! in the Prime West-End of Midland. Fresh
35 Photos
Last Updated : 6 Days ago
1784 Tiny Beaches Road S, Simcoe, ON , MLS #S13733826 , Image - 1

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1784 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13733826

Residential Freehold (Detached)

$1490000.0
  • 5 +2 Beds
  • 2 Baths
  • 2000-2500 sq-ft
A gorgeous Georgian Bay waterfront where a sandy beach and a spacious family retreat come together in one of Southern Tiny's most desirable shoreline
50 Photos
Last Updated : 6 Days ago
9 Howard Drive, Simcoe, ON , MLS #S14106672 , Image - 1

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9 Howard Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14106672

Residential Freehold (Detached)

$1249900.0
  • 4 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
HARBOURWOOD ESTATES | If you've been dreaming of the perfect combination of location, lot size, and a stunningly updated family home, it's time to wak
47 Photos
Last Updated : 6 Days ago
1043 Hurlwood Lane, Simcoe, ON , MLS #S14014428 , Image - 1

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1043 Hurlwood Lane Rural Severn, Severn, Simcoe, ON MLS® S14014428

Residential Freehold (Detached)

$1399500.0
price drop iconPrice drop by 3.4%
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 1043 Hurlwood Lane in Severn Township, a stunning estate bungalow located just minutes outside of Orillia. Proudly owned by the same owners
40 Photos
Last Updated : 6 Days ago
4200 Pine Valley Lane, Simcoe, ON , MLS #S14119390 , Image - 1

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4200 Pine Valley Lane Rural Severn, Severn, Simcoe, ON MLS® S14119390

Residential Freehold (Detached)

$1279000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 4200 Pine Valley Lane, in Severn, Ontario. Located in an exclusive estate neighbourhood just minutes from downtown Orillia, this impressiv
25 Photos
Last Updated : 6 Days ago
33B Cundles Road E, Simcoe, ON , MLS #S13855748 , Image - 1

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33B Cundles Road E Cundles East, Barrie, Simcoe, ON MLS® S13855748

Residential Freehold (Semi-Detached )

$549000.0
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Vacant and move in ready 4 bedroom home with over 1500 square feet of living space complete with large 20'9 x 12'2 finished room in the basement. Bri
37 Photos
Last Updated : 6 Days ago
10 Rutherford Road, Simcoe, ON , MLS #N14126064 , Image - 1

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10 Rutherford Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N14126064

Residential Freehold (Semi-Detached )

$799900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 10 Rutherford Road in Bradford's desirable West Park Village! With just under 2,000 sqft of total living space, this well-appointed 3-bedro
20 Photos
Last Updated : 6 Days ago
36 Sanford Street, Simcoe, ON , MLS #S13808718 , Image - 1

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36 Sanford Street Sanford, Barrie, Simcoe, ON MLS® S13808718

Residential Freehold (Detached)

$459900.0
price drop iconPrice drop by 6.1%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
BARRIE BUNGALOW! Welcome to this charming move-in ready 3-bedroom, 1-bath bungalow in a desirable Barrie neighbourhood. Bright and inviting, this well
10 Photos
Last Updated : 6 Days ago
1017 Line 8 North Line, Simcoe, ON , MLS #S13655598 , Image - 1

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1017 Line 8 North Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13655598

Residential Freehold (Vacant Land)

$479900.0
*** AN EXCEPTIONAL OPPORTUNITY FOR BUILDERS, DEVELOPERS, OR ANYONE READY TO CREATE THEIR DREAM HOME * THIS PICTURESQUE 2.03-ACRE PARCEL (285 X 310) SI
50 Photos
Last Updated : 6 Days ago
2021 Beaver Dam Road, Simcoe, ON , MLS #S14029912 , Image - 1

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2021 Beaver Dam Road Rural Severn, Severn, Simcoe, ON MLS® S14029912

Residential Freehold (Detached)

$1649000.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
SEVERN RIVER - A distinctive waterfront retreat offering 487 ft of shoreline as per MPAC, extensive privacy and direct access to The Trent-Severn Wate
50 Photos
Last Updated : 6 Days ago
508 Grove Street E, Simcoe, ON , MLS #S14146338 , Image - 1

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508 Grove Street E Grove East, Barrie, Simcoe, ON MLS® S14146338

Residential Freehold (Detached)

$908800.0
  • 4 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
A Rare, Turnkey Gem In The Heart Of Grove East, Ready For Your Family To Move Right In And Enjoy! Beautifully Renovated To Like-New Condition With A S
Open House : Sat Nov 14, 02:00 PM to 05:00 PM
23 Photos
Last Updated : 6 Days ago
40 Baynes Way, Simcoe, ON , MLS #N13859646 , Image - 1

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Unit-7, 40 Baynes Way Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13859646

Residential Condo & Other (Condo Townhouse)

$695888.0
price drop iconPrice drop by 4.7%
  • 3 Beds
  • 3 Baths
  • 1800-1999 sq-ft
Welcome To This Stunning New-Build Condo Townhouse Located In The Vibrant And Growing Community Of Bradford! Spanning An Impressive 2,469 Sq Ft (Both
8 Photos
Last Updated : 6 Days ago
440 Gill Street, Simcoe, ON , MLS #S13845032 , Image - 1

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440 Gill Street Orillia, Simcoe, ON MLS® S13845032

Residential Freehold (Detached)

$425000.0
  • 4 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Opportunity awaits. This classic brick 2-storey home is ideal for first time buyers, savvy rental investors or young families looking to move into a
50 Photos
Last Updated : 6 Days ago
20 Northland Court, Simcoe, ON , MLS #S13719216 , Image - 1

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20 Northland Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13719216

Residential Freehold (Detached)

$1499000.0
  • 4 +1 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Welcome to the highly sought-after community of Craighurst Crossings, where this brand-new, never-lived-in Caston model home offers exceptional upgrad
Open House : Sun Nov 15, 12:00 PM to 02:00 PM
27 Photos
Last Updated : 6 Days ago
3278 Russell Drive, Simcoe, ON , MLS #S14146256 , Image - 1

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3278 Russell Drive Port Severn, Severn, Simcoe, ON MLS® S14146256

Residential Freehold (Detached)

$899900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
This beautifully designed two year old 3-bedroom, 3-bathroom home offers the perfect blend of comfort, style and privacy. From the moment you step ins
50 Photos
Last Updated : 6 Days ago
65 Cindy Lane, Simcoe, ON , MLS #N14140724 , Image - 1

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65 Cindy Lane Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N14140724

Residential Freehold (Detached)

$1124990.0
  • 3 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Escape to the peace and beauty of country living on this stunning 1.15 acre property in thecharming community of Lisle. Built in 2012, this beautifull
35 Photos
Last Updated : 6 Days ago
61 Strabane Avenue, Simcoe, ON , MLS #S14144874 , Image - 1

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61 Strabane Avenue Codrington, Barrie, Simcoe, ON MLS® S14144874

Residential Freehold (Detached)

$659900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 61 Strabane Avenue, a beautifully maintained brick bungalow in Barrie's desirable east end. The main level features an updated kitchen, a b
26 Photos
Last Updated : 6 Days ago
177 King Street S, Simcoe, ON , MLS #N14021554 , Image - 1

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177 King Street S Alliston, New Tecumseth, Simcoe, ON MLS® N14021554

Residential Freehold (Detached)

$729900.0
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome home to this beautifully updated backsplit located in the heart of Alliston! Perfect for family living and effortless entertaining, the fully
49 Photos
Last Updated : 6 Days ago
5 Loftus Road, Simcoe, ON , MLS #S14146082 , Image - 1

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5 Loftus Road Rural Springwater, Springwater, Simcoe, ON MLS® S14146082

Residential Freehold (Detached)

$1574900.0
  • 3 +4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Private. Refined. Spacious. Set among 1.5 acres of mature forest, this beautifully appointed bungalow offers the rare combination of privacy, space, a
27 Photos
Last Updated : 6 Days ago
3 Sawmill Road, Simcoe, ON , MLS #S13449054 , Image - 1

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Unit-2, 3 Sawmill Road Ardagh, Barrie, Simcoe, ON MLS® S13449054

Residential Condo & Other (Condo Apartment)

$369900.0
price drop iconPrice drop by 7.5%
  • 2 Beds
  • 1 Baths
  • 1200-1399 sq-ft
Why rent when you can own? Welcome to 3 Sawmill Road, Unit 2, a bright and inviting 2-bedroom, 1-bathroom condo in Barrie's highly sought-after Timber
28 Photos
Last Updated : 6 Days ago
39 Highcroft Road, Simcoe, ON , MLS #S13855002 , Image - 1

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39 Highcroft Road Allandale Heights, Barrie, Simcoe, ON MLS® S13855002

Residential Freehold (Duplex)

$649900.0
price drop iconPrice drop by 7.1%
  • 3 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
A HOME THAT HELPS WITH THE MORTGAGE! Welcome to 39 Highcroft Road, a legal 3+2 bedroom semi-detached duplex offering a smart opportunity to enjoy a sp
42 Photos
Last Updated : 6 Days ago
146 Mary Street, Simcoe, ON , MLS #S14146040 , Image - 1

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146 Mary Street Creemore, Clearview, Simcoe, ON MLS® S14146040

Residential Freehold (Detached)

$999000.0
  • 3 +3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Discover exceptional space, quality, and versatility in the heart of Creemore! Built in 2023, this custom raised bungalow offers nearly 3,400 sq. ft.
23 Photos
Last Updated : 6 Days ago
2 Laguna Parkway, Simcoe, ON , MLS #S14114540 , Image - 1

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Unit-1, 2 Laguna Parkway Brechin, Ramara, Simcoe, ON MLS® S14114540

Residential Condo & Other (Condo Townhouse)

$498000.0
  • 3 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Luxury Waterfront Living in Lagoon City! This stunning, newly renovated 3-bedroom end-unit townhouse offers an exceptional blend of modern elegance, c
50 Photos
Last Updated : 6 Days ago
3511 Rainbow Valley Road W, Simcoe, ON , MLS #S13884454 , Image - 1

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3511 Rainbow Valley Road W Rural Springwater, Springwater, Simcoe, ON MLS® S13884454

Residential Freehold (Detached)

$1350000.0
price drop iconPrice drop by 14.3%
  • 6 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Step into contemporary elegance with this newly built ( 2024 ) 5+1 - bedroom and 3+2 - bathroom home, perfectly situated on a large ( 4.7 acre ) priva
Shortlisted Properties
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