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Houses for Sale in Simcoe Under $5 Million - P39

Showing results 1141 - 1170 of 5157
Last Updated: September 26, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
41 Photos
Last Updated : 4 Days ago
1376 Rankin Way, Simcoe, ON , MLS #N13708418 , Image - 1
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1376 Rankin Way Alcona, Innisfil, Simcoe, ON MLS® N13708418

Residential Freehold (Detached)

$685000.0
price drop iconPrice drop by 2.0%
  • 4 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to 1376 Rankin Way - Set on a quiet street just minutes from Innisfil Beach, this 2-storey brick home offers 1,900 sq ft of above-grade living
Open House : Sun Sep 27, 01:00 PM to 03:00 PM
47 Photos
Last Updated : 4 Days ago
3793 Mangusta Court, Simcoe, ON , MLS #N13811564 , Image - 1

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3793 Mangusta Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13811564

Residential Freehold (Att/Row/Townhouse)

$1549000.0
  • 3 Beds
  • 5 Baths
  • 2000-2500 sq-ft
IT'S ALL ABOUT THE VIEW! Welcome to an extraordinary waterfront residence in the heart of Friday Harbour Resort where refined luxury meets the vibranc
Open House : Sun Sep 27, 11:00 AM to 03:00 PM
49 Photos
Last Updated : 4 Days ago
147 Anne Street N, Simcoe, ON , MLS #S13695208 , Image - 1

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147 Anne Street N Sunnidale, Barrie, Simcoe, ON MLS® S13695208

Residential Freehold (Detached)

$828888.0
price drop iconPrice drop by 0.7%
  • 4 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
**Three Above-Grade Levels. Three Private Entrances. Endless Possibilities.** Backing onto a peace ful forested ravine in Barrie's sought-after Sunnid
35 Photos
Last Updated : 4 Days ago
69 Smith Street, Simcoe, ON , MLS #N13716550 , Image - 1

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69 Smith Street Alliston, New Tecumseth, Simcoe, ON MLS® N13716550

Residential Freehold (Detached)

$649000.0
price drop iconPrice drop by 3.0%
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this adorable and affordable 2-storey home situated on a quiet, family-friendly street! This charming home features 3 spacious bedrooms, 2
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
28 Photos
Last Updated : 4 Days ago
9771 Beachwood Road, Simcoe, ON , MLS #S13684022 , Image - 1

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9771 Beachwood Road Collingwood, Simcoe, ON MLS® S13684022

Residential Freehold (Detached)

$499900.0
price drop iconPrice drop by 5.7%
  • 4 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 9771 Beachwood Rd - a rare opportunity combining four-season living, an impressive 60' x 250' mature-treed lot and exciting long-term poten
47 Photos
Last Updated : 4 Days ago
291 Third Street, Simcoe, ON , MLS #S13811550 , Image - 1

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291 Third Street Collingwood, Simcoe, ON MLS® S13811550

Residential Freehold (Detached)

$2499000.0
  • 5 Beds
  • 3 Baths
  • 3000-3500 sq-ft
**A Rare Collingwood Masterpiece - Historic Character, Modern Luxury & Unparalleled Potential!** This extraordinary 1894 red brick estate is set on a
41 Photos
Last Updated : 4 Days ago
43 Dunnett Drive, Simcoe, ON , MLS #S13607834 , Image - 1

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43 Dunnett Drive Ardagh, Barrie, Simcoe, ON MLS® S13607834

Residential Freehold (Detached)

$1125000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 43 Dunnett Drive, a truly turn-key home in the highly sought-after Ardagh Bluffs neighbourhood of Barrie's southwest end. Offering over 3,0
43 Photos
Last Updated : 4 Days ago
22 Maple Crown Terrace, Simcoe, ON , MLS #S13663730 , Image - 1

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22 Maple Crown Terrace Innis-Shore, Barrie, Simcoe, ON MLS® S13663730

Residential Freehold (Detached)

$869900.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Space, flexibility & extensive 2026 updates come together at 22 Maple Crown Terrace in Barrie's Innis-Shore community. Built by Zancor Homes, this 4-b
30 Photos
Last Updated : 4 Days ago
583 Aberdeen Boulevard, Simcoe, ON , MLS #S13717354 , Image - 1

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583 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13717354

Residential Freehold (Vacant Land)

$800000.0
Welcome to 583 Aberdeen Boulevard, a prime waterfront building lot with breathtaking views of Georgian Bay and nestled among luxury waterfront homes i
49 Photos
Last Updated : 4 Days ago
1273 HAWK RIDGE Crescent, Simcoe, ON , MLS #S13778840 , Image - 1

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1273 HAWK RIDGE Crescent Rural Severn, Severn, Simcoe, ON MLS® S13778840

Residential Freehold (Detached)

$1499000.0
  • 3 +3 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to 1273 Hawk Ridge Cres. this spectacular luxury bungalow is located in the sought after community of Hawk Ridge Estates. This upscale custom
Open House : Sun Sep 27, 12:00 PM to 02:00 PM
30 Photos
Last Updated : 4 Days ago
44 Ferguson Drive, Simcoe, ON , MLS #S13783702 , Image - 1

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44 Ferguson Drive Northwest, Barrie, Simcoe, ON MLS® S13783702

Residential Freehold (Duplex)

$599900.0
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
This legal duplex keeps things simple: two units, a convenient location, and options for how you use it. The main floor offers 2 bedrooms, while the l
21 Photos
Last Updated : 4 Days ago
6047 Highway 89 N/A, Simcoe, ON , MLS #N13811450 , Image - 1

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Unit-51, 6047 Highway 89 N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13811450

Residential Freehold (MobileTrailer)

$225000.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Welcome to your new home in, a peaceful community ideally located between charming Cookstown and growing Alliston. This inviting modular home offers c
25 Photos
Last Updated : 4 Days ago
22 Creighton Street S, Simcoe, ON , MLS #S13735156 , Image - 1

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22 Creighton Street S Orillia, Simcoe, ON MLS® S13735156

Residential Freehold (Detached)

$549000.0
price drop iconPrice drop by 2.8%
  • 2 Beds
  • 1 Baths
  • 1100-1500 sq-ft
A charming bungalow with a massive heated shop, two driveways and steps away from the lake. Welcome to this lovely home in the Hamlet of Atherley, ide
31 Photos
Last Updated : 4 Days ago
471 Oxbow Crescent, Simcoe, ON , MLS #S13739912 , Image - 1

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471 Oxbow Crescent Collingwood, Simcoe, ON MLS® S13739912

Residential Condo & Other (Condo Townhouse)

$549000.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Stunning 3 bedroom, 2 bathroom townhouse located in a very quiet neighbourhood within the popular Living Stone Resort (formerly Cranberry Resort). Mo
Open House : Sat Sep 26, 12:00 PM to 02:00 PM
1 Photos
Last Updated : 4 Days ago
26 Irene Drive, Simcoe, ON
26 Irene Drive Painswick South, Barrie, Simcoe, ON MLS® S13497990

Residential Freehold (Detached)

$749900.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 26 Irene Drive, a fully detached home located in Barrie's desirable Painswick South neighbourhood, known for its family-friendly streets an
46 Photos
Last Updated : 4 Days ago
309 Beech Street, Simcoe, ON , MLS #S13754354 , Image - 1

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309 Beech Street Collingwood, Simcoe, ON MLS® S13754354

Residential Freehold (Detached)

$929000.0
  • 4 Beds
  • 2 Baths
  • 2000-2500 sq-ft
A Classic Collingwood Gem on one of the Town's Coveted Tree Streets. If you've been searching for a home you can truly make your own, this is the oppo
48 Photos
Last Updated : 4 Days ago
17 Sweet Cicely Street, Simcoe, ON , MLS #S13491532 , Image - 1

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17 Sweet Cicely Street Midhurst, Springwater, Simcoe, ON MLS® S13491532

Residential Freehold (Semi-Detached )

$669000.0
price drop iconPrice drop by 10.7%
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this bright Brookfield built 3 bedrooms 3 bathrooms semi-detached home in a family friendly neighborhood. Extremely well maintained, move i
49 Photos
Last Updated : 4 Days ago
2946 92 County Road, Simcoe, ON , MLS #S13490828 , Image - 1

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2946 92 County Road Rural Springwater, Springwater, Simcoe, ON MLS® S13490828

Residential Freehold (Detached)

$1024000.0
price drop iconPrice drop by 10.9%
  • 3 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Enjoy private country living at its finest while being just minutes from all the east-end amenities of Wasaga Beach, including the state-of-the-art co
32 Photos
Last Updated : 4 Days ago
333 Sunseeker Avenue, Simcoe, ON , MLS #N13163906 , Image - 1

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Unit-303, 333 Sunseeker Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13163906

Residential Condo & Other (Common Element Condo)

$699999.0
price drop iconPrice drop by 4.1%
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
***SELLER WILL PAY 2% ENTRY FEE***Sunseeker is Friday Harbour's newest collection of marina-side luxury residences, offering boutique hotel-inspired d
50 Photos
Last Updated : 4 Days ago
89 Sovereign's Gate, Simcoe, ON , MLS #S13765570 , Image - 1

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89 Sovereign's Gate Innis-Shore, Barrie, Simcoe, ON MLS® S13765570

Residential Freehold (Detached)

$984888.0
  • 4 +2 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to 89 Sovereigns Gate, an impressive 6-bedroom family home offering approximately 2,875 sq ft above grade and over 3,600 sq ft of finished liv
40 Photos
Last Updated : 4 Days ago
3400 Baldwick Lane, Simcoe, ON , MLS #S13801498 , Image - 1

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3400 Baldwick Lane Rural Springwater, Springwater, Simcoe, ON MLS® S13801498

Residential Freehold (Detached)

$1489000.0
  • 10 Beds
  • 7 Baths
  • 5000 + sq-ft
Top 5 Reasons You Will Love This Home: 1) Discover an extraordinary 50+ acre country retreat less than 10 minutes from Barrie, offering over 1,000' of
20 Photos
Last Updated : 4 Days ago
29 Shelley Lane, Simcoe, ON , MLS #S13811238 , Image - 1

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29 Shelley Lane Letitia Heights, Barrie, Simcoe, ON MLS® S13811238

Residential Freehold (Detached)

$629900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
EXTENSIVELY UPDATED BACKSPLIT WITH A RENOVATED INTERIOR & A BACKYARD READY FOR LONG SUMMER NIGHTS! Major improvements include a renovated kitchen, lux
45 Photos
Last Updated : 4 Days ago
121 Lefaive Road, Simcoe, ON , MLS #S13799086 , Image - 1

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121 Lefaive Road Rural Tiny, Tiny, Simcoe, ON MLS® S13799086

Residential Freehold (Detached)

$724900.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Pan-Abode. Cawaja Beach. Four-Season Living. Welcome to 121 Lefaive Road, where cottage character, thoughtful style and the Georgian Bay lifestyle com
48 Photos
Last Updated : 4 Days ago
18 Thomas Drive, Simcoe, ON , MLS #S13811204 , Image - 1

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18 Thomas Drive Collingwood, Simcoe, ON MLS® S13811204

Residential Freehold (Att/Row/Townhouse)

$799999.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Golf course views and turnkey living meet in the heart of Mair Mills. This end-unit freehold townhome offers rare privacy, backing seamlessly onto the
21 Photos
Last Updated : 4 Days ago
185 Dunlop Street E, Simcoe, ON , MLS #S13791952 , Image - 1

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Unit-305, 185 Dunlop Street E Lakeshore, Barrie, Simcoe, ON MLS® S13791952

Residential Condo & Other (Condo Apartment)

$889000.0
  • 1 +1 Beds
  • 2 Baths
  • 800-899 sq-ft
NEVER-LIVED-IN LUXURY WATERFRONT CONDO WITH KEMPENFELT BAY VIEWS, EXTENSIVE UPGRADES, AN ALL-SEASON LUMON BALCONY & PREMIUM AMENITIES! Set directly on
Open House : Sat Sep 26, 10:00 AM to 12:00 PM
39 Photos
Last Updated : 4 Days ago
17 Bridle Path, Simcoe, ON , MLS #S13811192 , Image - 1

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17 Bridle Path Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13811192

Residential Freehold (Detached)

$1239999.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this stunning log-style chalet nestled in the heart of Horseshoe Valley, Oro-Medonte - one of Ontario's most sought-after four-season commu
Open House : Sat Oct 03, 12:00 PM to 02:00 PM
31 Photos
Last Updated : 4 Days ago
390 Mildred Street, Simcoe, ON , MLS #S13811184 , Image - 1

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390 Mildred Street Midland, Simcoe, ON MLS® S13811184

Residential Freehold (Detached)

$349900.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Step inside and discover a home with plenty of space to make your own, where generously sized principal room
26 Photos
Last Updated : 4 Days ago
39 Naylor Drive, Simcoe, ON , MLS #N13733958 , Image - 1

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39 Naylor Drive Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13733958

Residential Freehold (Detached)

$899000.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Opportunity awaits!! The Eldon model By Lormel Homes Approx 1,900Sqft Features an open concept layout offering 4 bedrooms & 3 full baths on the second
25 Photos
Last Updated : 4 Days ago
81 Laguna Parkway, Simcoe, ON , MLS #S13709362 , Image - 1

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Unit-7, 81 Laguna Parkway Rural Ramara, Ramara, Simcoe, ON MLS® S13709362

Residential Condo & Other (Condo Townhouse)

$319000.0
  • 2 Beds
  • 3 Baths
  • 1000-1199 sq-ft
Discover the charm of waterfront living in this unique 2-bedroom condo townhouse in the heart of Lagoon City. Offering a bright and inviting layout, t
46 Photos
Last Updated : 4 Days ago
487 Tiny Beaches Road S, Simcoe, ON , MLS #S13811082 , Image - 1

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487 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13811082

Residential Freehold (Detached)

$699900.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Live just moments from the sparkling shores of Georgian Bay. Set in a prime location across from the water, this 3-bedroom, 2-bathroom home is just a
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