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Houses for Sale in Simcoe Under $5 Million - P43

Showing results 1261 - 1290 of 5140
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)
35 Photos
Last Updated : 6 Days ago
238 King Street S, Simcoe, ON , MLS #N13642158 , Image - 1
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238 King Street S Alliston, New Tecumseth, Simcoe, ON MLS® N13642158

Residential Freehold (Detached)

$799999.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to this Exquisite home! Fully finished up & down this home is open concept, great for entertaining. Hardwood floors through out the whole hous
38 Photos
Last Updated : 6 Days ago
6 John James Drive, Simcoe, ON , MLS #N13607588 , Image - 1

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6 John James Drive Angus, Essa, Simcoe, ON MLS® N13607588

Residential Freehold (Detached)

$765000.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Terrifically maintained, all brick, raised bungalow with incredible curb appeal. The appeal doesn't stop at the curb either, the entire lot has been t
48 Photos
Last Updated : 6 Days ago
48 Ruffet Drive, Simcoe, ON , MLS #S13570364 , Image - 1

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48 Ruffet Drive Edgehill Drive, Barrie, Simcoe, ON MLS® S13570364

Residential Freehold (Detached)

$760000.0
price drop iconPrice drop by 2.6%
  • 2 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
In this market, homes with true pride of ownership are rare. This raised bungalow in Barrie's west end has been loved and maintained by the same owner
50 Photos
Last Updated : 6 Days ago
320 6 Concession E, Simcoe, ON , MLS #S13608480 , Image - 1

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320 6 Concession E Rural Tiny, Tiny, Simcoe, ON MLS® S13608480

Residential Freehold (Detached)

$1399900.0
  • 6 Beds
  • 4 Baths
  • 2500-3000 sq-ft
From the moment you arrive, this exceptional 25-acre country estate welcomes you with professionally landscaped perennial gardens, mature trees, and a
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
50 Photos
Last Updated : 6 Days ago
11 Nevis Ridge Drive, Simcoe, ON , MLS #S13207526 , Image - 1

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11 Nevis Ridge Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13207526

Residential Freehold (Detached)

$2100000.0
  • 3 +3 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Eleven Nevis Ridge is a rare Scandinavian scribe Western red cedar log home - a hand-fitted, one-of-a-kind retreat tucked at the end of a quiet cul-de
41 Photos
Last Updated : 6 Days ago
78 Zima Crescent, Simcoe, ON , MLS #N13615992 , Image - 1

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78 Zima Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13615992

Residential Freehold (Link)

$659000.0
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Opportunity Knocks! Beautiful home with a Legal 2-bedroom retrofitted walk-out basement apartment registered with Bradford West Gwillimbury. Fantastic
36 Photos
Last Updated : 6 Days ago
195 Ridge Way, Simcoe, ON , MLS #N13447364 , Image - 1

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195 Ridge Way Alliston, New Tecumseth, Simcoe, ON MLS® N13447364

Residential Condo & Other (Detached Condo)

$1238000.0
  • 2 +1 Beds
  • 3 Baths
  • 1400-1599 sq-ft
Look No Further, Stunning Open Concept Tastefully Renovated Bungalow With Breathtaking View Of The Golf Course Located in the Virtually Maintenance F
47 Photos
Last Updated : 6 Days ago
91 Simcoe Road, Simcoe, ON , MLS #S13489278 , Image - 1

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91 Simcoe Road Brechin, Ramara, Simcoe, ON MLS® S13489278

Residential Freehold (Detached)

$580000.0
price drop iconPrice drop by 21.5%
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
91 Simcoe Road offers something uncommon in Lagoon City: a 98 x 270 ft lot. Room between you and the neighbours, a deep back yard, and parking for up
25 Photos
Last Updated : 6 Days ago
208 Diana Drive, Simcoe, ON , MLS #S13508460 , Image - 1

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208 Diana Drive Orillia, Simcoe, ON MLS® S13508460

Residential Freehold (Detached)

$699999.0
price drop iconPrice drop by 6.5%
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 208 Diana Drive, located in Orillia's highly sought-after Westridge community. This beautifully maintained home has been thoughtfully renov
19 Photos
Last Updated : 6 Days ago
16 William Street, Simcoe, ON , MLS #S13588234 , Image - 1

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16 William Street Orillia, Simcoe, ON MLS® S13588234

Residential Freehold (Detached)

$499900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
CENTURY CHARM & THOUGHTFUL UPDATES IN A CENTRAL ORILLIA LOCATION! This is the house with the storybook front porch, the greenery-filled backyard with
44 Photos
Last Updated : 6 Days ago
163 Woodland Drive, Simcoe, ON , MLS #S13578644 , Image - 1

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163 Woodland Drive Midland, Simcoe, ON MLS® S13578644

Residential Freehold (Detached)

$689000.0
price drop iconPrice drop by 0.9%
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Stunning Fully Updated Family Home in Midland's Prestigious West End. Welcome to this exceptional, move-in-ready family home, ideally located in one o
44 Photos
Last Updated : 6 Days ago
1787 Champlain Road, Simcoe, ON , MLS #S13641804 , Image - 1

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1787 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13641804

Residential Freehold (Detached)

$1199900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Experience the ultimate waterfront lifestyle with 107' of pristine sandy shoreline, offering a clean, shallo
49 Photos
Last Updated : 6 Days ago
145 Milby Crescent, Simcoe, ON , MLS #N13584250 , Image - 1

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145 Milby Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13584250

Residential Freehold (Detached)

$1180000.0
  • 4 +1 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this stunning 4-bedroom detached home offering over 3,300 sq. ft. of beautifully designed living space in one of Bradford's most desirable
49 Photos
Last Updated : 6 Days ago
1650 Trader Cowan Road, Simcoe, ON , MLS #S13629486 , Image - 1

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1650 Trader Cowan Road Rural Severn, Severn, Simcoe, ON MLS® S13629486

Residential Freehold (Detached)

$975000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this custom built duplex bungalow in the peaceful countryside of Severn on a paved road, offering exceptional flexibility for families, ext
35 Photos
Last Updated : 6 Days ago
1720 Tay Point Road, Simcoe, ON , MLS #S13641704 , Image - 1

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1720 Tay Point Road Penetanguishene, Simcoe, ON MLS® S13641704

Residential Freehold (Detached)

$699000.0
  • 3 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Fully rebuilt in 2019, this stunning 4-season home or cottage perfectly delivers modern upgrades with timele
36 Photos
Last Updated : 6 Days ago
2234 Crystal Beach Road, Simcoe, ON , MLS #N13631286 , Image - 1

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2234 Crystal Beach Road Alcona, Innisfil, Simcoe, ON MLS® N13631286

Residential Freehold (Detached)

$549999.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Looking for Lake Simcoe views from your front deck without paying the price and maintenance of a waterfront property? Then 2234 Crystal Beach Road is
30 Photos
Last Updated : 6 Days ago
204 Cox Mill Road, Simcoe, ON , MLS #S13641650 , Image - 1

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204 Cox Mill Road Painswick North, Barrie, Simcoe, ON MLS® S13641650

Residential Freehold (Detached)

$565000.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Top 5 Reasons You Will Love This Home: 1) Beautifully updated bungalow set on an impressive 200' deep lot in one of Barrie's most sought-after neighbo
50 Photos
Last Updated : 6 Days ago
8 Elderberry Way, Simcoe, ON , MLS #N13639432 , Image - 1

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8 Elderberry Way Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N13639432

Residential Freehold (Detached)

$1499900.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
8 Elderberry Way showcases an exceptional 3600 sq. ft. detached residence in the prestigious Colgan Crossing community of Tottenham, set on an expansi
45 Photos
Last Updated : 6 Days ago
60 MUSEUM Drive, Simcoe, ON , MLS #S13573110 , Image - 1

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Unit-505, 60 MUSEUM Drive Orillia, Simcoe, ON MLS® S13573110

Residential Condo & Other (Condo Townhouse)

$779000.0
  • 2 Beds
  • 3 Baths
  • 1800-1999 sq-ft
Welcome to this immaculate bungaloft end-unit condominium in the sought-after Leacock Village, where comfort, style, and an exceptional location come
21 Photos
Last Updated : 6 Days ago
375 Sea Ray Avenue, Simcoe, ON , MLS #N13435058 , Image - 1

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Unit-110, 375 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13435058

Residential Condo & Other (Condo Apartment)

$439000.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
Premium ground floor *Fully furnished (optional) CORNER unit*! Extra large space! Rare floorplan with open concept living/kitchen with windows all aro
21 Photos
Last Updated : 6 Days ago
38 Bellehumeur Road, Simcoe, ON , MLS #S13607418 , Image - 1

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38 Bellehumeur Road Rural Tiny, Tiny, Simcoe, ON MLS® S13607418

Residential Freehold (Detached)

$799999.0
price drop iconPrice drop by 2.4%
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this brand new bungalow offering the ease and simplicity of main floor living. Everything you need is on one level, making it an ideal fit
25 Photos
Last Updated : 6 Days ago
28 Britannia Avenue, Simcoe, ON , MLS #N13594120 , Image - 1

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28 Britannia Avenue Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13594120

Residential Freehold (Detached)

$699900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
3 Bedroom Level-4 Sidesplit Nestled On Incredibly Private 55 x 123Ft Lot Surrounded By Mature Trees & Beautiful Perennial Gardens In The Heart Of Brad
36 Photos
Last Updated : 6 Days ago
1537 Harker Street, Simcoe, ON , MLS #N13641390 , Image - 1

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1537 Harker Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13641390

Residential Freehold (Detached)

$799000.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
WELCOME TO THIS STUNNING 3-YEAR-OLD EXECUTIVE HOME LOCATED IN ONE OF INNISFIL'S MOST DESIRABLEAND FAMILY-FRIENDLY COMMUNITIES, JUST MINUTES FROM THE L
20 Photos
Last Updated : 6 Days ago
7 Michelle Drive, Simcoe, ON , MLS #S13527900 , Image - 1

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7 Michelle Drive Painswick South, Barrie, Simcoe, ON MLS® S13527900

Residential Freehold (Detached)

$799900.0
price drop iconPrice drop by 5.8%
  • 4 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Ideally located close to parks, golf courses, shopping, dining, schools, and quick Highway 400 access, this property also places you just a short driv
15 Photos
Last Updated : 6 Days ago
1419 Port Stanton Parkway, Simcoe, ON , MLS #S12924416 , Image - 1

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1419 Port Stanton Parkway Rural Severn, Severn, Simcoe, ON MLS® S12924416

Residential Freehold (Vacant Land)

$699000.0
price drop iconPrice drop by 9.8%
A Unique Waterfront Property located in the Quaint Lakeside Hamlet of Port Stanton. Build your own Cottage or Home with beautiful views of Sparrow Lak
36 Photos
Last Updated : 6 Days ago
3413 FLAT RAPIDS Lane, Simcoe, ON , MLS #S13411492 , Image - 1

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3413 FLAT RAPIDS Lane Rural Severn, Severn, Simcoe, ON MLS® S13411492

Residential Freehold (Detached)

$1775000.0
price drop iconPrice drop by 2.7%
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Deep water. Five private acres. Direct access to the Trent-Severn Waterway. Some waterfront is for looking at - this is waterfront you live on. Tucked
34 Photos
Last Updated : 6 Days ago
84 Clapperton Street, Simcoe, ON , MLS #S13049950 , Image - 1

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84 Clapperton Street Codrington, Barrie, Simcoe, ON MLS® S13049950

Residential Freehold (Att/Row/Townhouse)

$799900.0
  • 3 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Distinguished Freehold Townhome From Acclaimed Builder Daycor. Built in 2019, This Executive Residence Showcases Approximately 2,400+ Sq. Ft. Above Gr
26 Photos
Last Updated : 6 Days ago
104 Eccles Street N, Simcoe, ON , MLS #S13570318 , Image - 1

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104 Eccles Street N Queen's Park, Barrie, Simcoe, ON MLS® S13570318

Residential Freehold (Detached)

$599000.0
price drop iconPrice drop by 4.9%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to this spacious 1,700+ sq. ft. home, tucked away on a quiet dead-end street where peace, privacy, and nature come together. Backing onto envi
17 Photos
Last Updated : 6 Days ago
13 Huron Circle, Simcoe, ON , MLS #S13641194 , Image - 1

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13 Huron Circle Wasaga Beach, Simcoe, ON MLS® S13641194

Residential Freehold (MobileTrailer)

$104900.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
FULLY FURNISHED SEASONAL RETREAT BACKING ONTO A QUIET POND WITH ENDLESS RESORT AMENITIES! Move-in ready and backing onto a quiet pond with no direct r
3 Photos
Last Updated : 6 Days ago
196 Burton Avenue, Simcoe, ON , MLS #S13641188 , Image - 1
196 Burton Avenue Allandale, Barrie, Simcoe, ON MLS® S13641188

Residential Freehold (Vacant Land)

$1275000.0
  • 5000 + sq-ft
***Extraordinary Opportunity For Investors!*** This Property Is Already Zoned For A Mixed Residential Commercial/Use. 6 Townhouses With 6 Commercial U
Shortlisted Properties
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