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Houses for Sale in Simcoe Under $5 Million - P33

Showing results 961 - 990 of 1054
Last Updated: May 13, 2026
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40 Photos
Last Updated : 92 Days ago
301 Sea Ray Avenue, Simcoe, ON , MLS #N12776464 , Image - 1
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Unit-C305, 301 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12776464

Residential Condo & Other (Condo Apartment)

$460000.0
  • 2 Beds
  • 2 Baths
  • 700-799 sq-ft
RESORT LIVING AT FRIDAY HARBOUR FAMILY-FRIENDLY & INVESTOR-SAVVY! Welcome to 301 Sea Ray Ave, where convenience meets ease in the heart of Friday Harb
5 Photos
Last Updated : 92 Days ago
PART 1 Ron Jones Road, Simcoe, ON , MLS #S12776204 , Image - 1
PART 1 Ron Jones Road Rural Tay, Tay, Simcoe, ON MLS® S12776204

Residential Freehold (Vacant Land)

$349900.0
Here is your opportunity to be the proud owner of this one plus acre property to build your dream home and enjoy the beauty of the rural Tay area. Pre
4 Photos
Last Updated : 92 Days ago
PART 2 Ron Jones Road, Simcoe, ON , MLS #S12776150 , Image - 1
PART 2 Ron Jones Road Rural Tay, Tay, Simcoe, ON MLS® S12776150

Residential Freehold (Vacant Land)

$349900.0
Here is your opportunity to be the proud owner of this one plus acre property to build your dream home and enjoy the beauty of the rural Tay area. Pre
10 Photos
Last Updated : 93 Days ago
17 Private Drive, Simcoe, ON , MLS #N12626674 , Image - 1

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17 Private Drive Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12626674

Residential Freehold (Detached)

$288000.0
  • < 700 sq-ft
Rare Waterfront Opportunity On The Holland River! This 50 X 100 Ft Property Is Accessed Via A Private Road With Direct Access To Yonge St Offering A P
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
22 Photos
Last Updated : 93 Days ago
185 Shephard Avenue, Simcoe, ON , MLS #N12770630 , Image - 1

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185 Shephard Avenue Alliston, New Tecumseth, Simcoe, ON MLS® N12770630

Residential Freehold (Detached)

$1089000.0
  • 4 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this beautifully upgraded home in a highly coveted location. Offering four generously sized bedrooms and four bathrooms, this exceptional p
50 Photos
Last Updated : 95 Days ago
7 Golfview Boulevard, Simcoe, ON , MLS #N12768692 , Image - 1

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7 Golfview Boulevard Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12768692

Residential Freehold (Detached)

$1749000.0
  • 3 +1 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Set on an impressive 0.75-acre lot in the prestigious Golfview Estates, this exceptional home offers the rar
13 Photos
Last Updated : 95 Days ago
250 Kingfisher Avenue, Simcoe, ON , MLS #S12654300 , Image - 1

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250 Kingfisher Avenue Port McNicoll, Tay, Simcoe, ON MLS® S12654300

Residential Freehold (Detached)

$299900.0
price drop iconPrice drop by 14.1%
  • 700-1100 sq-ft
You've just arrived in Paradise Point! This Seasonal cottage sits on a 60' x 146' lot in the heart of this beloved community. Potential !!! Project to
35 Photos
Last Updated : 96 Days ago
1961 McNeil Street, Simcoe, ON , MLS #N12718944 , Image - 1

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1961 McNeil Street Alcona, Innisfil, Simcoe, ON MLS® N12718944

Residential Freehold (Detached)

$799900.0
price drop iconPrice drop by 1.2%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Large 4 Bedroom detached, *2201* Square feet above grade as per MPAC, 9 foot ceilings main floor. Beautiful kitchen. Custom interlock front walk way a
43 Photos
Last Updated : 96 Days ago
4806 5th Side Road, Simcoe, ON , MLS #N12736340 , Image - 1

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4806 5th Side Road Rural Essa, Essa, Simcoe, ON MLS® N12736340

Residential Freehold (Detached)

$829000.0
  • 3 +1 Beds
  • 4 Baths
  • 1100-1500 sq-ft
Escape to the Country! This beautiful 2-story detached home in the highly sought-after Rural Essa community offers nearly 2,000 sq. ft. of finished li
36 Photos
Last Updated : 97 Days ago
16 Rowe Street, Simcoe, ON , MLS #N12692428 , Image - 1

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16 Rowe Street Bond Head, Bradford West Gwillimbury, Simcoe, ON MLS® N12692428

Residential Freehold (Detached)

$1181400.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Brand New Greenwood model by Sundance Homes with full Tarion Warranty. Smooth ceilings, stone countertops, and hard surface flooring throughout. Spaci
3 Photos
Last Updated : 97 Days ago
Lot 95A Reynolds Drive, Simcoe, ON , MLS #S12393577 , Image - 1
Lot 95A Reynolds Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12393577

Residential Freehold (Detached)

$539900.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome To Lakepoint Village's Land Leased Community Located Just Outside Of Orillia With All The Amenities You Need! This Home Offers Elegant Main Fl
13 Photos
Last Updated : 98 Days ago
1277 Sunnidale Road, Simcoe, ON , MLS #S12759654 , Image - 1

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1277 Sunnidale Road Rural Springwater, Springwater, Simcoe, ON MLS® S12759654

Residential Freehold (Detached)

$1450000.0
  • 4 +2 Beds
  • 5 Baths
  • 2000-2500 sq-ft
Welcome to this one-of-a-kind custom-built side split home, perfectly situated on a spacious 120x193ft lot. Designed with versatility in mind, this pr
14 Photos
Last Updated : 98 Days ago
15 Huron Circle, Simcoe, ON , MLS #S12702652 , Image - 1

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15 Huron Circle Wasaga Beach, Simcoe, ON MLS® S12702652

Residential Freehold (MobileTrailer)

$110000.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Seasonal retreat in popular Countrylife Resort. (7 months April 26th-Nov 16th). Short walk to the Beach! Immaculately maintained 2004 Quailridge featu
22 Photos
Last Updated : 98 Days ago
6509 13th Line N/A, Simcoe, ON , MLS #N12748140 , Image - 1

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6509 13th Line N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12748140

Residential Freehold (Detached)

$1695000.0
  • 9 Beds
  • 7 Baths
  • 1500-2000 sq-ft
Welcome to your Private Countryside Estate overlooking Alliston !Scenic Ranch style home on 10 acres with river frontage & bonus beach area including
5 Photos
Last Updated : 99 Days ago
712 Mt St Louis Road W, Simcoe, ON , MLS #S12755424 , Image - 1
Unit-Part 1, 712 Mt St Louis Road W Moonstone, Oro-Medonte, Simcoe, ON MLS® S12755424

Residential Freehold (Vacant Land)

$449000.0
  • < 700 sq-ft
Beautiful building lot. Border of trees around the property for privacy. Almost 1 Acre of sandy soil, great soil to build on. Services required natura
11 Photos
Last Updated : 99 Days ago
LT 4 Glenn Howard Court, Simcoe, ON , MLS #S12752318 , Image - 1

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LT 4 Glenn Howard Court Rural Tiny, Tiny, Simcoe, ON MLS® S12752318

Residential Freehold (Vacant Land)

$399900.0
  • < 700 sq-ft
Top 5 Reasons You Will Love This Property: 1) Rare opportunity to own one of the last remaining lots in the prestigious Copeland Creek estate communit
1 Photos
Last Updated : 100 Days ago
1000 Strawberry Island, Simcoe, ON
1000 Strawberry Island Rural Ramara, Ramara, Simcoe, ON MLS® S12751218

Residential Freehold (Other)

$4290000.0
  • < 700 sq-ft
A Truly Exceptional Fall And Winter Opportunity To Own Strawberry Island-A 26-Acre Private, Iconic, And Historically Significant Sanctuary On Lake Sim
44 Photos
Last Updated : 100 Days ago
2240 South Orr Lake Road, Simcoe, ON , MLS #S12750724 , Image - 1

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2240 South Orr Lake Road Rural Springwater, Springwater, Simcoe, ON MLS® S12750724

Residential Freehold (Detached)

$1600000.0
  • 3 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Experience refined waterfront living at this exceptional retreat on South Orr Lake. Thoughtfully designed to blend elegance, comfort, and natural beau
25 Photos
Last Updated : 100 Days ago
5984 3rd Line, Simcoe, ON , MLS #N12749918 , Image - 1

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5984 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12749918

Residential Freehold (Detached)

$2949000.0
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 5984 3rd Line This sprawling property boasts a charming 4 bedroom, 2 bathroom home situated on 45 acres of picturesque farmland 25 acres cu
49 Photos
Last Updated : 101 Days ago
69 CITYVIEW Circle, Simcoe, ON , MLS #S12746916 , Image - 1

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69 CITYVIEW Circle Holly, Barrie, Simcoe, ON MLS® S12746916

Residential Freehold (Detached)

$1550000.0
  • 5 +0 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Discover this beautifully maintained home on a rare pie-shaped lot backing directly onto Ardagh Forest, offering unparalleled privacy and a peaceful,
37 Photos
Last Updated : 103 Days ago
49 Burns Circle, Simcoe, ON , MLS #S12742706 , Image - 1

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49 Burns Circle Letitia Heights, Barrie, Simcoe, ON MLS® S12742706

Residential Freehold (Link)

$580000.0
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 49 Burns Circle, a fantastic opportunity in sought-after Northwest Barrie. This bright and well-maintained end-unit link home is attached b
2 Photos
Last Updated : 103 Days ago
379 ROPE Boulevard, Simcoe, ON , MLS #S12741538 , Image - 1
379 ROPE Boulevard Rural Tay, Tay, Simcoe, ON MLS® S12741538

Residential Freehold (Vacant Land)

$349900.0
  • < 700 sq-ft
Discover the perfect blend of nature and convenience with this stunning 3+ acre vacant land property in Waubaushene. Nestled in a serene rural setting
35 Photos
Last Updated : 104 Days ago
1165 Mitchell Court, Simcoe, ON , MLS #N12739190 , Image - 1

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1165 Mitchell Court Alcona, Innisfil, Simcoe, ON MLS® N12739190

Residential Freehold (Detached)

$1099000.0
  • 2 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
This Income Generating Home Has Luxury Self Contained Apartment Generating $2000 Rent Plus Additional Space Room. 3800 Sqft Of Living Space, 1900 Sq.
11 Photos
Last Updated : 105 Days ago
7012 County Road 169 N/A, Simcoe, ON , MLS #S12647880 , Image - 1

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7012 County Road 169 N/A Rural Ramara, Ramara, Simcoe, ON MLS® S12647880

Residential Freehold (Vacant Land)

$349000.0
  • < 700 sq-ft
5-ACRE WATERFRONT RETREAT ALONG THE BLACK RIVER - ENDLESS POTENTIAL AWAITS! Discover the ultimate opportunity to create your dream retreat on this pea
38 Photos
Last Updated : 105 Days ago
10 12 Line N, Simcoe, ON , MLS #S12106183 , Image - 1

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10 12 Line N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S12106183

Residential Freehold (Vacant Land)

$1539900.0
  • 5 Beds
  • 2 Baths
  • < 700 sq-ft
93.47 acres of farmland with amazing visual exposure of 1,555 feet right on busy Highway 11 perfectly positioned between Barrie and Orillia making thi
5 Photos
Last Updated : 106 Days ago
7046 Sideroad 30/31 Nottawasaga N/A, Simcoe, ON , MLS #S12475928 , Image - 1
7046 Sideroad 30/31 Nottawasaga N/A Stayner, Clearview, Simcoe, ON MLS® S12475928

Residential Freehold (Vacant Land)

$369900.0
Top 5 Reasons You Will Love This Property: 1) Discover the tranquility of country living on this peaceful 1.6-acre vacant lot, your chance to embrace
24 Photos
Last Updated : 107 Days ago
11 Knox Road E, Simcoe, ON , MLS #S12604540 , Image - 1

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11 Knox Road E Wasaga Beach, Simcoe, ON MLS® S12604540

Residential Freehold (Vacant Land)

$499900.0
price drop iconPrice drop by 9.1%
Nestled at the bow of the Nottawasaga River, this parcel of land is a true gem waiting to be discovered. Offering over 2 acres of landscape, it boasts
1 Photos
Last Updated : 112 Days ago
383 Champlain Road, Simcoe, ON
383 Champlain Road Penetanguishene, Simcoe, ON MLS® S12357426

Residential Freehold (Detached)

$1049000.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Century Cottage with Endless Potential! Waterfront on Penetang Bay! Bring your vision and make this charming 2-storey century cottage your dream water
39 Photos
Last Updated : 113 Days ago
61 Tracey Lane, Simcoe, ON , MLS #S12655776 , Image - 1

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61 Tracey Lane Collingwood, Simcoe, ON MLS® S12655776

Residential Freehold (Detached)

$799900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to Indigo Estates, Collingwood's new premier community. 61Tracey La , 1978 Sq Ft , 4 Bedrooms and 3 Bathrooms with main floor office.Collingwo
21 Photos
Last Updated : 113 Days ago
9 Harbour Street E, Simcoe, ON , MLS #S11931442 , Image - 1

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9 Harbour Street E
Unit-4109-41, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S11931442

Residential Condo & Other (Timeshare)

$40000.0
price drop iconPrice drop by 33.3%
  • 2 Beds
  • 2 Baths
  • 0-499 sq-ft
3 WEEK FRACTIONAL OWNERSHIP AT Collingwood's only waterfront resort. Located on the 4th floor of Living Water Resort, this unit offers amazing views o
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