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Houses for Sale in Simcoe Under $500K - P18

Showing results 511 - 540 of 1116
Last Updated: September 28, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
28 Photos
Last Updated : 23 Days ago
68 Tiny Beaches Road S, Simcoe, ON , MLS #S13745562 , Image - 1
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68 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13745562

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
If you are looking for a simple cottage offering a private setting and postcard perfect views then you've just found it. This three bedroom cottage is
49 Photos
Last Updated : 23 Days ago
23 Dawson Drive, Simcoe, ON , MLS #S13138956 , Image - 1

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Unit-98, 23 Dawson Drive Collingwood, Simcoe, ON MLS® S13138956

Residential Condo & Other (Condo Apartment)

$399000.0
price drop iconPrice drop by 11.1%
  • 2 Beds
  • 2 Baths
  • 700-799 sq-ft
Welcome to this Lovely Ground Floor Condo tucked away in Secluded Setting along 23 Dawson Drive, Unit # 98. The Private Patio is set up perfectly for
25 Photos
Last Updated : 23 Days ago
5 Murray Drive, Simcoe, ON , MLS #S13744832 , Image - 1

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5 Murray Drive Wasaga Beach, Simcoe, ON MLS® S13744832

Residential Freehold (Modular Home)

$249000.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Resort-Style Retirement Living - Look No Further! Welcome to this charming 2-bedroom, 2-bathroom bungalow located in a welcoming, year-round 55+ commu
27 Photos
Last Updated : 23 Days ago
375 Sea Ray Avenue, Simcoe, ON , MLS #N13687514 , Image - 1

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Unit-133, 375 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13687514

Residential Condo & Other (Condo Apartment)

$497000.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
Turn-Key & Fully Furnished at Friday Harbour Resort! Welcome to Aquarius, where effortless resort living meets modern comfort. This beautifully furnis
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
47 Photos
Last Updated : 23 Days ago
10 Cabin Crescent, Simcoe, ON , MLS #S13744104 , Image - 1

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10 Cabin Crescent Wasaga Beach, Simcoe, ON MLS® S13744104

Residential Freehold (Detached)

$429000.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
A relaxed Wasaga Beach lifestyle, lake-facing outdoor space and extensive updates come together at 10 Cabin Crescent in the extended seasonal section
28 Photos
Last Updated : 23 Days ago
379 Gloucester Street, Simcoe, ON , MLS #S13542010 , Image - 1

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379 Gloucester Street Midland, Simcoe, ON MLS® S13542010

Residential Freehold (Detached)

$274777.0
price drop iconPrice drop by 8.3%
  • 2 +0 Beds
  • 1 Baths
  • 1500-2000 sq-ft
Welcome to 379 Gloucester Street in Midland, a fantastic opportunity for first-time buyers, investors, or anyone looking for a rewarding renovation pr
27 Photos
Last Updated : 24 Days ago
65 Ellen Street, Simcoe, ON , MLS #S13743990 , Image - 1

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Unit-708, 65 Ellen Street City Centre, Barrie, Simcoe, ON MLS® S13743990

Residential Condo & Other (Condo Apartment)

$479900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to worry free living, in this beautifully renovated 2 bdr condo, corner unit, with stunning views of both Kempenfelt Bay and the City Centre.
39 Photos
Last Updated : 24 Days ago
54 Fittons Road W, Simcoe, ON , MLS #S13591736 , Image - 1

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Unit-306, 54 Fittons Road W Orillia, Simcoe, ON MLS® S13591736

Residential Condo & Other (Condo Apartment)

$295000.0
price drop iconPrice drop by 7.8%
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to effortless condo living. This well maintained 2 bedroom, 2 bath condo unit in the north ward is move in ready. Whether you're looking to d
32 Photos
Last Updated : 24 Days ago
21 Dawson Drive, Simcoe, ON , MLS #S13493492 , Image - 1

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Unit-80, 21 Dawson Drive Collingwood, Simcoe, ON MLS® S13493492

Residential Condo & Other (Condo Townhouse)

$415000.0
price drop iconPrice drop by 3.3%
  • 2 Beds
  • 2 Baths
  • 700-799 sq-ft
Welcome to Unit 80 at 21 Dawson Drive, a beautifully updated two-bedroom, two-bathroom condo designed for easy, year-round living. Thoughtful renovati
27 Photos
Last Updated : 24 Days ago
1558 Champlain Road, Simcoe, ON , MLS #S13557406 , Image - 1

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1558 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13557406

Residential Freehold (Detached)

$410000.0
price drop iconPrice drop by 6.8%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Looking for a true summer cottage escape? This three bedroom seasonal, full insulated cottage presents a fantastic opportunity to own an affordable re
41 Photos
Last Updated : 24 Days ago
5 Dawson Drive, Simcoe, ON , MLS #S13588828 , Image - 1

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Unit-314, 5 Dawson Drive Collingwood, Simcoe, ON MLS® S13588828

Residential Condo & Other (Condo Townhouse)

$430000.0
price drop iconPrice drop by 9.5%
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Rare Opportunity in Cranberry! Enjoy the convenience of ground-floor living. This spacious ground-level bungalow condo offers exceptional flexibility
28 Photos
Last Updated : 24 Days ago
13 Harbour Street W, Simcoe, ON , MLS #S13587208 , Image - 1

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Unit-253, 13 Harbour Street W Collingwood, Simcoe, ON MLS® S13587208

Residential Condo & Other (Condo Townhouse)

$329900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to 253-13 Harbour Street West. This 2-bedroom, 1-bath townhouse condo is nestled among the mature trees of Cranberry, offering a fantastic opp
40 Photos
Last Updated : 24 Days ago
5 Dawson Drive, Simcoe, ON , MLS #S13626190 , Image - 1

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Unit-305, 5 Dawson Drive Collingwood, Simcoe, ON MLS® S13626190

Residential Condo & Other (Condo Townhouse)

$449900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Beautifully renovated from top to bottom, this 2-bedroom, 1-bathroom end-unit townhouse condo is tucked among the mature trees of Cranberry and offers
6 Photos
Last Updated : 24 Days ago
Part Lot 25 (Part 2) ROBINSON Road, Simcoe, ON , MLS #S13732986 , Image - 1

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Part Lot 25 (Part 2) ROBINSON Road Wasaga Beach, Simcoe, ON MLS® S13732986

Residential Freehold (Vacant Land)

$264900.0
  • < 700 sq-ft
Discover the perfect opportunity to build your dream home or cottage on this spacious vacant lot located in the heart of Wasaga Beach. Situated in a v
6 Photos
Last Updated : 24 Days ago
315 Sunnidale Road, Simcoe, ON , MLS #S13111666 , Image - 1

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315 Sunnidale Road Wasaga Beach, Simcoe, ON MLS® S13111666

Residential Freehold (Vacant Land)

$249900.0
  • < 700 sq-ft
This 85x100 ft lot with mature trees is conveniently located in the centre of town in a mature neighbourhood and has water and sewer at the lot line.
12 Photos
Last Updated : 24 Days ago
280 Aberdeen Boulevard, Simcoe, ON , MLS #S13730886 , Image - 1

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Unit-415, 280 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13730886

Residential Condo & Other (Condo Apartment)

$399900.0
  • 2 Beds
  • 1 Baths
  • 600-699 sq-ft
Penthouse overlooking Georgian Bay, anyone? If you have ever wanted a condominium with a large balcony and water views, this may be the one for you!!
5 Photos
Last Updated : 24 Days ago
LT23 Brook Avenue, Simcoe, ON , MLS #S13742354 , Image - 1
LT23 Brook Avenue Rural Tiny, Tiny, Simcoe, ON MLS® S13742354

Residential Freehold (Vacant Land)

$299900.0
RARE 1.7-ACRE SHORELINE RESIDENTIAL LOT JUST STEPS TO GEORGIAN BAY! Build your dream coastal retreat on this exceptional, ultra-private 1.7-acre parce
25 Photos
Last Updated : 24 Days ago
336 Forest Avenue N, Simcoe, ON , MLS #S13742100 , Image - 1

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336 Forest Avenue N Orillia, Simcoe, ON MLS® S13742100

Residential Freehold (Detached)

$499000.0
  • 3 +2 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Great quiet location close to Lake Couchiching. Large 4 level side split with over 2100 square feet above grade with 3 plus 2 bedrooms. 2 decks of bac
16 Photos
Last Updated : 24 Days ago
82 Mary Street, Simcoe, ON , MLS #S13680136 , Image - 1

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82 Mary Street Creemore, Clearview, Simcoe, ON MLS® S13680136

Residential Freehold (Vacant Land)

$395000.0
Escape the city and discover your own private sanctuary along the crystal-clear waters of the Mad River. Located right in the highly sought-after vill
2 Photos
Last Updated : 24 Days ago
32 Deneb Road, Simcoe, ON , MLS #S12814974 , Image - 1
32 Deneb Road Ardagh, Barrie, Simcoe, ON MLS® S12814974

Residential Freehold (Att/Row/Townhouse)

$499000.0
price drop iconPrice drop by 13.8%
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to this well-maintained 3 Bedroom, 2.5 Bathroom Townhouse located in Barrie's desirable ARDAGH NEIGHBOURHOOD. Offering approximately 1,100-1,2
22 Photos
Last Updated : 24 Days ago
40 Corner Brook Trail, Simcoe, ON , MLS #N13741242 , Image - 1

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40 Corner Brook Trail Rural Innisfil, Innisfil, Simcoe, ON MLS® N13741242

Residential Freehold (Modular Home)

$332500.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this popular and well-maintained site-built Sandalwood II home, located in the vibrant adult community of Sandycove Acres south. The home h
28 Photos
Last Updated : 24 Days ago
17 CHIPPEWA Trail, Simcoe, ON , MLS #S12728766 , Image - 1

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17 CHIPPEWA Trail Wasaga Beach, Simcoe, ON MLS® S12728766

Residential Freehold (MobileTrailer)

$99000.0
price drop iconPrice drop by 29.2%
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Escape to your ideal summer retreat at Wasaga Countrylife Resort with this immaculate 2016 Northlander Cottager Reflection model. Available seasonally
27 Photos
Last Updated : 24 Days ago
11 Beck Boulevard, Simcoe, ON , MLS #S13741128 , Image - 1

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Unit-402, 11 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13741128

Residential Condo & Other (Condo Apartment)

$449900.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Live Above It All with an Unbeatable View! Welcome to this top-floor White Sands Condo, where every window frames stunning westerly vistas of Georgian
35 Photos
Last Updated : 24 Days ago
157 Church Street, Simcoe, ON , MLS #S13737294 , Image - 1

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Unit-15, 157 Church Street Penetanguishene, Simcoe, ON MLS® S13737294

Residential Condo & Other (Condo Townhouse)

$329900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Easy Condo Living in the Heart of Penetanguishene! Enjoy the convenience and carefree lifestyle of condo living without the maintenance of a tradition
20 Photos
Last Updated : 24 Days ago
37 Todd Lane, Simcoe, ON , MLS #S13740254 , Image - 1

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37 Todd Lane Victoria Harbour, Tay, Simcoe, ON MLS® S13740254

Residential Freehold (Vacant Land)

$199000.0
Discover the opportunity to build your dream home in the charming community of Victoria Harbour. This vacant lot, measuring just under half an acre, i
29 Photos
Last Updated : 24 Days ago
85 Chaucer Crescent, Simcoe, ON , MLS #S13740148 , Image - 1

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85 Chaucer Crescent Letitia Heights, Barrie, Simcoe, ON MLS® S13740148

Residential Freehold (Semi-Detached )

$469900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome To 85 Chaucer Crescent, A Fantastic Opportunity In A Family-Friendly West Barrie Neighbourhood! This Charming 3-Bedroom, 1-Bathroom Semi-Detac
32 Photos
Last Updated : 25 Days ago
115 Bond Street, Simcoe, ON , MLS #S13626036 , Image - 1

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Unit-Unit 201, 115 Bond Street Orillia, Simcoe, ON MLS® S13626036

Residential Condo & Other (Condo Apartment)

$315000.0
price drop iconPrice drop by 3.1%
  • 2 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Welcome to this Well-Maintained Condominium Complex offering comfort, convenience, and easy living. This spacious Two-Bedroom Corner Unit features a d
5 Photos
Last Updated : 25 Days ago
117 Colborne Street E, Simcoe, ON , MLS #S13737780 , Image - 1
117 Colborne Street E Orillia, Simcoe, ON MLS® S13737780

Residential Freehold (Vacant Land)

$260000.0
Exceptional opportunity to secure a vacant parcel in the heart of Orillia. Located at 117 Colborne Street E, this property offers an exciting opportun
40 Photos
Last Updated : 25 Days ago
275 Huron Street, Simcoe, ON , MLS #S13017460 , Image - 1

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Unit-23, 275 Huron Street Stayner, Clearview, Simcoe, ON MLS® S13017460

Residential Freehold (Att/Row/Townhouse)

$499000.0
price drop iconPrice drop by 13.2%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Discover the charm of Huron Meadows, an inviting Adult Life Lease community, offering 58 units, where every detail is designed with your comfort in mi
35 Photos
Last Updated : 25 Days ago
81 Laguna Parkway, Simcoe, ON , MLS #S12867712 , Image - 1

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Unit-14, 81 Laguna Parkway Brechin, Ramara, Simcoe, ON MLS® S12867712

Residential Condo & Other (Condo Townhouse)

$424900.0
price drop iconPrice drop by 7.4%
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Discover this beautifully renovated Rarely offered end-unit 2-bedroom, 2-bath waterfront townhome in the heart of Lagoon City, perfectly situated on t
Shortlisted Properties
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