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Houses for Sale in Simcoe Under $500K - P20

Showing results 571 - 600 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)
47 Photos
Last Updated : 27 Days ago
794097 124 Grey Road, Simcoe, ON , MLS #S13715586 , Image - 1
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794097 124 Grey Road Singhampton, Clearview, Simcoe, ON MLS® S13715586

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to this beautifully upgraded home in the heart of Singhampton, where convenience meets four-season outdoor adventure. This 3-bedroom, 2-bathro
50 Photos
Last Updated : 27 Days ago
30 Mulligan Lane, Simcoe, ON , MLS #S13629740 , Image - 1

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Unit-8, 30 Mulligan Lane Wasaga Beach, Simcoe, ON MLS® S13629740

Residential Condo & Other (Condo Apartment)

$349900.0
price drop iconPrice drop by 2.8%
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Spacious 2-Bedroom Condo with Oversized Screened-In Balcony in Marlwood Golf Course Community! The bright open-concept layout features a kitchen with
29 Photos
Last Updated : 27 Days ago
24 Poplar Drive, Simcoe, ON , MLS #S13478192 , Image - 1

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24 Poplar Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13478192

Residential Freehold (Detached)

$419900.0
price drop iconPrice drop by 2.3%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Discover the timeless charm of Georgian Bay year round cottage living! This classic 3-bedroom cottage offers the perfect family retreat, with deeded a
21 Photos
Last Updated : 27 Days ago
415 Sea Ray Avenue, Simcoe, ON , MLS #N13231434 , Image - 1

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Unit-224, 415 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13231434

Residential Condo & Other (Condo Apartment)

$399000.0
  • 1 Beds
  • 1 Baths
  • 500-599 sq-ft
Resort Living at It's Finest FURNISHED FULLY UPGRADED West facing VIEWS OF THE POOL & HOT TUB 1 Bedroom Suite At Friday Harbour Waterfront Four Season
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
4 Photos
Last Updated : 27 Days ago
2889 Sunset Drive, Simcoe, ON , MLS #S13476574 , Image - 1
2889 Sunset Drive Brechin, Ramara, Simcoe, ON MLS® S13476574

Residential Freehold (Vacant Land)

$169000.0
price drop iconPrice drop by 15.1%
Rare opportunity to own a clean, vacant building lot just steps from beautiful Lake Simcoe. Featuring an impressive 90 ft frontage x 200 ft depth, thi
1 Photos
Last Updated : 27 Days ago
36 Southview Dr R.R.#3, Brechin Drive S, Simcoe, ON
36 Southview Dr R.R.#3, Brechin Drive S Brechin, Ramara, Simcoe, ON MLS® S13601302

Residential Freehold (Vacant Land)

$299000.0
This rare vacant lot is ready for your dream home! 100 x 200 dry building lot on a pond sits on a quiet street in Bayshore Village. Amenities galore!
5 Photos
Last Updated : 27 Days ago
6 Tioga Boulevard, Simcoe, ON , MLS #N12167264 , Image - 1
6 Tioga Boulevard Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N12167264

Residential Freehold (Vacant Land)

$365000.0
price drop iconPrice drop by 26.9%
  • < 700 sq-ft
Desirable 1.75 Acre Pie-Shaped Lot In An Established Estate Lot Neighbourhood. Trees Along Rear Boundary With Level Cleared Area To Build Your Dream H
20 Photos
Last Updated : 27 Days ago
16 Westbury Road, Simcoe, ON , MLS #S13728738 , Image - 1

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Unit-202, 16 Westbury Road Wasaga Beach, Simcoe, ON MLS® S13728738

Residential Condo & Other (Condo Apartment)

$369900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Discover comfort and convenience in this bright two-bedroom, two bath condo perfectly positioned to overlook a serene, forested green space. Featuring
28 Photos
Last Updated : 27 Days ago
1 Paradise Boulevard, Simcoe, ON , MLS #S13501932 , Image - 1

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Unit-Unit 29, 1 Paradise Boulevard Rural Ramara, Ramara, Simcoe, ON MLS® S13501932

Residential Condo & Other (Condo Townhouse)

$379649.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Great Opportunity To Be A Part of a Wonderful Established Waterfront Community Located In Lagoon City On The Shores of Lake Simcoe. This Two Bedroom,
40 Photos
Last Updated : 27 Days ago
5 Spooner Crescent, Simcoe, ON , MLS #S13134708 , Image - 1

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Unit-311, 5 Spooner Crescent Collingwood, Simcoe, ON MLS® S13134708

Residential Condo & Other (Condo Apartment)

$439000.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
Welcome to #311 - 5 Spooner Crescent in the sought-after Blue Fairway community, a maintenance-free lifestyle in the heart of Collingwood. This stylis
36 Photos
Last Updated : 27 Days ago
2 Paradise Boulevard, Simcoe, ON , MLS #S13722268 , Image - 1

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Unit-Unit 19, 2 Paradise Boulevard Brechin, Ramara, Simcoe, ON MLS® S13722268

Residential Condo & Other (Condo Townhouse)

$410649.0
  • 3 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Waterfront Living in Lagoon City on Lake Simcoe is Waiting for You in this 3 Bedroom, 2 Bathroom Beautiful Condo Just Steps Away to Private Park and S
1 Photos
Last Updated : 27 Days ago
4 Paradise Boulevard, Simcoe, ON
Unit-3, 4 Paradise Boulevard Brechin, Ramara, Simcoe, ON MLS® S13682758

Residential Condo & Other (Condo Townhouse)

$410000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
This waterfront community offers a charming 2-bedroom, 1.5-bath townhome just steps from a private beach on beautiful Lake Simcoe. The open-concept ki
17 Photos
Last Updated : 27 Days ago
43 Coulter Street, Simcoe, ON , MLS #S12829808 , Image - 1

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Unit-20, 43 Coulter Street Sunnidale, Barrie, Simcoe, ON MLS® S12829808

Residential Condo & Other (Condo Apartment)

$417900.0
price drop iconPrice drop by 2.8%
  • 2 Beds
  • 1 Baths
  • 900-999 sq-ft
Welcome to Sunnidale Vistas! This large, bright 2-bedroom end-unit condo offers over 1,000 sq ft of comfortable living space with a private view and e
27 Photos
Last Updated : 27 Days ago
9 Harbour Street E, Simcoe, ON , MLS #S13728146 , Image - 1

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Unit-5209, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S13728146

Residential Condo & Other (Other)

$27000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome to Living Water Resort & Spa! Your stunning Collingwood getaway. You could own a fraction of this unit, spend three amazing weeks at Living Wa
23 Photos
Last Updated : 27 Days ago
1725 Earl Haid Avenue, Simcoe, ON , MLS #S13631122 , Image - 1

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1725 Earl Haid Avenue Rural Severn, Severn, Simcoe, ON MLS® S13631122

Residential Freehold (Store W Apartment/Office)

$499900.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Seller says bring all offers. Prime Commercial & Residential Opportunity on the Severn River. Live, work, or invest in cottage country! This unique mi
29 Photos
Last Updated : 27 Days ago
85 THEME PARK Drive, Simcoe, ON , MLS #S13000878 , Image - 1

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Unit-75, 85 THEME PARK Drive Wasaga Beach, Simcoe, ON MLS® S13000878

Residential Freehold (MobileTrailer)

$157500.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
New Add-a-room 12x18 and 22foot hard roof, new flooring, amazing addition to this stunning unit. Enjoy breathtaking forest views and a short walk to
48 Photos
Last Updated : 27 Days ago
174 Barrie Road, Simcoe, ON , MLS #S13099924 , Image - 1

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174 Barrie Road Orillia, Simcoe, ON MLS® S13099924

Residential Freehold (Duplex)

$478900.0
price drop iconPrice drop by 7.7%
  • 1 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
The Price is Right!!! This legal 2-unit home (duplex) sits on an exceptionally deep lot (46.42ft x 196.66ft x 40.29ft x 173.19ft) just off Memorial Dr
49 Photos
Last Updated : 27 Days ago
11401 Highway 12 N/A, Simcoe, ON , MLS #S13562012 , Image - 1

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11401 Highway 12 N/A Coldwater, Severn, Simcoe, ON MLS® S13562012

Residential Freehold (Detached)

$380000.0
price drop iconPrice drop by 5.0%
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to country living on 1.3 acres! Ideally situated between Orillia and Coldwater, this 2-bedroom, 2-bath home presents an excellent opportunity
29 Photos
Last Updated : 27 Days ago
21 Laguna Parkway, Simcoe, ON , MLS #S13726862 , Image - 1

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Unit-16, 21 Laguna Parkway Rural Ramara, Ramara, Simcoe, ON MLS® S13726862

Residential Condo & Other (Condo Townhouse)

$388000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Enjoy tranquil views and direct boating access to Lake Simcoe and the Trent-Severn Waterway, with a private
1 Photos
Last Updated : 27 Days ago
247 Dignard Avenue, Simcoe, ON
247 Dignard Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13431954

Residential Freehold (Vacant Land)

$54900.0
price drop iconPrice drop by 15.4%
Don't wait to invest! Invest and wait! This property currently has a TT designation. There is opportunity to get in the next lottery through Tay Towns
28 Photos
Last Updated : 27 Days ago
55H Chaucer Crescent, Simcoe, ON , MLS #S13674738 , Image - 1

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55H Chaucer Crescent Sunnidale, Barrie, Simcoe, ON MLS® S13674738

Residential Freehold (Detached)

$499999.0
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
This Detached Split-Level Residence Is Perfect For First Time Buyers, Downsizers, Or Savvy Investors. A Functional Multi-Level Layout, Providing The P
36 Photos
Last Updated : 28 Days ago
38 Linden Lane, Simcoe, ON , MLS #N13721782 , Image - 1

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38 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13721782

Residential Freehold (Detached)

$449900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Are you looking to downsize and start living easy and stress-free? This move-in-ready 2-bedroom, 2-bathroom home in Sandy Cove Acres offers comfortabl
25 Photos
Last Updated : 29 Days ago
38 Temagami Trail, Simcoe, ON , MLS #S13140620 , Image - 1

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38 Temagami Trail Wasaga Beach, Simcoe, ON MLS® S13140620

Residential Freehold (MobileTrailer)

$174999.0
price drop iconPrice drop by 5.4%
  • 3 Beds
  • 2 Baths
  • 700-1100 sq-ft
Escape to resort-style living at the highly sought-after Popular Country Life Resort! This beautifully maintained seasonal mobile trailer offers 7 mon
29 Photos
Last Updated : 29 Days ago
1059 Glen Mhor Crescent, Simcoe, ON , MLS #S13703630 , Image - 1

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1059 Glen Mhor Crescent Midland, Simcoe, ON MLS® S13703630

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 1059 Glen Mhor Crescent, a home that offers something buyers are always searching for but rarely find at this price point: space, privacy,
49 Photos
Last Updated : 29 Days ago
375 Sea Ray Avenue, Simcoe, ON , MLS #N13437810 , Image - 1

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Unit-202, 375 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13437810

Residential Condo & Other (Condo Apartment)

$398888.0
  • 1 Beds
  • 1 Baths
  • 600-699 sq-ft
Short Term Rental Allowed! Experience resort-style living at its finest in this beautifully updated 1-bedroom condo at Friday Harbour Resort. Featurin
29 Photos
Last Updated : 29 Days ago
18 Briarwood Place, Simcoe, ON , MLS #N13532598 , Image - 1

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18 Briarwood Place Cookstown, Innisfil, Simcoe, ON MLS® N13532598

Residential Freehold (MobileTrailer)

$399000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Royal Oak Estates. This Senior (Age 55+) Land Lease Community is in the heart ofCookstown.Just a short walk from the Shops and Restaurants,
33 Photos
Last Updated : 29 Days ago
13 JIDAMO MIIKAANS N/A, Simcoe, ON , MLS #S13105284 , Image - 1

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13 JIDAMO MIIKAANS N/A Beausoleil First Nation, Christian Island 30, Simcoe, ON MLS® S13105284

Residential Condo & Other (Other)

$339900.0
price drop iconPrice drop by 8.1%
  • 4 Beds
  • 3 Baths
  • 1400-1599 sq-ft
If you every wanted a great island cottage just steps from a Caribbean Like sandy beach in the sunshine overlooking the clear blue waters of Georgian
32 Photos
Last Updated : 30 Days ago
4266 Canal Road, Simcoe, ON , MLS #S13700914 , Image - 1

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4266 Canal Road Washago, Severn, Simcoe, ON MLS® S13700914

Residential Freehold (Detached)

$245000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Escape to the water in this charming 2-bedroom, 1-bathroom cottage nestled on lease land in beautiful Washago. Enjoy direct waterfront on the Trent-Se
6 Photos
Last Updated : 30 Days ago
7346 County Rd 9 Road, Simcoe, ON , MLS #S13248214 , Image - 1

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7346 County Rd 9 Road Creemore, Clearview, Simcoe, ON MLS® S13248214

Residential Freehold (Vacant Land)

$275000.0
price drop iconPrice drop by 8.0%
Enjoy excellent sun exposure on this beautiful, partially cleared lot, offering just over 3/4 of an acre of land and privacy, just minutes from the he
27 Photos
Last Updated : 30 Days ago
63 Ferris Lane, Simcoe, ON , MLS #S13215654 , Image - 1

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63 Ferris Lane
Unit-I7, 63 Ferris Lane Cundles East, Barrie, Simcoe, ON MLS® S13215654

Residential Condo & Other (Condo Townhouse)

$389000.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
*ATTENTION INVESTORS and FIRST TIME BUYERS! Bright and welcoming 3-bedroom end-unit condo townhome nestled in a family-friendly neighbourhood. The per
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