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Houses for Sale in Simcoe Under $500K - P18

Showing results 511 - 540 of 1094
Last Updated: August 14, 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 : 21 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)

$299777.0
  • 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 : 21 Days ago
1 Smiths Lane, Simcoe, ON , MLS #S13531568 , Image - 1

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1 Smiths Lane Midland, Simcoe, ON MLS® S13531568

Residential Freehold (MobileTrailer)

$349000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 1 Smiths Lane Road. Looking for an affordable home with more space for less? This spacious 2-bedroom, 1.5 bath home is located in Smith's C
17 Photos
Last Updated : 21 Days ago
808 Jane Boulevard, Simcoe, ON , MLS #S13596314 , Image - 1

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808 Jane Boulevard Midland, Simcoe, ON MLS® S13596314

Residential Condo & Other (Condo Townhouse)

$429900.0
  • 2 +0 Beds
  • 2 Baths
  • 1200-1399 sq-ft
This affordable property is priced to sell and ready to make your own. Don't judge a book by its cover! You will be pleasantly surprized by the size o
12 Photos
Last Updated : 21 Days ago
5263 Elliott Side Road, Simcoe, ON , MLS #S12899952 , Image - 1

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Unit-37, 5263 Elliott Side Road Rural Tay, Tay, Simcoe, ON MLS® S12899952

Residential Freehold (MobileTrailer)

$299900.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Bramhall Park Estates. Are you looking to enter the market or downsize close to nature? This quiet, comfortable living in a country communi
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
46 Photos
Last Updated : 22 Days ago
441 Barrie Road, Simcoe, ON , MLS #S13509204 , Image - 1

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Unit-35, 441 Barrie Road Orillia, Simcoe, ON MLS® S13509204

Residential Condo & Other (Condo Townhouse)

$399900.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Affordable Homeownership in Orillia's Woodlands Community! This neat & tidy 3 Bedroom townhouse offers an excellent opportunity for first-time buyers,
37 Photos
Last Updated : 22 Days ago
23 Maria Street, Simcoe, ON , MLS #S13251390 , Image - 1

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23 Maria Street Penetanguishene, Simcoe, ON MLS® S13251390

Residential Freehold (Detached)

$399000.0
price drop iconPrice drop by 4.8%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Endless Potential Meets Small-Town Charm On A Large Lot At 23 Maria Street In The Heart Of Penetanguishene. This 3-Bedroom, 1-Bathroom Home Presents A
9 Photos
Last Updated : 22 Days ago
40 Georgian Glen Drive, Simcoe, ON , MLS #S12961494 , Image - 1

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40 Georgian Glen Drive Wasaga Beach, Simcoe, ON MLS® S12961494

Residential Freehold (Modular Home)

$249900.0
price drop iconPrice drop by 10.7%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
This beautifully maintained two-bedroom, one-bath modular home on leased land offers the perfect blend of comfort and convenience. Ideally located jus
4 Photos
Last Updated : 22 Days ago
8926 Mckinnon Road, Simcoe, ON , MLS #N13486348 , Image - 1
8926 Mckinnon Road Rural Essa, Essa, Simcoe, ON MLS® N13486348

Residential Freehold (Detached)

Price On Request
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Once-in-a-generation opportunity on 24 acres in fast-growing Angus. A solid 4-bedroom detached home anchors the property today, while approximately 10
34 Photos
Last Updated : 22 Days ago
4 Beck Boulevard, Simcoe, ON , MLS #S13595046 , Image - 1

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Unit-302, 4 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13595046

Residential Condo & Other (Condo Apartment)

$429900.0
  • 1 +1 Beds
  • 2 Baths
  • 900-999 sq-ft
Boat. Relax. Explore. Where waterfront living meets carefree condominium ownership. This unit includes a boat slip with water & hydro, secure undergro
12 Photos
Last Updated : 22 Days ago
6308 9 NORTH Line, Simcoe, ON , MLS #S13415690 , Image - 1

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6308 9 NORTH Line Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13415690

Residential Freehold (Vacant Land)

$349900.0
price drop iconPrice drop by 12.5%
Discover the potential of this beautiful treed vacant lot just over one acre in the charming community of rural Waubaushene. Surrounded by nature and
47 Photos
Last Updated : 22 Days ago
2 Paradise Boulevard, Simcoe, ON , MLS #S13594524 , Image - 1

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Unit-Unit 20, 2 Paradise Boulevard Rural Ramara, Ramara, Simcoe, ON MLS® S13594524

Residential Condo & Other (Common Element Condo)

$414900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Have you ever dreamed of living just steps from a beautiful sandy beach? There's a reason it's called Paradise Boulevard! Welcome to this move-in read
15 Photos
Last Updated : 22 Days ago
9 Wolfe Street, Simcoe, ON , MLS #S13571870 , Image - 1

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9 Wolfe Street Penetanguishene, Simcoe, ON MLS® S13571870

Residential Freehold (Detached)

$399900.0
  • 4 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 9 Wolfe Street in the heart of Penetanguishene! This spacious bungalow offers exceptional potential for first-time buyers, families, or inv
47 Photos
Last Updated : 22 Days ago
5 Anchorage Crescent, Simcoe, ON , MLS #S13474236 , Image - 1

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Unit-104, 5 Anchorage Crescent Collingwood, Simcoe, ON MLS® S13474236

Residential Condo & Other (Condo Townhouse)

$499000.0
price drop iconPrice drop by 3.9%
  • 1 +1 Beds
  • 2 Baths
  • 800-899 sq-ft
WYLDWOOD COVE, GROUND level one bedroom plus den with 2 bathrooms. This sought after waterfront community is located on the shores of Georgian Bay an
7 Photos
Last Updated : 22 Days ago
1382 Wilson Point Road, Simcoe, ON , MLS #S12970742 , Image - 1

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1382 Wilson Point Road Orillia, Simcoe, ON MLS® S12970742

Residential Freehold (Vacant Land)

$289000.0
price drop iconPrice drop by 3.3%
Private vacant parcel located 400 m from Lake Couchiching, with just over 2 acres and nearly 500 ft of road frontage. A rare opportunity to build a cu
14 Photos
Last Updated : 22 Days ago
126 Bell Farm Road, Simcoe, ON , MLS #S13593470 , Image - 1

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Unit-414, 126 Bell Farm Road Alliance, Barrie, Simcoe, ON MLS® S13593470

Residential Condo & Other (Condo Apartment)

$309900.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Nestled in the vibrant north end of Barrie, this location places every convenience at your doorstep. You are only minutes away from Georgian College,
14 Photos
Last Updated : 22 Days ago
857 Birchwood Drive, Simcoe, ON , MLS #S13537548 , Image - 1

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857 Birchwood Drive Midland, Simcoe, ON MLS® S13537548

Residential Freehold (Detached)

$449000.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
SUN-FILLED BUNGALOW LIVING JUST MINUTES FROM MIDLAND'S WATERFRONT! Escape to a peaceful, tree-lined neighbourhood where quiet streets, mature trees, a
24 Photos
Last Updated : 22 Days ago
32 Temagami Trail, Simcoe, ON , MLS #S13592610 , Image - 1

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32 Temagami Trail Wasaga Beach, Simcoe, ON MLS® S13592610

Residential Freehold (MobileTrailer)

$115000.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Escape to the beauty of Wasaga Beach with this charming 2-bedroom seasonal Northlander Cottager Escape, ideally situated in the highly sought-after Wa
41 Photos
Last Updated : 22 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)

$475000.0
  • 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
21 Photos
Last Updated : 22 Days ago
3 Northland Road, Simcoe, ON , MLS #S13492936 , Image - 1

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3 Northland Road Midland, Simcoe, ON MLS® S13492936

Residential Freehold (MobileTrailer)

$253900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable Living with Great Amenities! Looking for an affordable home with extras you don't usually get at this price? This charming 2-bedroom, 1-bat
17 Photos
Last Updated : 23 Days ago
97 Georgian Glen Drive, Simcoe, ON , MLS #S13587376 , Image - 1

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97 Georgian Glen Drive Wasaga Beach, Simcoe, ON MLS® S13587376

Residential Freehold (Modular Home)

$325000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Move-in ready home at the end of a cul-de-sac in the family friendly community of Georgian Glen Estates! This home features a rarely offered bonus roo
23 Photos
Last Updated : 23 Days ago
8 Myrtle Avenue, Simcoe, ON , MLS #S13578972 , Image - 1

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8 Myrtle Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13578972

Residential Freehold (Detached)

$499900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Fully Renovated From Top To Bottom Over The Last 5 Years! Completely Turn-Key, Cozy Bungalow Situated On Large 50 x 110 Ft Lot With No Neighbours Behi
17 Photos
Last Updated : 23 Days ago
15 English Drive, Simcoe, ON , MLS #N13566572 , Image - 1

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15 English Drive Beeton, New Tecumseth, Simcoe, ON MLS® N13566572

Residential Freehold (Vacant Land)

$149990.0
Vacant Lot Opportunity In The Heart Growing Town Of Beeton. Large Mature Lot, Located On Quiet Street Walking Distance to 2 Elementary Schools, Close
22 Photos
Last Updated : 23 Days ago
5263 Elliott Side Road, Simcoe, ON , MLS #S13577578 , Image - 1

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Unit-48, 5263 Elliott Side Road Rural Tay, Tay, Simcoe, ON MLS® S13577578

Residential Freehold (MobileTrailer)

$159000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable homeownership is becoming increasingly difficult to find-especially at this price point. Located in Bramhall Park Estates, this 2-bedroom,
27 Photos
Last Updated : 23 Days ago
415 Sea Ray Avenue, Simcoe, ON , MLS #N13576666 , Image - 1

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Unit-326, 415 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13576666

Residential Condo & Other (Condo Apartment)

$418800.0
  • 1 Beds
  • 1 Baths
  • 500-599 sq-ft
Professionally Designed w/Lots of Upgrades & Overlooking The Courtyard Pool & All-Year-Round Hot Tub! Premium Turnkey Unit Ready For You! Upgrades Inc
29 Photos
Last Updated : 23 Days ago
1981 Tiny Beaches Road S, Simcoe, ON , MLS #S13236488 , Image - 1

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1981 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13236488

Residential Freehold (Detached)

$369900.0
price drop iconPrice drop by 7.5%
  • 3 Beds
  • 1 Baths
  • < 700 sq-ft
SPOTLESS AND WELL MAINTAINED 3 SEASON COTTAGE IN TINY BEACHES, SHORT DISTANCE TO WOODLAND BEACH AND EASY ACCESS TO CONVENIENCE STORE AND SHORT DISTAN
28 Photos
Last Updated : 23 Days ago
9 EARLDOM Boulevard, Simcoe, ON , MLS #S13498684 , Image - 1

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9 EARLDOM Boulevard Port McNicoll, Tay, Simcoe, ON MLS® S13498684

Residential Freehold (Detached)

$399900.0
price drop iconPrice drop by 3.6%
  • 3 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Steps from Grandview Beach! This charming 3-season cottage offers a wonderful opportunity to enjoy relaxed summer living just a short stroll from the
30 Photos
Last Updated : 23 Days ago
32 Lorne Avenue, Simcoe, ON , MLS #S13544582 , Image - 1

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32 Lorne Avenue Collingwood, Simcoe, ON MLS® S13544582

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) Rare opportunity to secure an oversized approximately 66'x132' lot in the heart of Collingwood, where you ca
9 Photos
Last Updated : 23 Days ago
173 EIGHTH Street, Simcoe, ON , MLS #S13158540 , Image - 1

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Unit-101, 173 EIGHTH Street Collingwood, Simcoe, ON MLS® S13158540

Residential Condo & Other (Condo Apartment)

$315000.0
  • 1 +0 Beds
  • 1 Baths
  • 700-799 sq-ft
This bright and inviting one-bedroom, one-bathroom ground floor condo features an open-concept layout and a spacious private patio, perfect for relaxi
39 Photos
Last Updated : 23 Days ago
2 Bernick Drive, Simcoe, ON , MLS #S13587782 , Image - 1

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Unit-23, 2 Bernick Drive Grove East, Barrie, Simcoe, ON MLS® S13587782

Residential Condo & Other (Condo Townhouse)

$469900.0
  • 3 Beds
  • 3 Baths
  • 1400-1599 sq-ft
Welcome to this beautifully renovated and meticulously maintained townhome featuring quality finishes that offer both comfort and peace of mind. The s
1 Photos
Last Updated : 23 Days ago
0000 Tanager Crescent, Simcoe, ON
0000 Tanager Crescent Wasaga Beach, Simcoe, ON MLS® S13040122

Residential Freehold (Vacant Land)

$164900.0
price drop iconPrice drop by 17.5%
Build Your DREAM HOME in a very quiet, peaceful and Established neighbourhood of Wasaga Beach. All the SERVICES are at the lot line, READY to start c
Shortlisted Properties
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