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Houses for Sale in Simcoe Under $500K - P25

Showing results 721 - 750 of 1115
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)
37 Photos
Last Updated : 41 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)

$389000.0
price drop iconPrice drop by 7.2%
  • 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
30 Photos
Last Updated : 41 Days ago
10 Maple Lane, Simcoe, ON , MLS #S13247166 , Image - 1

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10 Maple Lane Midland, Simcoe, ON MLS® S13247166

Residential Freehold (MobileTrailer)

$244000.0
price drop iconPrice drop by 6.1%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Clean, cozy, and move in ready. This bright and tidy 2 bedroom mobile home offers comfortable, affordable living in the heart of Smith's Camp. Enjoy
22 Photos
Last Updated : 41 Days ago
37 Ellen Street, Simcoe, ON , MLS #S13682968 , Image - 1

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Unit-1303, 37 Ellen Street City Centre, Barrie, Simcoe, ON MLS® S13682968

Residential Condo & Other (Condo Apartment)

$449000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
EFFORTLESS CONDO LIVING AT THE NAUTICA WITH PREMIUM AMENITIES & FRONT-ROW VIEWS OF KEMPENFELT BAY! Imagine starting and ending each day with uninterru
50 Photos
Last Updated : 43 Days ago
172 Eighth Street, Simcoe, ON , MLS #S13500320 , Image - 1

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Unit-102, 172 Eighth Street Collingwood, Simcoe, ON MLS® S13500320

Residential Condo & Other (Condo Apartment)

$399000.0
  • 2 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Bright and light 2 bedroom condo on the main floor in The Galleries. This west facing unit boasts ample space with over 1100 sqft; newly installed vin
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
34 Photos
Last Updated : 43 Days ago
435 Walnut Street, Simcoe, ON , MLS #S13631308 , Image - 1

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Unit-206, 435 Walnut Street Collingwood, Simcoe, ON MLS® S13631308

Residential Condo & Other (Condo Apartment)

$359900.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to Walnut Woods-this spacious and beautifully maintained 1-bedroom, 1-bathroom condo is perfectly situated in the heart of Collingwood. With a
33 Photos
Last Updated : 44 Days ago
241 Sea Ray Avenue, Simcoe, ON , MLS #N13234786 , Image - 1

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Unit-A213, 241 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13234786

Residential Condo & Other (Condo Apartment)

$489900.0
price drop iconPrice drop by 4.9%
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
If you're craving that endless summer feeling, this is the place. Welcome to Friday Harbour, Innisfil's all-season playground. This sun-drenched corne
27 Photos
Last Updated : 44 Days ago
78 KING RD N/A, Simcoe, ON , MLS #S13440322 , Image - 1

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78 KING RD N/A Waubaushene, Tay, Simcoe, ON MLS® S13440322

Residential Freehold (Detached)

$299000.0
price drop iconPrice drop by 8.0%
  • 1 +0 Beds
  • 1 Baths
  • < 700 sq-ft
Tucked away on a peaceful dead-end street, 78 King Road offers the perfect blend of modern convenience and classic cottage country charm. This year-ro
7 Photos
Last Updated : 44 Days ago
607 TAYLOR Drive, Simcoe, ON , MLS #S13677582 , Image - 1

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607 TAYLOR Drive Midland, Simcoe, ON MLS® S13677582

Residential Freehold (Vacant Land)

$179900.0
  • < 700 sq-ft
Build Your Dream Home Here. Rare opportunity to own a spacious building lot (60ft Wide x 229ft Deep) backing onto Tiffin Pond in a very desirable Midl
5 Photos
Last Updated : 44 Days ago
6125 Second Concession Road, Simcoe, ON , MLS #S13671832 , Image - 1
6125 Second Concession Road Rural Clearview, Clearview, Simcoe, ON MLS® S13671832

Residential Freehold (Vacant Land)

$479000.0
If you're looking to locate ruraly be sure to check out this maturely treed 25 acres located 20 minutes from Barrie, 10 minutes from shopping, golfing
19 Photos
Last Updated : 44 Days ago
11 INDIANA Avenue, Simcoe, ON , MLS #S13676752 , Image - 1

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11 INDIANA Avenue Wasaga Beach, Simcoe, ON MLS® S13676752

Residential Freehold (Detached)

$359900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Easy living starts here in popular Park Place! This charming 2-bedroom, 888 sq.ft. Conestoga model offers vaulted ceilings, a bright eat-in kitchen &
35 Photos
Last Updated : 44 Days ago
169 MARGARET Street, Simcoe, ON , MLS #N13638942 , Image - 1

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169 MARGARET Street Angus, Essa, Simcoe, ON MLS® N13638942

Residential Freehold (Detached)

$499900.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to this charming & clean 1.5-storey home, offering 968 square feet of bright, inviting living space. Featuring 2 bedrooms plus a dedicated off
28 Photos
Last Updated : 44 Days ago
375 Horrell Avenue, Simcoe, ON , MLS #S13674652 , Image - 1

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375 Horrell Avenue Midland, Simcoe, ON MLS® S13674652

Residential Freehold (Detached)

$449777.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 375 Horrell Avenue in Midland, a great opportunity for first-time buyers, investors, or those looking for an affordable home in a convenien
14 Photos
Last Updated : 44 Days ago
99 King Street, Simcoe, ON , MLS #N13666450 , Image - 1

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99 King Street Angus, Essa, Simcoe, ON MLS® N13666450

Residential Freehold (Detached)

$444900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable Opportunity in Angus! This charming bungalow built in 1895 is a fantastic option for a first-time buyer, handyman, or contractor looking fo
16 Photos
Last Updated : 44 Days ago
5609 Line 4 N/A N, Simcoe, ON , MLS #S13672416 , Image - 1

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5609 Line 4 N/A N Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13672416

Residential Freehold (Vacant Land)

$399999.0
Top 5 Reasons You Will Love This Property: 1) Picturesque 3.16-acre building lot in the desirable Moonstone Mount St. Louis area, offering a peaceful
31 Photos
Last Updated : 45 Days ago
11 Cabin Crescent, Simcoe, ON , MLS #S13668114 , Image - 1

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11 Cabin Crescent Wasaga Beach, Simcoe, ON MLS® S13668114

Residential Freehold (Detached)

$429900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
**NEW PRICE - YOUR YEAR-ROUND COTTAGE RETREAT AWAITS!** Discover this inviting 3-bedroom cottage in Wasaga CountryLife, beautifully situated overlooki
9 Photos
Last Updated : 45 Days ago
1963 Lot 52 Tiny Beaches Road N, Simcoe, ON , MLS #S13673102 , Image - 1

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1963 Lot 52 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S13673102

Residential Freehold (Vacant Land)

$299900.0
Partially cleared 3/4 acre lot in desirable Georgian Highlands on the Great Lakes Waterfront Trail with exclusive community use of 3 private beaches o
3 Photos
Last Updated : 45 Days ago
2143 North Orr Lake Road, Simcoe, ON , MLS #S13668228 , Image - 1
2143 North Orr Lake Road Rural Springwater, Springwater, Simcoe, ON MLS® S13668228

Residential Freehold (Vacant Land)

$300000.0
  • < 700 sq-ft
Create the family lake retreat you've always imagined on beautiful Orr Lake. Offering 97 feet of owned waterfront and a generous lot, this exceptional
4 Photos
Last Updated : 45 Days ago
2137 North Orr Lake Road N, Simcoe, ON , MLS #S13668206 , Image - 1
2137 North Orr Lake Road N Elmvale, Springwater, Simcoe, ON MLS® S13668206

Residential Freehold (Rural Residential)

$385000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to life on beautiful Orr Lake, where peaceful mornings begin with spectacular sunrises over the water and evenings are best spent watching the
34 Photos
Last Updated : 45 Days ago
157 WELLINGTON Street E, Simcoe, ON , MLS #N13673038 , Image - 1

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Unit-404, 157 WELLINGTON Street E Alliston, New Tecumseth, Simcoe, ON MLS® N13673038

Residential Condo & Other (Condo Apartment)

$499999.0
  • 1 +0 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to easy, low-maintenance living in this bright and beautifully maintained top-floor condo! This spacious 1-bedroom, 1-bathroom unit features a
20 Photos
Last Updated : 45 Days ago
2 Shamrock Crescent, Simcoe, ON , MLS #N13471164 , Image - 1

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2 Shamrock Crescent Rural Essa, Essa, Simcoe, ON MLS® N13471164

Residential Freehold (MobileTrailer)

$333000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Visit REALTOR website for additional information.1st Time Home Buyers - Great Opportunity to own your our place! Recently Renovated Double Wide Modula
38 Photos
Last Updated : 45 Days ago
18 Prince Charles Avenue, Simcoe, ON , MLS #S13067922 , Image - 1

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18 Prince Charles Avenue Rural Springwater, Springwater, Simcoe, ON MLS® S13067922

Residential Freehold (MobileTrailer)

$185000.0
price drop iconPrice drop by 2.6%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Wasaga Pines, with extended nine (9) months occupancy . This recreational lifestyle includes shared use of 2 pools, playground, volley ball
15 Photos
Last Updated : 45 Days ago
3958 Parkside Drive, Simcoe, ON , MLS #S13672684 , Image - 1

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3958 Parkside Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13672684

Residential Freehold (Vacant Land)

$295000.0
70 X 248 FT BUILDING LOT NEAR LAKE SIMCOE WITH WELL, SEPTIC & SHORELINE RESIDENTIAL ZONING! A future home or cottage near the water starts with the ri
12 Photos
Last Updated : 45 Days ago
167 Edgehill Drive, Simcoe, ON , MLS #S13641080 , Image - 1

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Unit-E9, 167 Edgehill Drive Letitia Heights, Barrie, Simcoe, ON MLS® S13641080

Residential Condo & Other (Condo Apartment)

$329900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
TOP FLOOR 2 BEDROOM CONDO WITH A FUNCTIONAL LAYOUT, PRIVATE BALCONY, PARKING, & QUICK ACCESS TO EVERYTHING! Maybe you're just starting out, maybe you'
11 Photos
Last Updated : 45 Days ago
302 Essa Road, Simcoe, ON , MLS #S13620792 , Image - 1

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Unit-203, 302 Essa Road Ardagh, Barrie, Simcoe, ON MLS® S13620792

Residential Condo & Other (Condo Apartment)

$464900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to The Gallery in Barrie, where comfort, convenience, and lifestyle come together. This beautifully appointed 2-bedroom, 2-bathroom suite offe
2 Photos
Last Updated : 45 Days ago
14 Rogers Road, Simcoe, ON , MLS #N13671870 , Image - 1
14 Rogers Road Alliston, New Tecumseth, Simcoe, ON MLS® N13671870

Residential Freehold (Vacant Land)

$250000.0
Vacant Residential Lot for Sale - 50' x 91'Build your dream home on this beautiful vacant residential lot located in a lovely, welcoming town. Situate
26 Photos
Last Updated : 45 Days ago
30 Joseph Trail, Simcoe, ON , MLS #S13670478 , Image - 1

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30 Joseph Trail Collingwood, Simcoe, ON MLS® S13670478

Residential Condo & Other (Condo Townhouse)

$469000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to 30 Joseph Trail in the sought-after Tanglewood community of Collingwood! This exceptionally well-cared-for 2-bedroom, 2-bathroom townhouse
5 Photos
Last Updated : 45 Days ago
1459 River Road W, Simcoe, ON , MLS #S13096602 , Image - 1
1459 River Road W Wasaga Beach, Simcoe, ON MLS® S13096602

Residential Freehold (Vacant Land)

$200000.0
Opportunity to build your custom home on this large 93' x 282' lot in the heart of Wasaga Beach. This unique property offers a sprawling canvas for a
1 Photos
Last Updated : 45 Days ago
61 Front Street S, Simcoe, ON
61 Front Street S Orillia, Simcoe, ON MLS® S12921296

Residential Freehold (Vacant Land)

$129000.0
price drop iconPrice drop by 63.1%
Welcome to 61 Front Street in the heart of Orillia-where charm, convenience, and opportunity come together. Ideally located just steps from the vibran
38 Photos
Last Updated : 46 Days ago
3 Lavender Hill Road, Simcoe, ON , MLS #S13667048 , Image - 1

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3 Lavender Hill Road Rural Clearview, Clearview, Simcoe, ON MLS® S13667048

Residential Freehold (Vacant Land)

$369000.0
A truly unique opportunity in the heart of Dunedin! Set along the banks of Mill Creek, this picturesque property offers over an acre of serene country
32 Photos
Last Updated : 46 Days ago
100 Dean Avenue, Simcoe, ON , MLS #S13665758 , Image - 1

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Unit-105, 100 Dean Avenue Painswick South, Barrie, Simcoe, ON MLS® S13665758

Residential Condo & Other (Condo Apartment)

$419900.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to 100 Dean Ave unit 105 comfortable and bright 1 bedroom, 1 bathroom condo. 9' ceilings, large windows, loads of natural light. Walk-out to a
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