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Houses for Sale in Simcoe Under $500K - P20

Showing results 571 - 600 of 1094
Last Updated: August 14, 2026
  • New Listings
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7 Photos
Last Updated : 27 Days ago
Lot 354 Desroches Trail NW, Simcoe, ON , MLS #S13578294 , Image - 1
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Lot 354 Desroches Trail NW Rural Tiny, Tiny, Simcoe, ON MLS® S13578294

Residential Freehold (Vacant Land)

$219000.0
TINY!!! BEST DESTINATION TO LIVE YOUR DREAMS. BUILD YOUR DREAM HOME AT THE BEACH! This one of a kind 100x150 corner lot is within 1 minutes to Lafonta
17 Photos
Last Updated : 27 Days ago
34 Dawson Drive, Simcoe, ON , MLS #S13149144 , Image - 1

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Unit-825, 34 Dawson Drive Collingwood, Simcoe, ON MLS® S13149144

Residential Condo & Other (Condo Townhouse)

$425000.0
price drop iconPrice drop by 5.6%
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome to 34 Dawson Drive, Unit 825, a unique and versatile upper-level condo located in Collingwood's sought-after Living Stone Resort community. Th
23 Photos
Last Updated : 27 Days ago
356 West Street N, Simcoe, ON , MLS #S13577842 , Image - 1

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356 West Street N Orillia, Simcoe, ON MLS® S13577842

Residential Freehold (Detached)

$474900.0
  • 4 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 356 West St N in Orillia's desirable North Ward. This affordable four-bedroom home offers plenty of space for families, first-time buyers,
1 Photos
Last Updated : 27 Days ago
2558 25th Side Road, Simcoe, ON
2558 25th Side Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13008324

Residential Freehold (Vacant Land)

$325000.0
price drop iconPrice drop by 7.1%
An exceptional opportunity to acquire a large, cleared residential building lot measuring approximately 115 ft x 200 ft, ideally situated in the charm
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
14 Photos
Last Updated : 27 Days ago
117 Fox Street, Simcoe, ON , MLS #S13577448 , Image - 1

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117 Fox Street Penetanguishene, Simcoe, ON MLS® S13577448

Residential Freehold (Detached)

$323000.0
  • 4 Beds
  • 1 Baths
  • 1500-2000 sq-ft
Prime Investment in Penetanguishene Attention investors and flippers! This solid 4-bedroom home sits on an impressive 0.54-acre lot (89 ft x 264 ft),
5 Photos
Last Updated : 27 Days ago
128 58th Street S, Simcoe, ON , MLS #S12871356 , Image - 1
128 58th Street S Wasaga Beach, Simcoe, ON MLS® S12871356

Residential Freehold (Vacant Land)

$199900.0
price drop iconPrice drop by 23.1%
Build your new home at the best location in Wasaga Beach. Just minutes to good schools, shopping at the Real Canadian Superstore and the soon-to-be-bu
6 Photos
Last Updated : 27 Days ago
149 Minnesota Street, Simcoe, ON , MLS #S12684652 , Image - 1

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149 Minnesota Street Collingwood, Simcoe, ON MLS® S12684652

Residential Freehold (Vacant Land)

$399900.0
price drop iconPrice drop by 11.1%
Incredible opportunity to build your dream home on this newly created lot on desirable Minnesota St. This is an exceptional opportunity as the lot has
10 Photos
Last Updated : 27 Days ago
94 Simcoe Road, Simcoe, ON , MLS #S13576922 , Image - 1

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94 Simcoe Road Brechin, Ramara, Simcoe, ON MLS® S13576922

Residential Freehold (Vacant Land)

$189900.0
Here's a rare chance to build in one of Simcoe County's most established waterfront communities. This vacant lot - approximately 50' x 150' (roughly 7
22 Photos
Last Updated : 27 Days ago
28 Harriet Street, Simcoe, ON , MLS #S13576262 , Image - 1

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28 Harriet Street Penetanguishene, Simcoe, ON MLS® S13576262

Residential Freehold (Detached)

$399900.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to this charming 3-bedroom bungalow nestled on a generous 49' x 165' lot in the heart of Penetanguishene. This home is an excellent opportunit
30 Photos
Last Updated : 27 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
11 Photos
Last Updated : 27 Days ago
Lot 102 Emilio Street, Simcoe, ON , MLS #S13575644 , Image - 1

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Lot 102 Emilio Street Rural Tiny, Tiny, Simcoe, ON MLS® S13575644

Residential Freehold (Vacant Land)

$399000.0
Located in the desirable neighborhood of Bluewater Beach. Less than a ten minute walk to the boardwalk leading to a prime sand beach, stunning sunsets
9 Photos
Last Updated : 28 Days ago
3963 Algonquin Avenue, Simcoe, ON , MLS #N13568116 , Image - 1

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3963 Algonquin Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13568116

Residential Freehold (Vacant Land)

$339000.0
Rare Opportunity To Own A Fully Severed Building Lot In The Desirable Big Bay Community! This **50 Ft. X 150 Ft.** Building Lot Is Just Steps To The S
27 Photos
Last Updated : 28 Days ago
1 Paradise Boulevard, Simcoe, ON , MLS #S13109300 , Image - 1

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Unit-26, 1 Paradise Boulevard Rural Ramara, Ramara, Simcoe, ON MLS® S13109300

Residential Condo & Other (Condo Townhouse)

$425000.0
price drop iconPrice drop by 6.4%
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Three Bedroom End Unit Condo in Beautiful Lagoon City Just Steps Away From Private Park & Sandy Beach on Lake Simcoe. Condo Offers Lots of Windows, Wa
5 Photos
Last Updated : 28 Days ago
9 HARBOUR Street E, Simcoe, ON , MLS #S12720304 , Image - 1
Unit-6201-03, 9 HARBOUR Street E Collingwood, Simcoe, ON MLS® S12720304

Residential Condo & Other (Condo Apartment)

$40000.0
price drop iconPrice drop by 20.0%
  • 2 +0 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Invest in an ownership share of Phase 2 of LIVING WATER RESORT AND SPA on the shores of Georgian Bay in the beautiful town of Collingwood. NOTE: this
47 Photos
Last Updated : 28 Days ago
440 David Avenue, Simcoe, ON , MLS #S13572922 , Image - 1

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440 David Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13572922

Residential Freehold (Vacant Land)

$119900.0
HERE'S WHY 440 DAVID AVENUE COULD BE YOUR NEXT MOVE: READY FOR YOUR VISION - Whether you're dreaming of your first home, your forever home, or a peac
12 Photos
Last Updated : 28 Days ago
111 Worsley Street SW, Simcoe, ON , MLS #S13491694 , Image - 1

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Unit-401, 111 Worsley Street SW City Centre, Barrie, Simcoe, ON MLS® S13491694

Residential Condo & Other (Condo Apartment)

$399000.0
price drop iconPrice drop by 1.5%
  • 1 Beds
  • 1 Baths
  • 600-699 sq-ft
Welcome to Downtown Living at 111 Worsley Street, Barrie! Experience the perfect blend of urban convenience and modern comfort in the heart of Barrie'
38 Photos
Last Updated : 28 Days ago
183 Paradise Avenue, Simcoe, ON , MLS #S13127128 , Image - 1

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183 Paradise Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13127128

Residential Freehold (Detached)

$379000.0
price drop iconPrice drop by 5.2%
  • 3 Beds
  • 1 Baths
  • < 700 sq-ft
Welcome to 183 Paradise Avenue, this 3-bedroom, 1-bath home located in the heart of beautiful Port McNicoll. Just minutes from the waterfront, this pr
23 Photos
Last Updated : 28 Days ago
9 Hawthorne Drive, Simcoe, ON , MLS #N13572328 , Image - 1

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9 Hawthorne Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13572328

Residential Freehold (Modular Home)

$279000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Sandycove Acres, one of Innisfil's most sought-after adult lifestyle communities, where resort-style amenities and a welcoming neighbourhoo
38 Photos
Last Updated : 28 Days ago
6449 12 13 Side Road, Simcoe, ON , MLS #S12562460 , Image - 1

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6449 12 13 Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S12562460

Residential Freehold (Vacant Land)

$425000.0
Just imagine... it's a year of firsts in your newly built home at 6449 12/13 Sideroad. A home designed exactly the way you've always envisioned. Outs
30 Photos
Last Updated : 28 Days ago
224 Tiny Beaches Road S Road, Simcoe, ON , MLS #S13568156 , Image - 1

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224 Tiny Beaches Road S Road Rural Tiny, Tiny, Simcoe, ON MLS® S13568156

Residential Freehold (Detached)

$424900.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Imagine waking up just steps from the soft sands of Georgian Bay, coffee in hand, with the sound of the waves calling you to the beach. Welcome to you
24 Photos
Last Updated : 28 Days ago
131 Clapperton Street, Simcoe, ON , MLS #S13521982 , Image - 1

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Unit-102, 131 Clapperton Street Wellington, Barrie, Simcoe, ON MLS® S13521982

Residential Condo & Other (Condo Apartment)

$349900.0
  • 2 Beds
  • 1 Baths
  • 1000-1199 sq-ft
Convenient ground level layout in a lovely 3 storey condo. Walking distance to local restaurants, cafes, boutique shopping and Barrie's beautiful wate
36 Photos
Last Updated : 28 Days ago
65 MEADOW Lane, Simcoe, ON , MLS #S13571032 , Image - 1

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65 MEADOW Lane Wasaga Beach, Simcoe, ON MLS® S13571032

Residential Freehold (Att/Row/Townhouse)

$416000.0
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 65 Meadow Lane! Located in the desirable 55+ community of Wasaga Meadows, this home offers a relaxed lifestyle just minutes from the beach,
20 Photos
Last Updated : 28 Days ago
4976 25th Side Road, Simcoe, ON , MLS #N13482028 , Image - 1

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Unit-42, 4976 25th Side Road Rural Essa, Essa, Simcoe, ON MLS® N13482028

Residential Freehold (Modular Home)

$299900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to this well-maintained 2-bedroom home nestled in the peaceful community of Hoe Doe Valley, conveniently located between Barrie, Angus, and Th
6 Photos
Last Updated : 28 Days ago
1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S13234932 , Image - 1

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Unit-309, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13234932

Residential Condo & Other (Condo Apartment)

$364999.0
price drop iconPrice drop by 2.7%
  • 2 Beds
  • 1 Baths
  • 1200-1399 sq-ft
A Place To Get Away Or Stay. Welcome To The Heart Of Horseshoe Valley, Where Four-Season Recreation, Natural Beauty, And Resort-Style Amenities Come
35 Photos
Last Updated : 28 Days ago
308 Hilda Street, Simcoe, ON , MLS #S13418298 , Image - 1

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308 Hilda Street Orillia, Simcoe, ON MLS® S13418298

Residential Freehold (Semi-Detached )

$399000.0
price drop iconPrice drop by 5.5%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Affordable opportunity in Orillia! This 2-storey semi-detached home offers over 1,000 sq ft above grade with 3 bedrooms and 1 full bath, making it a g
50 Photos
Last Updated : 29 Days ago
3 Garden Grove Crescent, Simcoe, ON , MLS #S13242300 , Image - 1

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3 Garden Grove Crescent Wasaga Beach, Simcoe, ON MLS® S13242300

Residential Freehold (Att/Row/Townhouse)

$499900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Country Meadows a peaceful adult lifestyle community in Wasaga Beach. Backing onto the pond with manicured lawns you will find this beautif
25 Photos
Last Updated : 29 Days ago
241 Sea Ray Avenue, Simcoe, ON , MLS #N13568918 , Image - 1

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Unit-A109, 241 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13568918

Residential Condo & Other (Condo Apartment)

$449000.0
  • 1 +1 Beds
  • 1 Baths
  • 600-699 sq-ft
Highly Sought-After Ground Floor Unit with Private Yard & Patio! Enjoy resort-style living at Friday Harbours spectacular waterside community, offerin
17 Photos
Last Updated : 29 Days ago
150 Dunlop Street E, Simcoe, ON , MLS #S13567964 , Image - 1

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Unit-904, 150 Dunlop Street E City Centre, Barrie, Simcoe, ON MLS® S13567964

Residential Condo & Other (Condo Apartment)

$329900.0
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
9TH-FLOOR BAY-VIEW CONDO WITH NEARLY 800 SQ FT, PARKING, LOCKER, IN-SUITE LAUNDRY & DOWNTOWN BARRIE AT YOUR DOOR! Bayshore Landing puts you right wher
29 Photos
Last Updated : 29 Days ago
21 Laguna Parkway, Simcoe, ON , MLS #S13566698 , Image - 1

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Unit-16, 21 Laguna Parkway Rural Ramara, Ramara, Simcoe, ON MLS® S13566698

Residential Condo & Other (Condo Townhouse)

$398000.0
  • 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
36 Photos
Last Updated : 29 Days ago
39 Appletree Lane, Simcoe, ON , MLS #S13567692 , Image - 1

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39 Appletree Lane Innis-Shore, Barrie, Simcoe, ON MLS® S13567692

Residential Condo & Other (Condo Townhouse)

$489900.0
  • 3 Beds
  • 3 Baths
  • 1200-1399 sq-ft
Top 5 Reasons You Will Love This Condo: 1) Ideally located steps away from the Barrie South GO station providing easy access to the GTA, perfect for e
Shortlisted Properties
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