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Houses for Sale in Simcoe Under $500K - P26

Showing results 751 - 780 of 1024
Last Updated: November 12, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
11 Photos
Last Updated : 54 Days ago
LT 19 BUCHANAN Street, Simcoe, ON , MLS #N13107606 , Image - 1
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LT 19 BUCHANAN Street Alcona, Innisfil, Simcoe, ON MLS® N13107606

Residential Freehold (Vacant Land)

$189000.0
  • < 700 sq-ft
Located in a desirable, family-friendly neighbourhood, Lot 19 offers an excellent location just steps from the beaches of Lake Simcoe at 9th Line. The
11 Photos
Last Updated : 54 Days ago
LT 20 BUCHANAN Street, Simcoe, ON , MLS #N13107604 , Image - 1

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LT 20 BUCHANAN Street Alcona, Innisfil, Simcoe, ON MLS® N13107604

Residential Freehold (Vacant Land)

$189000.0
  • < 700 sq-ft
Located in a desirable, family-friendly neighbourhood, Lot 19 offers an excellent location just steps from the beaches of Lake Simcoe at 9th Line. The
21 Photos
Last Updated : 54 Days ago
9 Harbour Street E, Simcoe, ON , MLS #S12562086 , Image - 1

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Unit-4119, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12562086

Residential Condo & Other (Timeshare)

$19000.0
price drop iconPrice drop by 67.2%
  • 1 Beds
  • 1 Baths
  • 900-999 sq-ft
Exclusive Waterfront Ownership - Living Water Resort & Spa, Collingwood. Three Premium Weeks of Luxury, Lifestyle & Flexibility2026 is prepaid already
32 Photos
Last Updated : 55 Days ago
40 Horseshoe Boulevard, Simcoe, ON , MLS #S13801576 , Image - 1

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Unit-107, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13801576

Residential Condo & Other (Condo Apartment)

$431000.0
  • 1 +1 Beds
  • 2 Baths
  • 700-799 sq-ft
**RARE GROUND-FLOOR MOUNTAIN-VIEW SUITE AT HORSESHOE RESORT!** Imagine waking up to beautiful ski hill views, stepping directly onto your private gard
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
8 Photos
Last Updated : 55 Days ago
50 DUNEDIN Street, Simcoe, ON , MLS #S13440270 , Image - 1

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50 DUNEDIN Street Orillia, Simcoe, ON MLS® S13440270

Residential Freehold (Detached)

$399000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
The property includes an approximately 1,100 sq. ft. house currently rented for $950 per month plus utilities and is in poor condition. The house has
6 Photos
Last Updated : 55 Days ago
3678 McCarthy Drive, Simcoe, ON , MLS #S13801282 , Image - 1

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3678 McCarthy Drive Rural Clearview, Clearview, Simcoe, ON MLS® S13801282

Residential Freehold (Vacant Land)

$270000.0
Discover the perfect blend of privacy, space, and convenience with this beautiful 1-acre property, an ideal canvas for building your dream home. Nestl
37 Photos
Last Updated : 55 Days ago
246 Penetanguishene Road, Simcoe, ON , MLS #S13801150 , Image - 1

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Unit-13, 246 Penetanguishene Road Georgian Drive, Barrie, Simcoe, ON MLS® S13801150

Residential Condo & Other (Condo Townhouse)

$425000.0
  • 4 Beds
  • 4 Baths
  • 1200-1399 sq-ft
Welcome to 246 Penetanguishene Road, Unit 13! This spacious newly renovated 4-bedroom, 4-bathroom home offers a bright, open-concept layout with gener
7 Photos
Last Updated : 55 Days ago
12A Ottaway Avenue, Simcoe, ON , MLS #S13797064 , Image - 1

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12A Ottaway Avenue Wellington, Barrie, Simcoe, ON MLS® S13797064

Residential Freehold (Vacant Land)

$399900.0
ATTENTION INVESTORS!!! Barrie just announced 50% DC fee reduction. Calling all builders, investors, and future homeowners! This 33' x 141' permit-read
6 Photos
Last Updated : 55 Days ago
12B Ottaway Avenue, Simcoe, ON , MLS #S13797042 , Image - 1

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12B Ottaway Avenue Wellington, Barrie, Simcoe, ON MLS® S13797042

Residential Freehold (Vacant Land)

$399900.0
ATTENTION INVESTORS!!! Barrie just announced 50% DC fee reduction. Calling all builders, investors, and future homeowners! This 33' x 141' permit-read
25 Photos
Last Updated : 55 Days ago
40 Mulligan Lane, Simcoe, ON , MLS #S13796508 , Image - 1

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Unit-208, 40 Mulligan Lane Wasaga Beach, Simcoe, ON MLS® S13796508

Residential Condo & Other (Condo Apartment)

$375000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to this bright and spacious 2 bedroom, 2 bath end-unit condo located in the sought-after Marlwood Golf Course community. With extra windows an
3 Photos
Last Updated : 55 Days ago
Part Lot 32 Mighton Court, Simcoe, ON , MLS #S13796478 , Image - 1
Part Lot 32 Mighton Court Rural Clearview, Clearview, Simcoe, ON MLS® S13796478

Residential Freehold (Vacant Land)

$99900.0
Investment opportunity for this Future potential building lot. This land was once two lots and merged together. If services become available it has th
31 Photos
Last Updated : 56 Days ago
9 Harbour Street, Simcoe, ON , MLS #S13794028 , Image - 1

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Unit-6112/6114, 9 Harbour Street Collingwood, Simcoe, ON MLS® S13794028

Residential Condo & Other (Condo Apartment)

$21000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Discover Fractional Ownership At Living Waters Resort With This Turnkey 1/17th Share, Offering Three Annual Vacation Weeks Including Weeks 11, 12, And
18 Photos
Last Updated : 56 Days ago
161 Wellington Street E, Simcoe, ON , MLS #N13786068 , Image - 1

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Unit-304, 161 Wellington Street E Alliston, New Tecumseth, Simcoe, ON MLS® N13786068

Residential Condo & Other (Condo Apartment)

$438000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to this beautifully designed one bedroom, one bathroom condo offering modern comfort in a highly desirable Alliston location. Featuring a brig
23 Photos
Last Updated : 56 Days ago
590 Tenth Street, Simcoe, ON , MLS #S13736530 , Image - 1

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590 Tenth Street Collingwood, Simcoe, ON MLS® S13736530

Residential Condo & Other (Condo Townhouse)

$340000.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Townhouse style condo with it's own yard in the heart of Collingwood. An open concept main floor living area awaits with ceramic and laminate flooring
50 Photos
Last Updated : 56 Days ago
8 Dunn Avenue, Simcoe, ON , MLS #S13791572 , Image - 1

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8 Dunn Avenue Orillia, Simcoe, ON MLS® S13791572

Residential Freehold (Detached)

$459900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
This charming West Ward bungalow is proof that great things come in small packages! Set on a surprisingly deep, private lot surrounded by mature trees
7 Photos
Last Updated : 56 Days ago
12 Victoria Street, Simcoe, ON , MLS #N13776396 , Image - 1

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12 Victoria Street Cookstown, Innisfil, Simcoe, ON MLS® N13776396

Residential Freehold (Vacant Land)

$399900.0
Vacant lot in the heart of Cookstown! An exciting opportunity with endless possibilities. Build your own custom home or explore the potential to acqui
5 Photos
Last Updated : 57 Days ago
6087 Sheba Drive, Simcoe, ON , MLS #S13790446 , Image - 1
6087 Sheba Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13790446

Residential Freehold (Vacant Land)

$245000.0
This gorgeous piece of land is ready for you. The 101.61 ft. x 300 ft. lot (approximately 30,000 sq. ft.) is just minutes to Lake St. John, the airpor
1 Photos
Last Updated : 57 Days ago
548 Fifth Avenue, Simcoe, ON
Unit-Lot 86, 548 Fifth Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13720338

Residential Freehold (Vacant Land)

$79969.0
Vacant land property spans 56x112 feet, providing a spacious area for designing and building a dream home or cottage retreat. The lot is elevated, off
18 Photos
Last Updated : 57 Days ago
LT 25 Leonard Road, Simcoe, ON , MLS #S13219168 , Image - 1

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LT 25 Leonard Road Rural Tiny, Tiny, Simcoe, ON MLS® S13219168

Residential Freehold (Vacant Land)

$165000.0
price drop iconPrice drop by 8.3%
Build your dream home in the sought-after Thunder Beach community on Georgian Bay. This treed corner lot sits within an established subdivision on a q
30 Photos
Last Updated : 57 Days ago
10 Pilon Road, Simcoe, ON , MLS #S13788356 , Image - 1

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10 Pilon Road Rural Tiny, Tiny, Simcoe, ON MLS® S13788356

Residential Freehold (Detached)

$349900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to your serene Georgian Bay escape! Situated on a desirable corner lot in a quiet, tree-lined pocket of Balm Beach, 10 Pilon Road offers the q
23 Photos
Last Updated : 57 Days ago
8 Myrtle Avenue, Simcoe, ON , MLS #S13788312 , Image - 1

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8 Myrtle Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13788312

Residential Freehold (Detached)

$469900.0
  • 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
26 Photos
Last Updated : 57 Days ago
346 Bay Street, Simcoe, ON , MLS #S13783804 , Image - 1

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346 Bay Street Midland, Simcoe, ON MLS® S13783804

Residential Freehold (Detached)

$499900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this charming red-brick home, where timeless character meets modern updates. Filled with warmth and personality, this home features beautif
2 Photos
Last Updated : 57 Days ago
7865 Pineridge Road, Simcoe, ON , MLS #S13732122 , Image - 1
7865 Pineridge Road Rural Ramara, Ramara, Simcoe, ON MLS® S13732122

Residential Freehold (Vacant Land)

$209900.0
Nicely treed building lot 5 minutes from Washago's Muskoka street stores and restaurants. Quiet location on dead end Road. Build your dream retreat pr
3 Photos
Last Updated : 57 Days ago
7859 Pineridge Road, Simcoe, ON , MLS #S13731928 , Image - 1
7859 Pineridge Road Rural Ramara, Ramara, Simcoe, ON MLS® S13731928

Residential Freehold (Vacant Land)

$229900.0
Build your dream home on this 1 Acre treed estate lot located at the end of a quiet road on the edge of Washago. Minutes to the LCBO, local grocery st
7 Photos
Last Updated : 57 Days ago
257 Robins Point Road, Simcoe, ON , MLS #S13785532 , Image - 1

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257 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S13785532

Residential Freehold (Vacant Land)

$289000.0
  • < 700 sq-ft
An incredible parcel of land awaits to build your dream home, perfectly situated across from the stunning shores of Georgian Bay! This lot offers peac
35 Photos
Last Updated : 58 Days ago
9 Ridge Avenue, Simcoe, ON , MLS #S13528118 , Image - 1

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9 Ridge Avenue Rural Ramara, Ramara, Simcoe, ON MLS® S13528118

Residential Freehold (Detached)

$365649.0
price drop iconPrice drop by 8.5%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Charming & Cozy Two Bedroom Home or Recreational Retreat Just Steps to Sandy Beach on Lake Simcoe Offering Great Boating and Fishing. This Affordable
35 Photos
Last Updated : 58 Days ago
87 Bond Street, Simcoe, ON , MLS #S13672502 , Image - 1

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87 Bond Street Orillia, Simcoe, ON MLS® S13672502

Residential Freehold (Detached)

$499000.0
price drop iconPrice drop by 3.9%
  • 4 +0 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Investors, contractors, handyman and families this property offers plenty of potential on a large lot 60' x 239'. House is a 1 1/2 storey approx 1442
12 Photos
Last Updated : 58 Days ago
108 Lakeshore Road E, Simcoe, ON , MLS #S13781656 , Image - 1

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108 Lakeshore Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13781656

Residential Freehold (Vacant Land)

$225000.0
Build your dream home across from the sparkling shores of Lake Simcoe! Welcome to 108 Lakeshore Road East in Oro-Medonte - a prime quarter-acre buildi
8 Photos
Last Updated : 58 Days ago
4881 Orser Street, Simcoe, ON , MLS #S13609582 , Image - 1

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4881 Orser Street Brentwood, Clearview, Simcoe, ON MLS® S13609582

Residential Freehold (Vacant Land)

$259900.0
price drop iconPrice drop by 13.3%
*Build Your Dream in the Village of Brentwood* Discover this picturesque 3.17 acre property tucked away on a quiet private dead-end road in the charmi
15 Photos
Last Updated : 58 Days ago
1419 Port Stanton Parkway, Simcoe, ON , MLS #S13780662 , Image - 1

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1419 Port Stanton Parkway Rural Severn, Severn, Simcoe, ON MLS® S13780662

Residential Freehold (Vacant Land)

$475000.0
A Unique Waterfront Property located in the Quaint Lakeside Village of Port Stanton. Build your own Cottage or Home with beautiful views of Sparrow La
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