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Houses for Sale in Simcoe Under $500K - P35

Showing results 1021 - 1050 of 1093
Last Updated: August 13, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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5 Photos
Last Updated : 111 Days ago
81 Polish Avenue, Simcoe, ON , MLS #S13043332 , Image - 1
81 Polish Avenue Penetanguishene, Simcoe, ON MLS® S13043332

Residential Freehold (Vacant Land)

$129900.0
Welcome to Polish Avenue in Penetanguishene. An exceptional opportunity to build your dream home on this vacant lot! Located in a desirable and establ
12 Photos
Last Updated : 111 Days ago
Lot 438 Champlain Road, Simcoe, ON , MLS #S12949244 , Image - 1

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Lot 438 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S12949244

Residential Freehold (Vacant Land)

$299000.0
220 feet of frontage on a double lot steps to a sandy beach and almost three quarters of an acre in size - This is an incredibly rare opportunity to b
38 Photos
Last Updated : 111 Days ago
40 Horseshoe Boulevard, Simcoe, ON , MLS #S12501128 , Image - 1

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Unit-416, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12501128

Residential Condo & Other (Condo Apartment)

$359000.0
  • 1 Beds
  • 1 Baths
  • 500-599 sq-ft
Year Round Entertainment & Relaxation in the Heart of Horseshoe Valley Resort. This Cozy, Upgraded 1 Bed 1 Bath has the Perfect Blend of Modern Amenit
10 Photos
Last Updated : 111 Days ago
19 Bourgeois Beach Road, Simcoe, ON , MLS #S13039310 , Image - 1

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19 Bourgeois Beach Road Victoria Harbour, Tay, Simcoe, ON MLS® S13039310

Residential Freehold (Vacant Land)

$224900.0
Top 5 Reasons You Will Love This Property: 1) Sought-after location just moments from Georgian Bay, offering effortless access to boating, kayaking, a
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
21 Photos
Last Updated : 111 Days ago
9 Harbour Street E, Simcoe, ON , MLS #S13037230 , Image - 1

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Unit-2307, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S13037230

Residential Condo & Other (Timeshare)

$29000.0
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
An exceptional opportunity to own a fractional interest in a condo at Living Water Resort. Enjoy a vacation lifestyle in Collingwood with three design
40 Photos
Last Updated : 112 Days ago
56 Birch Trail, Simcoe, ON , MLS #S13036556 , Image - 1

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56 Birch Trail Wasaga Beach, Simcoe, ON MLS® S13036556

Residential Freehold (Detached)

$499777.0
  • 1 Beds
  • 2 Baths
  • < 700 sq-ft
Charming A-Frame Cottage Just a 9-Minute Walk from Allenwood Beach. Nestled at the end of a tranquil cul-de-sac, this delightful A-frame cottage is on
34 Photos
Last Updated : 112 Days ago
90 Dean Avenue, Simcoe, ON , MLS #S9231440 , Image - 1

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Unit-507, 90 Dean Avenue Painswick South, Barrie, Simcoe, ON MLS® S9231440

Residential Condo & Other (Leasehold Condo)

$419900.0
price drop iconPrice drop by 7.7%
  • 1 Beds
  • 2 Baths
  • 900-999 sq-ft
The Terraces of Heritage Square is a Adult over 60+ building. These buildings have lots to offer, Party rooms, library, computer room and a second lev
20 Photos
Last Updated : 113 Days ago
16 Westbury Road, Simcoe, ON , MLS #S13031762 , Image - 1

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Unit-202, 16 Westbury Road Wasaga Beach, Simcoe, ON MLS® S13031762

Residential Condo & Other (Condo Apartment)

$399900.0
  • 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
35 Photos
Last Updated : 113 Days ago
244 Penetanguishene Road, Simcoe, ON , MLS #S13029632 , Image - 1

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Unit-11, 244 Penetanguishene Road Georgian Drive, Barrie, Simcoe, ON MLS® S13029632

Residential Condo & Other (Condo Townhouse)

$399000.0
  • 4 Beds
  • 4 Baths
  • 1000-1199 sq-ft
Amazing and Spacious 4-Bedroom, 4-Bathroom Condo Townhouse in Barrie's Sought-After Georgian Drive Community! Welcome to this bright and spacious cond
5 Photos
Last Updated : 114 Days ago
Lot 6 Rue Eric Street, Simcoe, ON , MLS #S13027894 , Image - 1
Lot 6 Rue Eric Street Lafontaine, Tiny, Simcoe, ON MLS® S13027894

Residential Freehold (Vacant Land)

$324900.0
  • < 700 sq-ft
This expansive 1.4-acre residential lot is the perfect canvas for your dream home! HR Zoning offers the ability to accommodate multi-generational livi
5 Photos
Last Updated : 114 Days ago
Lot 33 Macavalley Road, Simcoe, ON , MLS #S13024542 , Image - 1
Lot 33 Macavalley Road Rural Tiny, Tiny, Simcoe, ON MLS® S13024542

Residential Freehold (Vacant Land)

$499777.0
Build your dream home on this prime 20-acre parcel, ideally located on Macavalley Road in Tiny. Offering a great opportunity for those looking to crea
5 Photos
Last Updated : 115 Days ago
7816 Riverleigh Drive, Simcoe, ON , MLS #S12998942 , Image - 1
7816 Riverleigh Drive Rural Ramara, Ramara, Simcoe, ON MLS® S12998942

Residential Freehold (Vacant Land)

$250000.0
This vacant riverfront lot in the town of Washago, along the Green River, offers direct access to peaceful waters and is a gateway to endless outdoor
6 Photos
Last Updated : 118 Days ago
14 Barbara Avenue, Simcoe, ON , MLS #S13010966 , Image - 1

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14 Barbara Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13010966

Residential Freehold (Vacant Land)

$344000.0
  • < 700 sq-ft
Here's an Easy Choice.With an ideal location, a level ready-to-build residential lot, development charges paid (approx. $41,245 value), two driveways,
5 Photos
Last Updated : 119 Days ago
309 Penetanguishene Road, Simcoe, ON , MLS #S12876860 , Image - 1
309 Penetanguishene Road Midland, Simcoe, ON MLS® S12876860

Residential Freehold (Vacant Land)

$275000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a infill lot, close to hospital, schools
5 Photos
Last Updated : 119 Days ago
305 Penetanguishene Rd Road, Simcoe, ON , MLS #S12876730 , Image - 1
305 Penetanguishene Rd Road Midland, Simcoe, ON MLS® S12876730

Residential Freehold (Vacant Land)

$250000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a building lot, close to hospital, schoo
5 Photos
Last Updated : 119 Days ago
301 Penetanguishene Road, Simcoe, ON , MLS #S12876542 , Image - 1
301 Penetanguishene Road Midland, Simcoe, ON MLS® S12876542

Residential Freehold (Vacant Land)

$225000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a infill lot, close to hospital, schools
5 Photos
Last Updated : 119 Days ago
1041 Ingram Crescent, Simcoe, ON , MLS #S12876230 , Image - 1
1041 Ingram Crescent Midland, Simcoe, ON MLS® S12876230

Residential Freehold (Vacant Land)

$275000.0
Vacant land with exceptional development upside in the heart of West End Midland! Rare opportunity to acquire a building lot, close to hospital, schoo
5 Photos
Last Updated : 119 Days ago
1037 Ingram Crescent, Simcoe, ON , MLS #S12875954 , Image - 1
1037 Ingram Crescent Midland, Simcoe, ON MLS® S12875954

Residential Freehold (Vacant Land)

$300000.0
Unique deep lot ! Subject to site plan and municipal approvals, tons of flexibility for residential development under the Town of Midland's zoning fra
6 Photos
Last Updated : 119 Days ago
611 William Street, Simcoe, ON , MLS #S12875640 , Image - 1

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611 William Street Midland, Simcoe, ON MLS® S12875640

Residential Freehold (Vacant Land)

$160000.0
Requires Official Plan Act amendment from current Natural Heritage designation. Possibly a zoning change depending on development strategy. Registere
16 Photos
Last Updated : 119 Days ago
150 AMANDA Street, Simcoe, ON , MLS #S12676848 , Image - 1

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150 AMANDA Street Waubaushene, Tay, Simcoe, ON MLS® S12676848

Residential Freehold (Vacant Land)

$159900.0
Build your dream home on this exceptional corner lot, tucked away on a quiet, low-traffic street in the welcoming community of Waubaushene. Just a sho
17 Photos
Last Updated : 119 Days ago
250 Peek -a- Boo Trail, Simcoe, ON , MLS #S12472261 , Image - 1

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250 Peek -a- Boo Trail Rural Tiny, Tiny, Simcoe, ON MLS® S12472261

Residential Freehold (Vacant Land)

$389000.0
Discover the perfect opportunity to build your Dream Home or summer retreat on this beautiful partially cleared 3.5+ Acre lot, ideally located in the
15 Photos
Last Updated : 120 Days ago
5 CHIPPEWA Trail, Simcoe, ON , MLS #S13000868 , Image - 1

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5 CHIPPEWA Trail Wasaga Beach, Simcoe, ON MLS® S13000868

Residential Freehold (Modular Home)

$90000.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Escape to your ideal summer retreat at Wasaga Countrylife Resort with this pristine 2007 Northlander Cottager Classic front porch model where comfort
24 Photos
Last Updated : 120 Days ago
15 Dawson Drive, Simcoe, ON , MLS #S12999540 , Image - 1

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Unit-3, 15 Dawson Drive Collingwood, Simcoe, ON MLS® S12999540

Residential Condo & Other (Condo Townhouse)

$315000.0
  • 1 Baths
  • 0-499 sq-ft
Step into this beautifully updated second-floor corner studio condo in the heart of Collingwood perfectly designed for year round living . Just minute
25 Photos
Last Updated : 121 Days ago
4075 Airport Road, Simcoe, ON , MLS #S12493152 , Image - 1

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4075 Airport Road Rural Ramara, Ramara, Simcoe, ON MLS® S12493152

Residential Freehold (Detached)

$195000.0
price drop iconPrice drop by 2.0%
  • 1 Beds
  • 1 Baths
  • 700-1100 sq-ft
If you are searching for a large lot and are extremely handy with the desire to purchase a fixer upper and make it your own, then this is your sign! L
21 Photos
Last Updated : 121 Days ago
4067 Airport Road, Simcoe, ON , MLS #S12493910 , Image - 1

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4067 Airport Road Rural Ramara, Ramara, Simcoe, ON MLS® S12493910

Residential Freehold (Detached)

$199999.0
price drop iconPrice drop by 11.1%
  • 1 Beds
  • 1 Baths
  • 700-1100 sq-ft
Attention Investors, Developers & Handy Homeowners! Welcome to 4067 Airport Rd., Ramara - a charming one-bedroom home offering incredible potential fo
17 Photos
Last Updated : 121 Days ago
19 Birch Grove Drive, Simcoe, ON , MLS #S12995486 , Image - 1

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19 Birch Grove Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12995486

Residential Freehold (Vacant Land)

$489000.0
Have you ever dreamed of living in a place where you can walk to the tee-box or the chairlifts? Welcome to 19 Birch Grove Drive, a rare opportunity to
40 Photos
Last Updated : 121 Days ago
345 LINWOOD Avenue, Simcoe, ON , MLS #S12994782 , Image - 1

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345 LINWOOD Avenue Orillia, Simcoe, ON MLS® S12994782

Residential Freehold (Detached)

$449400.0
  • 5 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Opportunity awaits in this detached 1-storey family home located on a quiet residential street in south-central Orillia. Situated on a standard-sized
5 Photos
Last Updated : 122 Days ago
57B Coldwater Road, Simcoe, ON , MLS #S12953618 , Image - 1
57B Coldwater Road Coldwater, Severn, Simcoe, ON MLS® S12953618

Residential Freehold (Vacant Land)

$250000.0
Situated on the main street just steps from the vibrant village of Coldwater, this cleared residential/commercial lot offers just over quarter of an a
1 Photos
Last Updated : 122 Days ago
95 wellington Street, Simcoe, ON
95 wellington Street Atherley, Ramara, Simcoe, ON MLS® S12709122

Residential Freehold (Vacant Land)

$220000.0
  • < 700 sq-ft
Discover a remarkable opportunity in Ramara Township, where this expansive vacant lot awaits your imagination. With the potential to be divided into t
8 Photos
Last Updated : 124 Days ago
LT 14 9th Line, Simcoe, ON , MLS #N12986934 , Image - 1

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LT 14 9th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® N12986934

Residential Freehold (Vacant Land)

$425000.0
  • < 700 sq-ft
Build your dream home on this beautiful, flat residential lot - the perfect setting for family living. Enjoy space for kids to run, gardens to grow, a
Shortlisted Properties
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