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Houses for Sale in Simcoe Under $5 Million - P23

Showing results 661 - 690 of 2271
Last Updated: December 16, 2025
  • New Listings
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  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
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42 Photos
Last Updated : 39 Days ago
6 Brandy Lane Drive, Simcoe, ON , MLS #S12062420 , Image - 1
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Unit-308, 6 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S12062420

Residential Condo & Other (Condo Apartment)

$579000.0
price drop iconPrice drop by 2.7%
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Perfect as a weekend retreat or permanent home in the desirable Wyldewood development! Beautifully designed 3 bedroom, 2 bathroom end unit with open
20 Photos
Last Updated : 39 Days ago
381 Zoo Park Road, Simcoe, ON , MLS #S12248445 , Image - 1

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381 Zoo Park Road Wasaga Beach, Simcoe, ON MLS® S12248445

Residential Freehold (Detached)

$629000.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Sunny Beachy Wasaga Beach Bungalow! Ideally located in the heart of Wasaga Beach, this elevated bungalow combines comfort, charm, and convenience. Set
24 Photos
Last Updated : 39 Days ago
1589 Angus Street, Simcoe, ON , MLS #N12397396 , Image - 1

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1589 Angus Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N12397396

Residential Freehold (Detached)

$1090000.0
price drop iconPrice drop by 12.8%
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome To Luxury And Comfort In The Heart Of Innisfil! This Stunning Brick And Stone Detached Home Sits Proudly On A Premium Corner Lot In The Highly
7 Photos
Last Updated : 39 Days ago
400 Newton Street, Simcoe, ON , MLS #S12520952 , Image - 1

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400 Newton Street Victoria Harbour, Tay, Simcoe, ON MLS® S12520952

Residential Freehold (Vacant Land)

$1499000.0
Draft site plan has been agreed to by the municipality for the construction of 86 units in 11 buildings as well as a common room/office building. Draf
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
50 Photos
Last Updated : 39 Days ago
331 MARINERS Way, Simcoe, ON , MLS #S12520826 , Image - 1

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331 MARINERS Way Collingwood, Simcoe, ON MLS® S12520826

Residential Condo & Other (Condo Apartment)

$499900.0
  • 2 +0 Beds
  • 2 Baths
  • 800-899 sq-ft
This 2 bedroom, 2 bathroom, 2nd floor unit has gorgeous forest\landscape views out of the primary suite and living area. An open and bright livingroom
47 Photos
Last Updated : 39 Days ago
123 Imperial Crescent, Simcoe, ON , MLS #N12483433 , Image - 1

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123 Imperial Crescent Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12483433

Residential Freehold (Detached)

$1199900.0
  • 3 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
HUNDREDS OF THOUSANDS IN CUSTOM RENOVATIONS - TOP TO BOTTOM WITH APPRXIMATELY 3000 Sq/Ft OFLIVING SPACE! You Will Not Find Another Home Cared For With
24 Photos
Last Updated : 39 Days ago
13 Cheltenham Road, Simcoe, ON , MLS #S12494676 , Image - 1

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Unit-2, 13 Cheltenham Road Georgian Drive, Barrie, Simcoe, ON MLS® S12494676

Residential Condo & Other (Condo Townhouse)

$469999.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome Home! This Beautifully Updated and Maintained 2 Story Stacked Town Home Screams Pride of Ownership. This Home Nestled in a Quiet Friendly Comm
43 Photos
Last Updated : 39 Days ago
10 MUSQUAKE Court, Simcoe, ON , MLS #S12519248 , Image - 1

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10 MUSQUAKE Court Rural Tiny, Tiny, Simcoe, ON MLS® S12519248

Residential Freehold (Detached)

$824500.0
  • 4 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
**You'll want to keep a spare set of keys for the kids and grandkids - because once they experience this lifestyle, they'll be visiting often.** Charm
40 Photos
Last Updated : 40 Days ago
1988 River Road W, Simcoe, ON , MLS #S12519480 , Image - 1

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1988 River Road W Wasaga Beach, Simcoe, ON MLS® S12519480

Residential Freehold (Detached)

$689000.0
  • 2 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
A rare opportunity to own 100 ft of private waterfront on the tranquil Nottawasaga River, offering true four-season living and exceptional value. Set
34 Photos
Last Updated : 40 Days ago
16 Mundy Avenue, Simcoe, ON , MLS #S12518184 , Image - 1

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16 Mundy Avenue Rural Tiny, Tiny, Simcoe, ON MLS® S12518184

Residential Freehold (Detached)

$739900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
You will love this warm and inviting turn key bungalow situated close to Farlain Lake, an idyllic inland lake perfect for swimming, kayaking and fishi
26 Photos
Last Updated : 40 Days ago
15 Ravenscraig Place, Simcoe, ON , MLS #N12313943 , Image - 1

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15 Ravenscraig Place Cookstown, Innisfil, Simcoe, ON MLS® N12313943

Residential Freehold (Att/Row/Townhouse)

$789000.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 15 Ravenscraig Place, a gorgeous, brand-new end-unit townhome nestled in the heart of Cookstown, offering the perfect blend of style, comfo
20 Photos
Last Updated : 40 Days ago
49 Ridgeway Avenue, Simcoe, ON , MLS #S12516414 , Image - 1

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49 Ridgeway Avenue Allandale Heights, Barrie, Simcoe, ON MLS® S12516414

Residential Freehold (Detached)

$749000.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 49 Ridgeway Avenue A Stylish, Upgraded Backsplit in One of Barrie's Most Sought-After Neighborhoods. Nestled on a quiet, tree-lined street
10 Photos
Last Updated : 40 Days ago
56 Lakeside Terrace, Simcoe, ON , MLS #S12470113 , Image - 1

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Unit-604, 56 Lakeside Terrace Little Lake, Barrie, Simcoe, ON MLS® S12470113

Residential Condo & Other (Condo Apartment)

$389900.0
  • 1 +1 Beds
  • 1 Baths
  • 500-599 sq-ft
Welcome to your dream condo with stunning views of the lake! This well-designed unit offers picturesque lake views from the master bedroom, living roo
37 Photos
Last Updated : 40 Days ago
31 Desroches Trail, Simcoe, ON , MLS #S12515852 , Image - 1

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31 Desroches Trail Rural Tiny, Tiny, Simcoe, ON MLS® S12515852

Residential Freehold (Detached)

$545500.0
  • 2 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Offered for the first time, this charming year-round home or cottage captures the timeless appeal of Lafontaine living. Tucked away on a quiet street
13 Photos
Last Updated : 41 Days ago
265 Barrie Road, Simcoe, ON , MLS #S12514850 , Image - 1

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265 Barrie Road Orillia, Simcoe, ON MLS® S12514850

Residential Freehold (Multiplex)

$1098000.0
  • 10 Beds
  • 5 Baths
  • 3500-5000 sq-ft
This charming 5-unit multiplex in the heart of Orillia is an excellent opportunity for a seasoned investor grow their portfolio or a new investor look
34 Photos
Last Updated : 41 Days ago
212 Maplewood Drive, Simcoe, ON , MLS #N12514836 , Image - 1

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212 Maplewood Drive Angus, Essa, Simcoe, ON MLS® N12514836

Residential Freehold (Detached)

$773000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this beautiful 3-bedroom, 3-bathroom home offering just over 2,300 sq. ft. of finished living space on a desirable corner lot. This propert
35 Photos
Last Updated : 41 Days ago
8 Pridham Court, Simcoe, ON , MLS #S12514698 , Image - 1

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8 Pridham Court Wasaga Beach, Simcoe, ON MLS® S12514698

Residential Freehold (Detached)

$859777.0
  • 2 +2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to this exceptional raised bungalow, perfectly situated on an estate-sized lot backing onto a serene ravine. Tucked away on a quiet cul-de-sac
13 Photos
Last Updated : 41 Days ago
1102 Horseshoe Valley Road W, Simcoe, ON , MLS #S12451947 , Image - 1

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Unit-114, 1102 Horseshoe Valley Road W Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12451947

Residential Condo & Other (Condo Apartment)

$351000.0
price drop iconPrice drop by 2.2%
  • 1 Beds
  • 1 Baths
  • 500-599 sq-ft
Cozy Condo Retreat in he Hear of Horseshoe Valley! Experience four seasons of adventure with charming 1-bedroom ground-floor condo, ideally located ju
30 Photos
Last Updated : 41 Days ago
22 Grace Crescent, Simcoe, ON , MLS #S12473057 , Image - 1

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22 Grace Crescent Painswick South, Barrie, Simcoe, ON MLS® S12473057

Residential Freehold (Detached)

$815000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome 22 Grace Crescent in the desirable Painswick South community of Barrie. There is so much to love about this home starting with the location. L
45 Photos
Last Updated : 41 Days ago
46 Tyndale Road, Simcoe, ON , MLS #S12391716 , Image - 1

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46 Tyndale Road South Shore, Barrie, Simcoe, ON MLS® S12391716

Residential Freehold (Detached)

$1999000.0
  • 5 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Experience Unrivaled Luxury in Tollendal's Premier EnclaveStep into the lap of luxury with this stunning, custom-built home in the coveted Tollendal a
14 Photos
Last Updated : 41 Days ago
267 Barrie Road, Simcoe, ON , MLS #S12456852 , Image - 1

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267 Barrie Road Orillia, Simcoe, ON MLS® S12456852

Residential Freehold (Vacant Land)

$275000.0
  • 9 Beds
  • < 700 sq-ft
Vacant Land FOR SALE! **SELLER FINANCING AVAILABLE** Fantastic Opportunity: Build A TRIPLEX On A Huge 1/4 Acre Lot. Great For Multi-Generational Famil
11 Photos
Last Updated : 41 Days ago
909B Willow Street, Simcoe, ON , MLS #N12513916 , Image - 1

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909B Willow Street Lefroy, Innisfil, Simcoe, ON MLS® N12513916

Residential Freehold (Vacant Land)

$209000.0
  • < 700 sq-ft
Great opportunity to build your own home or home away from home in lovely Lefroy. Also suitable for small builders/investors. Great location, a short
37 Photos
Last Updated : 41 Days ago
60 Carley Crescent, Simcoe, ON , MLS #S12418114 , Image - 1

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60 Carley Crescent Painswick South, Barrie, Simcoe, ON MLS® S12418114

Residential Freehold (Detached)

$899900.0
price drop iconPrice drop by 5.2%
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to this beautifully cared for all-brick family home, offering 2,688 sq. ft. on a quiet crescent in one of Barries most desirable neighborhoods
10 Photos
Last Updated : 41 Days ago
29 Rue Camille Road, Simcoe, ON , MLS #S12462687 , Image - 1

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29 Rue Camille Road Rural Tiny, Tiny, Simcoe, ON MLS® S12462687

Residential Freehold (Detached)

$849000.0
price drop iconPrice drop by 2.3%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
This newish home offers 1700+ square feet of finished living space, and is located in Tiny Township's western shoreline area. Short stroll to Cove Bea
27 Photos
Last Updated : 41 Days ago
657 Manly Street, Simcoe, ON , MLS #S12512356 , Image - 1

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657 Manly Street Midland, Simcoe, ON MLS® S12512356

Residential Freehold (Detached)

$665000.0
  • 3 Beds
  • 1 Baths
  • 1500-2000 sq-ft
Welcome home to this well maintained home on a large, centrally located in town lot. There are no steps on this main floor including to the separate f
20 Photos
Last Updated : 41 Days ago
934 Gilmore Avenue, Simcoe, ON , MLS #N12512196 , Image - 1

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934 Gilmore Avenue Lefroy, Innisfil, Simcoe, ON MLS® N12512196

Residential Freehold (Detached)

$569900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Charming Brick Bungalow with a basement in the Heart of Lefroy. Ready to roll up your sleeves or bring your contractor? This property is bursting with
28 Photos
Last Updated : 41 Days ago
13 Eberhardt Drive, Simcoe, ON , MLS #S12444057 , Image - 1

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13 Eberhardt Drive Wasaga Beach, Simcoe, ON MLS® S12444057

Residential Freehold (Att/Row/Townhouse)

$720000.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 13 Eberhardt Dr, Wasaga Beach a RARE opportunity to Own a beautifully designedModern 4-bedroom, 4-washroom, Double Car Garage executive END
50 Photos
Last Updated : 41 Days ago
18 Cypress Point Street, Simcoe, ON , MLS #S12472026 , Image - 1

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18 Cypress Point Street Ardagh, Barrie, Simcoe, ON MLS® S12472026

Residential Freehold (Detached)

$1099999.0
price drop iconPrice drop by 2.6%
  • 3 Beds
  • 3 Baths
  • 2000-2500 sq-ft
WELCOME to 18 Cypress Point Street located within a small enclave of homes in one of Barrie's newer communities - Pineview Greens Estates. This well-a
40 Photos
Last Updated : 41 Days ago
4 Linden Lane, Simcoe, ON , MLS #N12477581 , Image - 1

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4 Linden Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N12477581

Residential Freehold (Detached)

$329900.0
price drop iconPrice drop by 5.7%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome Home! This Beautiful Monaco Style One Level Land Lease Home in the Adult Lifestyle Community of Sandy Cove Acres is Almost 1400 sq ft and is B
39 Photos
Last Updated : 41 Days ago
57 Highland Drive, Simcoe, ON , MLS #S12511204 , Image - 1

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57 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S12511204

Residential Freehold (Detached)

$1270000.0
  • 3 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to this beautifully crafted family home, located in one of Horseshoe Valley's most prestigious and sought-after executive neighbourhoods. Offe
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