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Houses for Sale in Simcoe Under $5 Million - P21

Showing results 601 - 630 of 4534
Last Updated: November 10, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
32 Photos
Last Updated : 4 Days ago
535 High Street N, Simcoe, ON , MLS #S14155156 , Image - 1
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535 High Street N Orillia, Simcoe, ON MLS® S14155156

Residential Freehold (Detached)

$639900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Where VINTAGE CHARM meets MODERN LUXURY - Welcome to 535 High Street - from the moment you arrive you will be captivated by the stunning curb appeal o
Open House : Sat Nov 14, 12:00 PM to 02:00 PM
1 Photos
Last Updated : 4 Days ago
4 Virgilwood Crescent, Simcoe, ON
4 Virgilwood Crescent Cundles East, Barrie, Simcoe, ON MLS® S14154686

Residential Freehold (Detached)

$629555.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Discover the fully renovated detached house with lot of $$$ spent to bring a perfect blend of space, style & convenience in this 3-level backsplit hom
1 Photos
Last Updated : 4 Days ago
232 Kozlov Street, Simcoe, ON
232 Kozlov Street West Bayfield, Barrie, Simcoe, ON MLS® S13823468

Residential Freehold (Detached)

$599000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Attention all first time home buyers, small families, and investors alike! Welcome to 232 Kozlov St, a corner-style turnkey gem in Barrie's desirable
36 Photos
Last Updated : 4 Days ago
19 Dawson Drive, Simcoe, ON , MLS #S13756960 , Image - 1

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Unit-68, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S13756960

Residential Condo & Other (Condo Townhouse)

$380000.0
  • 2 Beds
  • 2 Baths
  • 600-699 sq-ft
One-of-a-kind ground floor condo in Collingwood with incredible outdoor space that truly feels like home. You'll never tire of returning after a day
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
49 Photos
Last Updated : 4 Days ago
24 Pierce Place, Simcoe, ON , MLS #N13852320 , Image - 1

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24 Pierce Place Tottenham, New Tecumseth, Simcoe, ON MLS® N13852320

Residential Freehold (Detached)

$1375999.0
price drop iconPrice drop by 3.7%
  • 4 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Offered for the first time, 24 Pierce Place is a heavily upgraded 4-bedroom, 4-bathroom detached home in Tottenham with over 3,000 sq ft of living spa
40 Photos
Last Updated : 4 Days ago
163 Grove Street E, Simcoe, ON , MLS #S14131252 , Image - 1

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163 Grove Street E Wellington, Barrie, Simcoe, ON MLS® S14131252

Residential Freehold (Detached)

$610000.0
  • 3 +0 Beds
  • 2 Baths
  • 700-1100 sq-ft
Bold Bright & Beautiful Move In Ready Fully Detached Three Bed, Two Bath, Home on Fifty Foot Lot Across from MacMorrison Park with Separate Entrance,
49 Photos
Last Updated : 4 Days ago
6049 3rd Line, Simcoe, ON , MLS #N14136894 , Image - 1

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6049 3rd Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N14136894

Residential Freehold (Detached)

$999999.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
A RARE OPPORTUNITY THAT TRULY HAS IT ALL! INCREDIBLE 39 x 29 WORKSHOP and a LARGE 47 x 23 GARAGE WITH B/I shelves and work bench, offering conveni
26 Photos
Last Updated : 4 Days ago
36 Broadview Avenue, Simcoe, ON , MLS #S14155070 , Image - 1

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36 Broadview Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S14155070

Residential Freehold (Detached)

$599999.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to this inviting, bungalow ideally situated near beautiful Bass Lake! Offering convenient main-floor living, this home features three bedrooms
24 Photos
Last Updated : 4 Days ago
12 Tomporowski Trail, Simcoe, ON , MLS #N14100158 , Image - 1

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12 Tomporowski Trail Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N14100158

Residential Freehold (Detached)

$949000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
This detached, two-storey home offers 3 bedrooms and 3 bathrooms, with approximately 1,500-2,000 sq. ft. of living space. The home features an upgrade
50 Photos
Last Updated : 4 Days ago
24 Ramblings Way, Simcoe, ON , MLS #S14111570 , Image - 1

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24 Ramblings Way
Unit-706, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S14111570

Residential Condo & Other (Condo Apartment)

$699000.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to Bayview Tower! This lovely 3 bedroom unit on the 7th floor brings in ample natural light with large windows looking out over Blue Mountain
25 Photos
Last Updated : 4 Days ago
550 Simcoe Street, Simcoe, ON , MLS #S14149946 , Image - 1

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550 Simcoe Street Collingwood, Simcoe, ON MLS® S14149946

Residential Freehold (Detached)

$599000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
True bungalow, Perfectly situated on a quaint cul-de-sac in a sought-after central location, this charming 2-bedroom, 1-bath (in floor heat) bungalow
25 Photos
Last Updated : 4 Days ago
2157 Champlain Road, Simcoe, ON , MLS #S14154394 , Image - 1

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2157 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S14154394

Residential Freehold (Detached)

$369900.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Leave the noise of the city behind and discover this charming cottage nestled in the heart of popular Sawlog Bay in Tiny Township. Set on a private, t
24 Photos
Last Updated : 4 Days ago
444 Oxbow Crescent, Simcoe, ON , MLS #S14133942 , Image - 1

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444 Oxbow Crescent Collingwood, Simcoe, ON MLS® S14133942

Residential Condo & Other (Semi-Detached Condo)

$535000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Imagine carefree living in this beautifully updated bungalow-style home, thoughtfully designed for comfortable, low-maintenance one-level living, with
28 Photos
Last Updated : 4 Days ago
1055 Henry Street, Simcoe, ON , MLS #S14154836 , Image - 1

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1055 Henry Street Waverley, Tay, Simcoe, ON MLS® S14154836

Residential Freehold (Detached)

$948500.0
  • 5 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Unique Custom Home in Prime Waverley Location! Ideally situated between Georgian Bay, Horseshoe & Moonstone Ski Hills, Wasaga Beach, Orr Lake, and jus
12 Photos
Last Updated : 4 Days ago
167 Edgehill Drive, Simcoe, ON , MLS #S14154796 , Image - 1

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Unit-E9, 167 Edgehill Drive Letitia Heights, Barrie, Simcoe, ON MLS® S14154796

Residential Condo & Other (Condo Apartment)

$329900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
AFFORDABLE TOP-FLOOR CONDO WITH 2 BEDROOMS, A PRIVATE BALCONY, INCLUDED PARKING & AN EXCELLENT WEST BARRIE LOCATION! At 167 Edgehill Drive Unit E9, an
50 Photos
Last Updated : 4 Days ago
16 Shephard Avenue, Simcoe, ON , MLS #N14125260 , Image - 1

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16 Shephard Avenue Alliston, New Tecumseth, Simcoe, ON MLS® N14125260

Residential Freehold (Detached)

$899000.0
  • 4 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Enjoy the best of family living and nature in this immaculate 4+1 bedroom home, offering 2,338 sq. ft. of above-grade living space across four finishe
42 Photos
Last Updated : 4 Days ago
31 MCKEAN Boulevard, Simcoe, ON , MLS #S14116540 , Image - 1

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31 MCKEAN Boulevard Nottawa, Clearview, Simcoe, ON MLS® S14116540

Residential Freehold (Detached)

$1149900.0
  • 2 +2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 31 McKean Green. A raised bungalow in Nottawa on a half acre lot where the backyard is a private golf course. Built by the owner, who runs
25 Photos
Last Updated : 4 Days ago
7272 36/37 Nottawasaga Side Road E, Simcoe, ON , MLS #S14103684 , Image - 1

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7272 36/37 Nottawasaga Side Road E Rural Clearview, Clearview, Simcoe, ON MLS® S14103684

Residential Freehold (Detached)

$2399000.0
  • 4 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Set on 2.2 beautifully landscaped acres along the highly coveted 36/37 Side Road East, this charming country property is a rare blend of character, wa
34 Photos
Last Updated : 4 Days ago
8 Albert Street E, Simcoe, ON , MLS #S14126400 , Image - 1

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8 Albert Street E Hillsdale, Springwater, Simcoe, ON MLS® S14126400

Residential Freehold (Detached)

$574900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Small-Town Charm, Country Character & Room to Dream! Welcome to the quaint community of Hillsdale, where quiet streets and a relaxed pace of life make
47 Photos
Last Updated : 4 Days ago
40 Centre Street, Simcoe, ON , MLS #N14154310 , Image - 1

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40 Centre Street Angus, Essa, Simcoe, ON MLS® N14154310

Residential Freehold (Semi-Detached )

$572777.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Small but mighty, this beautifully updated semi-detached home packs an incredible punch with lovely updated features! The main floor offers a bright,
50 Photos
Last Updated : 4 Days ago
84 Culbert Road, Simcoe, ON , MLS #N14152044 , Image - 1

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84 Culbert Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N14152044

Residential Freehold (Detached)

$1498000.0
  • 4 Beds
  • 5 Baths
  • 3000-3500 sq-ft
This beautiful corner-lot house is a must-see! Located in the heart of the friendly, family-oriented Summerlyn Village community, it features a bright
33 Photos
Last Updated : 4 Days ago
241 Donalda Street, Simcoe, ON , MLS #S13460042 , Image - 1

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241 Donalda Street Midland, Simcoe, ON MLS® S13460042

Residential Freehold (Detached)

$539777.0
price drop iconPrice drop by 1.8%
  • 2 +0 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 241 Donalda Street in Midland, a cute and cozy home that is perfect for first-time buyers, downsizers, or anyone looking for a well-located
38 Photos
Last Updated : 4 Days ago
12 Illinois Crescent, Simcoe, ON , MLS #S13722168 , Image - 1

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12 Illinois Crescent Wasaga Beach, Simcoe, ON MLS® S13722168

Residential Freehold (Detached)

$635000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
You'll be wow'd from entry to exit in this fully renovated 1488 sq ft bungalow in Park Place, a high demand 55+ community in Wasaga Beach. Entering t
17 Photos
Last Updated : 4 Days ago
25 Lions Gate Boulevard, Simcoe, ON , MLS #S13664570 , Image - 1

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25 Lions Gate Boulevard Little Lake, Barrie, Simcoe, ON MLS® S13664570

Residential Freehold (Att/Row/Townhouse)

$474900.0
price drop iconPrice drop by 7.9%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
954 sq/ft. 2-bedroom townhouse located just off Livingston Street. A good family home or starter home featuring two bedrooms and a 4-piece bathroom on
41 Photos
Last Updated : 4 Days ago
62 Season Crescent, Simcoe, ON , MLS #S14154374 , Image - 1

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62 Season Crescent Wasaga Beach, Simcoe, ON MLS® S14154374

Residential Freehold (Detached)

$698000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
EXCEPTIONAL HOME ON ONE OF THE LARGEST LOTS IN THE NEIGHBOURHOOD! Welcome to this stunning, newly built two-storey home in the heart of Wasaga Beach,
42 Photos
Last Updated : 4 Days ago
152 Greer Street, Simcoe, ON , MLS #S13757912 , Image - 1

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152 Greer Street Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13757912

Residential Freehold (Att/Row/Townhouse)

$759900.0
price drop iconPrice drop by 4.1%
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
2-year-old, 1985 sqft townhouse at 152 GREER ST, featuring many premium builder upgrades and 9 ft. ceilings on the main floor. The chef-inspired kitch
16 Photos
Last Updated : 4 Days ago
90 Highland Drive, Simcoe, ON , MLS #S14029628 , Image - 1

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Unit-2290, 90 Highland Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14029628

Residential Condo & Other (Condo Apartment)

$388500.0
  • 2 +2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Unique Two-Unit Condominium in Horseshoe Valley - 90 Highland Drive is an exceptional opportunity for investors or homeowners looking to generate rent
26 Photos
Last Updated : 4 Days ago
76 Linden Lane, Simcoe, ON , MLS #N14105410 , Image - 1

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76 Linden Lane Alcona, Innisfil, Simcoe, ON MLS® N14105410

Residential Freehold (Detached)

$399900.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
PRICED TO SELL! BRAND-NEW, MOVE-IN READY & IMMEDIATE OCCUPANCY AVAILABLE! Why buy an older renovated home when you can own brand-new? Discover excepti
18 Photos
Last Updated : 4 Days ago
97 Warman Street, Simcoe, ON , MLS #N14032374 , Image - 1

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97 Warman Street Alliston, New Tecumseth, Simcoe, ON MLS® N14032374

Residential Freehold (Detached)

$759900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this spacious four-bedroom detached home offering 2,468 sq. ft. of finished above-grade living space, with an unfinished basement providin
50 Photos
Last Updated : 4 Days ago
39 Landscape Drive, Simcoe, ON , MLS #S14027460 , Image - 1

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39 Landscape Drive Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S14027460

Residential Freehold (Detached)

$989000.0
  • 2 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Ready for your next chapter? Discover the perfect blend of comfort, elegance and easy living at 39 Landscape Drive in the sought after Horseshoe Valle
Shortlisted Properties
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