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Houses for Sale in Simcoe Under $500K - P16

Showing results 451 - 480 of 1116
Last Updated: September 28, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
23 Photos
Last Updated : 18 Days ago
408 Veterans Drive, Simcoe, ON , MLS #S13759910 , Image - 1
Image With Blur overlay

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Unit-1, 408 Veterans Drive Holly, Barrie, Simcoe, ON MLS® S13759910

Residential Condo & Other (Condo Apartment)

$399000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome home to this Bright, well Maintained Townhouse Style Condo In The Popular South End Location Of Holly Meadows! Move-in Ready Townhouse feature
35 Photos
Last Updated : 18 Days ago
1998 Old Barrie Road E, Simcoe, ON , MLS #S13544340 , Image - 1

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1998 Old Barrie Road E Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13544340

Residential Freehold (Detached)

$499999.0
price drop iconPrice drop by 23.0%
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Renovated Century home on approximately .6 acre lot (approx 150 FT x 175 Ft) . Kitchen has 2 islands and lots of natural light. There are three bedroo
33 Photos
Last Updated : 18 Days ago
55 Georgian Glen Drive, Simcoe, ON , MLS #S13668444 , Image - 1

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55 Georgian Glen Drive Wasaga Beach, Simcoe, ON MLS® S13668444

Residential Freehold (MobileTrailer)

$164500.0
price drop iconPrice drop by 6.0%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to your charming bungalow by the beach! This affordable home boasts 2 bedrooms, 1 bathroom, and ample parking space for 4 vehicles. With 800 s
3 Photos
Last Updated : 18 Days ago
725 Aberdeen Boulevard, Simcoe, ON , MLS #S13436118 , Image - 1
Unit-57, 725 Aberdeen Boulevard Midland, Simcoe, ON MLS® S13436118

Residential Condo & Other (Vacant Land Condo)

$27500.0
  • 0-499 sq-ft
30 Foot Marina Boat Slip. Rare opportunity to purchase a slip on beautiful GEORGIAN BAY why pay for a seasonal rental at a Marina. Can you even find 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
34 Photos
Last Updated : 18 Days ago
112 Escarpment Crescent, Simcoe, ON , MLS #S13762416 , Image - 1

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112 Escarpment Crescent Collingwood, Simcoe, ON MLS® S13762416

Residential Condo & Other (Condo Townhouse)

$429000.0
  • 4 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Tucked away at the end of a quiet footpath and surrounded by mature trees and gardens, this charming 4-Bedroom, 2-Bath end unit condo offers a peacefu
36 Photos
Last Updated : 18 Days ago
46 Osborne Street, Simcoe, ON , MLS #S12907660 , Image - 1

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46 Osborne Street Victoria Harbour, Tay, Simcoe, ON MLS® S12907660

Residential Freehold (Detached)

$449777.0
price drop iconPrice drop by 20.8%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Just Steps Away From The Water And Only 10 Minutes From Hwy 400, 46 Osborne Is The Perfect Home For Starting Out Or Downsizing. This Home Shows Beauti
1 Photos
Last Updated : 18 Days ago
239 Marshall Road, Simcoe, ON
239 Marshall Road Midland, Simcoe, ON MLS® S13761598

Residential Freehold (Vacant Land)

Price On Request
Attention Investors, Builders & Hobby Farmers! Rare opportunity to own approximately 32 acres of corner lot at 239 Marshall Dr, Midland. This property
12 Photos
Last Updated : 18 Days ago
605 Oxbow Park Drive, Simcoe, ON , MLS #S13743090 , Image - 1

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605 Oxbow Park Drive Wasaga Beach, Simcoe, ON MLS® S13743090

Residential Freehold (Detached)

$495000.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Your Wasaga Beach lifestyle starts here! This beautifully fully renovated 2-bedroom, 1-bathroom year-round home offers the perfect blend of cottage ch
27 Photos
Last Updated : 18 Days ago
493 ONTARIO Street, Simcoe, ON , MLS #S13760822 , Image - 1

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493 ONTARIO Street Collingwood, Simcoe, ON MLS® S13760822

Residential Condo & Other (Condo Townhouse)

$454900.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Million-dollar Georgian Bay views from your own oversized bay windows - at a price that makes the waterfront lifestyle finally attainable. Tucked on s
3 Photos
Last Updated : 18 Days ago
11 Brechin Crescent, Simcoe, ON , MLS #S13689190 , Image - 1
11 Brechin Crescent Moonstone, Oro-Medonte, Simcoe, ON MLS® S13689190

Residential Freehold (Vacant Land)

$224900.0
price drop iconPrice drop by 10.0%
Live where you play? Build your dream home on this exceptional 0.48-acre lot in the highly sought-after Heights of Moonstone community. Offering impre
28 Photos
Last Updated : 18 Days ago
39 Chamberlain Crescent, Simcoe, ON , MLS #S12956852 , Image - 1

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39 Chamberlain Crescent Penetanguishene, Simcoe, ON MLS® S12956852

Residential Freehold (Att/Row/Townhouse)

$495000.0
price drop iconPrice drop by 5.7%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Live the lifestyle you've earned in this beautifully maintained, low-maintenance end unit bungalow just steps from Georgian Bay in the 55+ community o
16 Photos
Last Updated : 18 Days ago
43 Ferndale Drive S, Simcoe, ON , MLS #S13717628 , Image - 1

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Unit-302, 43 Ferndale Drive S Ardagh, Barrie, Simcoe, ON MLS® S13717628

Residential Condo & Other (Condo Apartment)

$499000.0
  • 3 Beds
  • 2 Baths
  • 1400-1599 sq-ft
THIRD-FLOOR CORNER SUITE WITH NEARLY 1,500 SQ FT & TREETOP VIEWS! Southern exposure brings natural light through the suite throughout the day, with Be
47 Photos
Last Updated : 18 Days ago
681 Yonge Street, Simcoe, ON , MLS #S13759246 , Image - 1

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Unit-611, 681 Yonge Street Painswick South, Barrie, Simcoe, ON MLS® S13759246

Residential Condo & Other (Condo Apartment)

$429000.0
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
STEP INTO ELEVATED CONDO LIVING WITH THIS ELEGANTLY APPOINTED 1-BEDROOM + DEN SUITE IN THEHIGHLY SOUGHT-AFTER SOUTH DISTRICT CONDOMINIUMS. KNOWN FOR I
21 Photos
Last Updated : 18 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)

$19000.0
price drop iconPrice drop by 34.5%
  • 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
17 Photos
Last Updated : 19 Days ago
15 Lucy Street, Simcoe, ON , MLS #S13755114 , Image - 1

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15 Lucy Street Penetanguishene, Simcoe, ON MLS® S13755114

Residential Freehold (Detached)

$499900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 15 Lucy Street, a super cute, thoughtfully updated 1 1/2 storey home in the heart of Penetanguishene! Offering 3 bedrooms and 2 bathrooms,
15 Photos
Last Updated : 19 Days ago
6 Orillia Road, Simcoe, ON , MLS #S13551310 , Image - 1

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6 Orillia Road Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13551310

Residential Freehold (Vacant Land)

$475000.0
price drop iconPrice drop by 4.8%
Build your dream cottage or year-round home just steps from the shores of Lake Simcoe, yet only 90 minutes from the GTA! This quiet lot is located on
21 Photos
Last Updated : 19 Days ago
34 Dawson Drive, Simcoe, ON , MLS #S13724924 , Image - 1

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Unit-839, 34 Dawson Drive Collingwood, Simcoe, ON MLS® S13724924

Residential Condo & Other (Condo Townhouse)

$449000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome to Living Stone Resort and this spacious 2-bedroom, 2-bathroom upper-level condo offering convenient one-level living in a fantastic Collingwo
40 Photos
Last Updated : 19 Days ago
299 Cundles Road E, Simcoe, ON , MLS #S13675274 , Image - 1

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Unit-#106, 299 Cundles Road E Alliance, Barrie, Simcoe, ON MLS® S13675274

Residential Condo & Other (Condo Apartment)

$414900.0
  • 2 +1 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Prime Location! Welcome to this spacious 2+1-bedroom, 2-bathroom ground-floor condo offering 1,080 sq. ft. of comfortable, open-concept living space.
15 Photos
Last Updated : 19 Days ago
Lot 25 Champlain Road, Simcoe, ON , MLS #S13704892 , Image - 1

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Lot 25 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13704892

Residential Freehold (Vacant Land)

$128000.0
Client RemarksEnjoy lakeside living with beach access when you build your dream home or cottage . Welcome to Lot 25 Champlain Road backing on the Awen
34 Photos
Last Updated : 19 Days ago
1331 Hilltop Road, Simcoe, ON , MLS #S13515012 , Image - 1

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1331 Hilltop Road Rural Severn, Severn, Simcoe, ON MLS® S13515012

Residential Freehold (MobileTrailer)

$209900.0
price drop iconPrice drop by 4.4%
  • 2 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
Enjoy peaceful living in this well-located mobile home backing onto beautiful green space and surrounded by mature perennial gardens. Offering priv
14 Photos
Last Updated : 19 Days ago
126 Bell Farm Road, Simcoe, ON , MLS #S13757256 , Image - 1

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Unit-414, 126 Bell Farm Road Alliance, Barrie, Simcoe, ON MLS® S13757256

Residential Condo & Other (Condo Apartment)

$304900.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Nestled in the vibrant north end of Barrie, this location places every convenience at your doorstep. You are only minutes away from Georgian College,
32 Photos
Last Updated : 19 Days ago
40 Horseshoe Boulevard, Simcoe, ON , MLS #S13757232 , Image - 1

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Unit-310, 40 Horseshoe Boulevard Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13757232

Residential Condo & Other (Condo Apartment)

$439900.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Welcome to Unit 310 at 40 Horseshoe Blvd., a bright and stylish 2-bedroom, 2-bathroom corner suite overlooking the 18th hole in the heart of Horseshoe
21 Photos
Last Updated : 19 Days ago
41 Mill Street E, Simcoe, ON , MLS #N13756908 , Image - 1

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41 Mill Street E Tottenham, New Tecumseth, Simcoe, ON MLS® N13756908

Residential Freehold (Detached)

$475000.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Prime Investment Opportunity! Nestled On Large 43 x 165 Ft Lot In Downtown Tottenham, Detached Home With Tons Of Potential To Rebuild Or Remodel! Awes
17 Photos
Last Updated : 19 Days ago
53 Corner Brook Trail, Simcoe, ON , MLS #N13756892 , Image - 1

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53 Corner Brook Trail Rural Innisfil, Innisfil, Simcoe, ON MLS® N13756892

Residential Freehold (Detached)

$249900.0
  • 2 Beds
  • 1 Baths
  • 1100-1500 sq-ft
LOW MAINTENANCE BUNGALOW WITH PRIVATE TREED BACKYARD, RECENT UPDATES & VIBRANT ADULT COMMUNITY LIFESTYLE! Enjoy your golden years at 53 Corner Brook T
25 Photos
Last Updated : 19 Days ago
163 Edgehill Drive, Simcoe, ON , MLS #S13756636 , Image - 1

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Unit-D7, 163 Edgehill Drive Letitia Heights, Barrie, Simcoe, ON MLS® S13756636

Residential Condo & Other (Condo Apartment)

$359900.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to D7-163 Edgehill Drive, Barrie. Fully renovated from top to bottom within the past year, this move-in-ready condo offers exceptional value i
49 Photos
Last Updated : 19 Days ago
16 Samantha Lane, Simcoe, ON , MLS #S13727986 , Image - 1

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16 Samantha Lane Midland, Simcoe, ON MLS® S13727986

Residential Condo & Other (Condo Townhouse)

$449900.0
  • 2 Beds
  • 2 Baths
  • 1400-1599 sq-ft
Welcome to modern, maintenance-free living in this beautifully designed condo semi-detached home built in 2020! With everything - from the structure t
14 Photos
Last Updated : 19 Days ago
93 Bond Street, Simcoe, ON , MLS #S13752114 , Image - 1

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93 Bond Street Orillia, Simcoe, ON MLS® S13752114

Residential Freehold (Detached)

$399900.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
COZY BUNGALOW WITH TASTEFUL FINISHES ON A 239-FT-DEEP LOT, A DETACHED OUTBUILDING & A PRIME ORILLIA LOCATION! The backyard stretches far beyond the ho
48 Photos
Last Updated : 19 Days ago
449 Mosley Street, Simcoe, ON , MLS #S13755492 , Image - 1

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449 Mosley Street Wasaga Beach, Simcoe, ON MLS® S13755492

Residential Freehold (Detached)

$469000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Incredible Value In The Heart Of Wasaga Beach! Whether You're Looking For A Year-Round Home, Weekend Getaway Or Investment Property, This 3-Bedroom, 2
26 Photos
Last Updated : 19 Days ago
3322 Pleasant Road, Simcoe, ON , MLS #S13111484 , Image - 1

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3322 Pleasant Road Rural Severn, Severn, Simcoe, ON MLS® S13111484

Residential Freehold (Detached)

$394900.0
price drop iconPrice drop by 1.3%
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Exceptional Location Near Lake Couchiching; Just 200 yards from Lake Couchiching with convenient public access, this beautifully updated home offers t
42 Photos
Last Updated : 19 Days ago
47 CABIN Crescent, Simcoe, ON , MLS #S13750686 , Image - 1

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47 CABIN Crescent Wasaga Beach, Simcoe, ON MLS® S13750686

Residential Freehold (Detached)

$432500.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Year-Round Living on the Pond in Wasaga CountryLife! Welcome to this inviting 3-bedroom, 1,084 sq. ft. cottage in Wasaga CountryLife, beautifully situ
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