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Houses for Sale in Collingwood ON Under $500K

Showing results 1 - 30 of 74

Are you looking for houses under $500k for sale in Collingwood ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Collingwood. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Collingwood. Whether you’re looking to buy houses under under $500k in Collingwood ON for residential living or as investment opportunities, our listings allow you to filter by amenities, property age, number of bedrooms and much more. Explore a diverse range of Collingwood houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: November 12, 2026

27 Photos

460 Ontario Street, Simcoe, ON , MLS #S14174806 , Image - 1

Unit-209, 460 Ontario Street Collingwood, Simcoe, ON MLS® S14174806

Residential Condo & Other (Condo Apartment)

$359000.0

2 Beds
1 Baths
700-799 sq-ft

Experience effortless, turnkey living in this updated two-bedroom condominium at Bayview Terrace.This bright open-concept interior features fresh neut

12 Photos

467 Ontario Street, Simcoe, ON , MLS #S13880330 , Image - 1

467 Ontario Street Collingwood, Simcoe, ON MLS® S13880330

Residential Condo & Other (Condo Townhouse)

$279000.0

Price drop by 11.4%

3 Beds
2 Baths
1400-1599 sq-ft

Opportunity for Investors, Contractors and Renovators! Located in Collingate Mews, this three-bedroom townhouse condominium offers approximately 1,425

37 Photos

711 Johnston Park Avenue, Simcoe, ON , MLS #S13836746 , Image - 1

711 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13836746

Residential Condo & Other (Condo Townhouse)

$449900.0

2 Beds
2 Baths
1000-1199 sq-ft

SUN, SAND, SLOPES and MORE! Live the four-season lifestyle you've been dreaming of - whether your days are filled with relaxing at the private beach,

24 Photos

19 Dawson Drive, Simcoe, ON , MLS #S14171026 , Image - 1

Unit-42, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S14171026

Residential Condo & Other (Condo Apartment)

$354900.0

2 Beds
2 Baths
700-799 sq-ft

Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in an ideal Collingwood location. Freshly painted throughout with new vinyl laminate f

29 Photos

1 CHAMBERLAIN Crescent, Simcoe, ON , MLS #S14170436 , Image - 1

Unit-109, 1 CHAMBERLAIN Crescent Collingwood, Simcoe, ON MLS® S14170436

Residential Condo & Other (Condo Townhouse)

$479000.0

2 Beds
1 Baths
900-999 sq-ft

GROUND FLOOR END UNIT | 10-FT CEILINGS | CONVENIENT SECONDARY BUILDING ACCESS ~~ Welcome to Dwell at Creekside, a desirable three-storey condominium c

17 Photos

34 Dawson Drive, Simcoe, ON , MLS #S13793238 , Image - 1

Unit-825, 34 Dawson Drive Collingwood, Simcoe, ON MLS® S13793238

Residential Condo & Other (Condo Townhouse)

$399000.0

2 Beds
2 Baths
1200-1399 sq-ft

Exceptional Value in Collingwood! Offered at just $399,000, this unique upper-level condo at 34 Dawson Drive, Unit 825 offers a versatile layout and a

31 Photos

214 Escarpment Crescent, Simcoe, ON , MLS #S13134312 , Image - 1

Unit-214, 214 Escarpment Crescent Collingwood, Simcoe, ON MLS® S13134312

Residential Condo & Other (Condo Townhouse)

$474900.0

Price drop by 13.6%

4 Beds
2 Baths
1400-1599 sq-ft

YOUR TURNKEY FOUR-SEASON RETREAT IN COLLINGWOOD. Welcome to the Cranberry Resort & Golf Court neighborhood, where comfort, lifestyle, and year-round a

40 Photos

5 Dawson Drive, Simcoe, ON , MLS #S14031914 , Image - 1

Unit-305, 5 Dawson Drive Collingwood, Simcoe, ON MLS® S14031914

Residential Condo & Other (Condo Townhouse)

$435000.0

2 Beds
1 Baths
700-799 sq-ft

Beautifully renovated from top to bottom, this 2-bed, 1-bath end-unit townhouse condo offers a true turnkey opportunity. The bright, open-concept uppe

50 Photos

172 Eighth Street, Simcoe, ON , MLS #S13880490 , Image - 1

Unit-505, 172 Eighth Street Collingwood, Simcoe, ON MLS® S13880490

Residential Condo & Other (Condo Apartment)

$334900.0

Price drop by 1.5%

2 Beds
1 Baths
1000-1199 sq-ft

There is still time to get in and settled before winter UNDERGROUND PARKING FOR UNDER $350K! You will not find a cheaper unit in Collingwood with un

8 Photos

17 Spooner Crescent S, Simcoe, ON , MLS #S14167036 , Image - 1

Unit-107, 17 Spooner Crescent S Collingwood, Simcoe, ON MLS® S14167036

Residential Condo & Other (Condo Apartment)

$444900.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to The View on Spooner Crescent, a modern and well-appointed ground-floor condo offering 2 bedrooms, and 2 bathrooms in the desirable Blue Fai

19 Photos

172 Eighth Street, Simcoe, ON , MLS #S12828326 , Image - 1

Unit-409, 172 Eighth Street Collingwood, Simcoe, ON MLS® S12828326

Residential Condo & Other (Condo Apartment)

$384900.0

Price drop by 8.1%

2 Beds
1 Baths
1000-1199 sq-ft

Welcome to The Galleries! This bright, spacious and freshly painted fourth floor 2-bedroom, 1-bathroom condo located in a sought after building which

Open House : Sat Nov 14, 10:00 AM to 12:00 PM

36 Photos

5 Dawson Drive, Simcoe, ON , MLS #S14116898 , Image - 1

Unit-327, 5 Dawson Drive Collingwood, Simcoe, ON MLS® S14116898

Residential Condo & Other (Condo Townhouse)

$370000.0

2 Beds
1 Baths
800-899 sq-ft

Outstanding 2-Bed Collingwood Townhome Near Georgian Bay! Filled with natural light, this upgraded 2-level condo features an open-concept upper floor

Open House : Sat Nov 14, 10:00 AM to 12:00 PM

23 Photos

15 Watts Crescent, Simcoe, ON , MLS #S14164084 , Image - 1

Unit-3, 15 Watts Crescent Collingwood, Simcoe, ON MLS® S14164084

Residential Condo & Other (Condo Townhouse)

$399900.0

3 Beds
2 Baths
1000-1199 sq-ft

3 bedroom condo in a quiet residential neighbourhood in Collingwood. Spacious entry with closet, a well-designed kitchen with new appliances and sink

16 Photos

17 Harbour Street W, Simcoe, ON , MLS #S12873986 , Image - 1

Unit-227, 17 Harbour Street W Collingwood, Simcoe, ON MLS® S12873986

Residential Condo & Other (Condo Townhouse)

$325000.0

Price drop by 26.1%

2 Beds
1 Baths
800-899 sq-ft

Welcome to Cranberry living in the heart of Collingwood! This private 2-bedroom, 1-bathroom condo offers a bright, stylish retreat in a sought-after c

47 Photos

24 Ramblings Way

Unit-502, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S13807064

Residential Condo & Other (Condo Apartment)

$394999.0

1 Beds
2 Baths
1000-1199 sq-ft

An exceptional opportunity to enjoy the Georgian Bay lifestyle at an incredible price! Offered at just $394,999, this spacious condo at Rupert's Landi

10 Photos

310 Maple Street, Simcoe, ON , MLS #S13518402 , Image - 1

310 Maple Street Collingwood, Simcoe, ON MLS® S13518402

Residential Freehold (Detached)

$449000.0

2 Beds
2 Baths
1100-1500 sq-ft

Walk to Downtown Collingwood! Endless potential awaits on this premium 28.8' x 165' deep lot, located steps from downtown Collingwood's shops, cafes,

25 Photos

515 MAPLE Street, Simcoe, ON , MLS #S13722988 , Image - 1

515 MAPLE Street Collingwood, Simcoe, ON MLS® S13722988

Residential Freehold (Detached)

$399000.0

Price drop by 16.7%

2 Beds
1 Baths
700-1100 sq-ft

Charming, affordable and well located in Collingwood. Tucked away on one of Collingwood's lovely tree streets, this adorable brick bungalow is a wonde

35 Photos

215 Pine Street, Simcoe, ON , MLS #S14131254 , Image - 1

Unit-5, 215 Pine Street Collingwood, Simcoe, ON MLS® S14131254

Residential Condo & Other (Condo Apartment)

$479000.0

2 Beds
2 Baths
1200-1399 sq-ft

DOWNTOWN CHARM. EXCEPTIONAL LIGHT AND SPACE. PRIME LOCATION AMID CENTURY HOMES ON ONE OF COLLINGWOOD'S DESIRABLE TREE STREETS. Cathedral ceilings, str

36 Photos

19 Dawson Drive, Simcoe, ON , MLS #S13756960 , Image - 1

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

21 Photos

34 Dawson Drive, Simcoe, ON , MLS #S14094792 , Image - 1

Unit-839, 34 Dawson Drive Collingwood, Simcoe, ON MLS® S14094792

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

5 Photos

31 Huron Street, Simcoe, ON , MLS #S14080222 , Image - 1

Unit-413, 31 Huron Street Collingwood, Simcoe, ON MLS® S14080222

Residential Condo & Other (Condo Apartment)

$465000.0

1 +1 Beds
1 Baths
700-799 sq-ft

Top 5 Reasons You Will Love This Condo: 1) Stunning new condo in the heart of Collingwood, perfectly situated near Nottawasaga Bay and offering an exc

15 Photos

9746 Beachwood Road, Simcoe, ON , MLS #S13823082 , Image - 1

9746 Beachwood Road Collingwood, Simcoe, ON MLS® S13823082

Residential Freehold (Vacant Land)

$194000.0

BUILD YOUR DREAM HOME OR EXPLORE AN EXCITING INVESTMENT OPPORTUNITY! This exceptional vacant lot offers incredible potential for a custom detached hom

48 Photos

17 Spooner Crescent, Simcoe, ON , MLS #S13834000 , Image - 1

Unit-206, 17 Spooner Crescent Collingwood, Simcoe, ON MLS® S13834000

Residential Condo & Other (Condo Apartment)

$389900.0

Price drop by 5.8%

2 Beds
2 Baths
800-899 sq-ft

Exceptional value in Collingwood isn't just about price-it's about how much lifestyle, space and convenience you get for it. Built in 2023, Unit 206 o

16 Photos

107 EIGHTH Street, Simcoe, ON , MLS #S13646606 , Image - 1

107 EIGHTH Street Collingwood, Simcoe, ON MLS® S13646606

Residential Freehold (Vacant Land)

$299900.0

Nestled on a generous 40 ft x 165 ft in-town lot, this property presents an exceptional opportunity for builders, investors, and those dreaming of a c

24 Photos

49 Raglan Street, Simcoe, ON , MLS #S13824352 , Image - 1

Unit-106, 49 Raglan Street Collingwood, Simcoe, ON MLS® S13824352

Residential Condo & Other (Condo Apartment)

$349000.0

2 Beds
1 Baths
800-899 sq-ft

Here is a wonderful opportunity to enjoy an affordable, carefree lifestyle in Sunset Suites! This popular 60+ senior living community operates under a

34 Photos

435 Walnut Street, Simcoe, ON , MLS #S13631308 , Image - 1

Unit-206, 435 Walnut Street Collingwood, Simcoe, ON MLS® S13631308

Residential Condo & Other (Condo Apartment)

$359900.0

1 Beds
1 Baths
800-899 sq-ft

Welcome to Walnut Woods-this spacious and beautifully maintained 1-bedroom, 1-bathroom condo is perfectly situated in the heart of Collingwood. With a

50 Photos

116 SPRUCE Street, Simcoe, ON , MLS #S14123304 , Image - 1

116 SPRUCE Street Collingwood, Simcoe, ON MLS® S14123304

Residential Freehold (Detached)

$475000.0

3 Beds
1 Baths
1500-2000 sq-ft

Developers, Investors, or First Time Home Buyers! Central Collingwood, 3 bedrooms, updated bathroom, large kitchen with island, main floor laundry, f

31 Photos

440 Oxbow Crescent W, Simcoe, ON , MLS #S13516864 , Image - 1

440 Oxbow Crescent W Collingwood, Simcoe, ON MLS® S13516864

Residential Condo & Other (Condo Townhouse)

$450000.0

3 +0 Beds
2 Baths
1400-1599 sq-ft

FULLY FURNISHED & BONUS: SELLER WILL PAY 3 MONTHS OF CONDO FEES*** Move-in ready- 3 BEDROOM- 2 BATH Cranberry Village Condo. Minutes to Blue Mountain

21 Photos

9 Harbour Street E, Simcoe, ON , MLS #S13037230 , Image - 1

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

Residential Condo & Other (Timeshare)

$19000.0

Price 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

28 Photos

13 Harbour Street W, Simcoe, ON , MLS #S13838396 , Image - 1

Unit-253, 13 Harbour Street W Collingwood, Simcoe, ON MLS® S13838396

Residential Condo & Other (Condo Townhouse)

$319000.0

2 Beds
1 Baths
700-799 sq-ft

Welcome to 253-13 Harbour Street West. This 2 bed, 1 bath townhouse condo nestled among the mature trees of Cranberry offers a fantastic opportunity f

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