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Houses for Sale in Collingwood ON Under $500K

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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: September 27, 2026

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

23 Photos

19 Dawson Drive, Simcoe, ON , MLS #S13832334 , Image - 1

Unit-53, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S13832334

Residential Condo & Other (Condo Apartment)

$359900.0

2 Beds
2 Baths
600-699 sq-ft

Your Collingwood lifestyle starts here! Whether you're looking for a full-time home, weekend escape or an easy-care investment, this bright 2-bedroom,

44 Photos

530 Tenth Street, Simcoe, ON , MLS #S13772254 , Image - 1

530 Tenth Street Collingwood, Simcoe, ON MLS® S13772254

Residential Condo & Other (Condo Townhouse)

$369900.0

3 Beds
2 Baths
1000-1199 sq-ft

Welcome to easy living in Collingwood, where the updates are done, the yard is yours to enjoy, and low-maintenance living is actually easy. This beaut

30 Photos

435 Walnut Street, Simcoe, ON , MLS #S13827436 , Image - 1

Unit-101, 435 Walnut Street Collingwood, Simcoe, ON MLS® S13827436

Residential Condo & Other (Condo Apartment)

$379000.0

1 Beds
1 Baths
800-899 sq-ft

Welcome to the desirable WALNUT WOODS condominium community, a well-maintained 16-unit brick building perfectly located in the heart of Collingwood. T

20 Photos

13 Raglan Street, Simcoe, ON , MLS #S13829354 , Image - 1

Unit-27, 13 Raglan Street Collingwood, Simcoe, ON MLS® S13829354

Residential Condo & Other (Condo Townhouse)

$495000.0

2 Beds
2 Baths
1000-1199 sq-ft

One of Collingwood's most sought-after neighbourhoods, Sunset Point! This charming and affordable 2-bedroom, 1.5-bathroom condo offers comfortable, lo

50 Photos

172 Eighth Street, Simcoe, ON , MLS #S13518098 , Image - 1

Unit-505, 172 Eighth Street Collingwood, Simcoe, ON MLS® S13518098

Residential Condo & Other (Condo Apartment)

$339900.0

Price drop by 2.9%

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

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

15 Photos

194 Erie Street, Simcoe, ON , MLS #S13824958 , Image - 1

194 Erie Street Collingwood, Simcoe, ON MLS® S13824958

Residential Freehold (Detached)

$325000.0

1 Beds
1 Baths
700-1100 sq-ft

Attention INVESTORS, DEVELOPERS, BIG THINKERS! This property is a rare opportunity to redevelop, rehabilitate, or reimagine a fully serviced town lot

48 Photos

541 Tenth Street, Simcoe, ON , MLS #S13823556 , Image - 1

541 Tenth Street Collingwood, Simcoe, ON MLS® S13823556

Residential Condo & Other (Condo Townhouse)

$480000.0

3 Beds
3 Baths
1200-1399 sq-ft

Beautifully updated end unit available for sale in Collingwood's desirable, family-friendly community of Vista Blue. This stunning home is situated i

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

9746 Beachwood Road Collingwood, Simcoe, ON MLS® S13823082

Residential Freehold (Vacant Land)

$194000.0

This exceptional property comes fully prepared for construction with major approvals already in place, including an NVCA permit, zoning certificate, l

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

50 Photos

288 Mariners Way, Simcoe, ON , MLS #S13817204 , Image - 1

288 Mariners Way Collingwood, Simcoe, ON MLS® S13817204

Residential Condo & Other (Condo Townhouse)

$359000.0

1 Beds
1 Baths
500-599 sq-ft

Four-season living at Lighthouse Point! This beautifully updated ground-level, 1-bedroom condo offers a low-maintenance lifestyle in one of Collingwoo

1 Photos

9618 Beachwood Road Collingwood, Simcoe, ON MLS® S13693842

Residential Freehold (Vacant Land)

$499000.0

Price drop by 16.7%

< 700 sq-ft

This 2.25-acre property sits on the corner of Beachwood Rd and King St, just south of Poplar Sideroad. The lot offers excellent severance potential, m

42 Photos

156 ESCARPMENT Crescent, Simcoe, ON , MLS #S13810570 , Image - 1

156 ESCARPMENT Crescent Collingwood, Simcoe, ON MLS® S13810570

Residential Condo & Other (Condo Townhouse)

$475000.0

3 +0 Beds
2 Baths
1200-1399 sq-ft

Welcome to this beautifully updated 3-bedroom, 2-bathroom condo townhome in the desirable Living Stone Resort Community. Offering an ideal blend of co

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)

$389900.0

Price drop by 6.9%

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

48 Photos

49 Trott Boulevard, Simcoe, ON , MLS #S13808690 , Image - 1

Unit-179, 49 Trott Boulevard Collingwood, Simcoe, ON MLS® S13808690

Residential Condo & Other (Condo Apartment)

$429000.0

2 Beds
2 Baths
900-999 sq-ft

Welcome to Harbourside 1 in Collingwood. Main floor, corner/end unit, bungalow style condo townhouse, with exterior storage locker and walkout to pati

24 Photos

71 Gibbard Crescent, Simcoe, ON , MLS #S13588594 , Image - 1

71 Gibbard Crescent Collingwood, Simcoe, ON MLS® S13588594

Residential Freehold (Semi-Detached )

$499000.0

Price drop by 3.9%

3 Beds
1 Baths
700-1100 sq-ft

Bright and fresh -- ready for you and your family. This is a two storey semi-detached with three bedrooms on the upper level and living room, kitchen

28 Photos

9771 Beachwood Road, Simcoe, ON , MLS #S13684022 , Image - 1

9771 Beachwood Road Collingwood, Simcoe, ON MLS® S13684022

Residential Freehold (Detached)

$499900.0

Price drop by 5.7%

4 Beds
2 Baths
1500-2000 sq-ft

Welcome to 9771 Beachwood Rd - a rare opportunity combining four-season living, an impressive 60' x 250' mature-treed lot and exciting long-term poten

32 Photos

9775 Beachwood Road, Simcoe, ON , MLS #S13684034 , Image - 1

9775 Beachwood Road Collingwood, Simcoe, ON MLS® S13684034

Residential Freehold (Detached)

$469900.0

Price drop by 6.0%

5 Beds
2 Baths
700-1100 sq-ft

Welcome to 9775 Beachwood Rd - a rare opportunity combining four-season living, an impressive 60' x 250' mature-treed lot and exciting long-term poten

35 Photos

6 Brandy Lane Drive, Simcoe, ON , MLS #S13579566 , Image - 1

Unit-105, 6 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S13579566

Residential Condo & Other (Condo Apartment)

$399000.0

Price drop by 2.7%

1 Beds
2 Baths
600-699 sq-ft

Welcome to this beautiful main-floor condo offering the perfect blend of comfort, convenience, and the Georgian Bay lifestyle. Backing onto the Georgi

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

28 Photos

442 Oxbow Crescent, Simcoe, ON , MLS #S13809084 , Image - 1

442 Oxbow Crescent Collingwood, Simcoe, ON MLS® S13809084

Residential Condo & Other (Condo Townhouse)

$319900.0

1 +1 Beds
2 Baths
600-699 sq-ft

Welcome to 442 Oxbow Crescent, a charming end-unit retreat in Collingwood's desirable Cranberry Resort and Golf Course neighbourhood. Furnished and mo

5 Photos

31 Huron Street, Simcoe, ON , MLS #S13706820 , Image - 1

Unit-413, 31 Huron Street Collingwood, Simcoe, ON MLS® S13706820

Residential Condo & Other (Condo Apartment)

$479000.0

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

21 Photos

9 Harbour Street E, Simcoe, ON , MLS #S12562086 , Image - 1

Unit-4119, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12562086

Residential Condo & Other (Timeshare)

$19000.0

Price drop by 67.2%

1 Beds
1 Baths
900-999 sq-ft

Exclusive Waterfront Ownership - Living Water Resort & Spa, Collingwood. Three Premium Weeks of Luxury, Lifestyle & Flexibility2026 is prepaid already

50 Photos

5 SPOONER Crescent, Simcoe, ON , MLS #S13110758 , Image - 1

Unit-314, 5 SPOONER Crescent Collingwood, Simcoe, ON MLS® S13110758

Residential Condo & Other (Condo Apartment)

$399000.0

Price drop by 11.1%

2 Beds
2 Baths
800-899 sq-ft

Beautifully maintained newly-built two-bedroom two-bath condo overlooking the Cranberry Golf Course, featuring a bright open-concept layout in a prime

31 Photos

9 Harbour Street, Simcoe, ON , MLS #S13794028 , Image - 1

Unit-6112/6114, 9 Harbour Street Collingwood, Simcoe, ON MLS® S13794028

Residential Condo & Other (Condo Apartment)

$21000.0

2 Beds
2 Baths
1200-1399 sq-ft

Discover Fractional Ownership At Living Waters Resort With This Turnkey 1/17th Share, Offering Three Annual Vacation Weeks Including Weeks 11, 12, And

23 Photos

590 Tenth Street, Simcoe, ON , MLS #S13736530 , Image - 1

590 Tenth Street Collingwood, Simcoe, ON MLS® S13736530

Residential Condo & Other (Condo Townhouse)

$340000.0

3 Beds
2 Baths
1000-1199 sq-ft

Townhouse style condo with it's own yard in the heart of Collingwood. An open concept main floor living area awaits with ceramic and laminate flooring

23 Photos

22 Dawson Drive, Simcoe, ON , MLS #S13433426 , Image - 1

Unit-530, 22 Dawson Drive Collingwood, Simcoe, ON MLS® S13433426

Residential Condo & Other (Condo Townhouse)

$475000.0

3 Beds
2 Baths
1200-1399 sq-ft

Discover the perfect blend of comfort, privacy, and convenience in this beautifully maintained 3-bedroom, 2-bathroom home nestled in the sought-after

37 Photos

711 Johnston Park Avenue, Simcoe, ON , MLS #S13741048 , Image - 1

711 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13741048

Residential Condo & Other (Condo Townhouse)

$459900.0

Price drop by 2.1%

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 privatebeach, b

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

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