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Houses for Sale in Collingwood ON Under $500K

Showing results 1 - 21 of 21

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: June 28, 2026

9 Photos

11325 26 Highway, Simcoe, ON , MLS #S13495060 , Image - 1

11325 26 Highway Collingwood, Simcoe, ON MLS® S13495060

Residential Freehold (Vacant Land)

$300000.0

Developers take note. R-3 zoning allows a number of possibilities to build a multi-unit building. Close to skiing, bus route, golf, and hiking trails.

15 Photos

553 Tenth Street, Simcoe, ON , MLS #S13426260 , Image - 1

553 Tenth Street Collingwood, Simcoe, ON MLS® S13426260

Residential Condo & Other (Condo Townhouse)

$349900.0

3 +1 Beds
3 Baths
1200-1399 sq-ft

Attention first time home buyers and investors!! This 4-bedroom (3+1) townhouse condo is priced to sell. With a few cosmetic upgrades, you could trans

24 Photos

172 Escarpment Crescent, Simcoe, ON , MLS #S12994870 , Image - 1

172 Escarpment Crescent Collingwood, Simcoe, ON MLS® S12994870

Residential Condo & Other (Condo Townhouse)

$415000.0

Price drop by 2.4%

2 Beds
1 Baths
800-899 sq-ft

An extremely rare opportunity in Collingwood-featuring gas heating, an exceptional and seldom-found feature. Enhanced with custom ductwork to the main

46 Photos

14 Dawson Drive, Simcoe, ON , MLS #S13028014 , Image - 1

Unit-415, 14 Dawson Drive Collingwood, Simcoe, ON MLS® S13028014

Residential Condo & Other (Condo Townhouse)

$415000.0

Price drop by 5.7%

2 Beds
2 Baths
900-999 sq-ft

Beautifully updated townhome in a prime Collingwood location, tucked among the trees for added privacy and a true four-season feel. This two-storey ho

49 Photos

750 Johnston Park Avenue, Simcoe, ON , MLS #S13155910 , Image - 1

Unit-2006, 750 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13155910

Residential Condo & Other (Condo Apartment)

$489000.0

Price drop by 2.0%

2 Beds
2 Baths
1000-1199 sq-ft

Experience the best of four-season waterfront living at Lighthouse Point Yacht & Tennis Club, one of the area's most sought-after resort-style communi

19 Photos

3 Brandy Lane Drive, Simcoe, ON , MLS #S13473544 , Image - 1

Unit-205, 3 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S13473544

Residential Condo & Other (Condo Apartment)

$469000.0

2 Beds
2 Baths
700-799 sq-ft

Welcome to the Collingwood lifestyle in this 4 season turn-key 2-bedroom, 2-bathroom condo located in the highly desirable Wyldewood Trailside Communi

29 Photos

19 Dawson Drive, Simcoe, ON , MLS #S13436576 , Image - 1

Unit-47, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S13436576

Residential Condo & Other (Condo Townhouse)

$259900.0

1 Beds
1 Baths
0-499 sq-ft

Turn-key 1-bed, 1-bath condo in Livingstone Resort (formerly Cranberry), perfect for first-time buyers, retirees, or a four-season getaway. This well-

42 Photos

440 Oxbow Crescent, Simcoe, ON , MLS #S12936156 , Image - 1

440 Oxbow Crescent Collingwood, Simcoe, ON MLS® S12936156

Residential Condo & Other (Condo Townhouse)

$469000.0

3 Beds
2 Baths
1200-1399 sq-ft

Discover this bright, spacious 3-bedroom, 2-bath condo, perfectly located at Livingstone Resort (formerly Cranberry). The open-concept main floor feat

50 Photos

331 MARINERS Way, Simcoe, ON , MLS #S12931640 , Image - 1

331 MARINERS Way Collingwood, Simcoe, ON MLS® S12931640

Residential Condo & Other (Condo Apartment)

$464900.0

Price drop by 7.0%

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

30 Photos

35 Dawson Drive, Simcoe, ON , MLS #S13434106 , Image - 1

Unit-4, 35 Dawson Drive Collingwood, Simcoe, ON MLS® S13434106

Residential Condo & Other (Condo Townhouse)

$479900.0

3 Beds
2 Baths
1400-1599 sq-ft

COME & ENJOY THE WARMTH OF THE SUMMER WHERE THE MOUNTAINS MEET THE BAY & BRAND NEW HOMES ARE TAX FREE for EVERYONE. This MODERN INTERIOR BIRCH MODEL l

33 Photos

31 Huron Street, Simcoe, ON , MLS #S13427966 , Image - 1

Unit-412, 31 Huron Street Collingwood, Simcoe, ON MLS® S13427966

Residential Condo & Other (Condo Apartment)

$499900.0

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

Top 5 Reasons You Will Love This Condo: 1) Here's your opportunity to own one of the few remaining suites at Harbour House, Collingwood's sought-after

48 Photos

49 Trott Boulevard, Simcoe, ON , MLS #S13418516 , Image - 1

Unit-179, 49 Trott Boulevard Collingwood, Simcoe, ON MLS® S13418516

Residential Condo & Other (Condo Apartment)

$439000.0

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

6 Photos

9742 Beachwood Road, Simcoe, ON , MLS #S13232200 , Image - 1

9742 Beachwood Road Collingwood, Simcoe, ON MLS® S13232200

Residential Freehold (Vacant Land)

$179000.0

Residential building lot located minutes to beaches, shopping, trails, skiing and golf. Located on the north side of Beachwood Rd in the east end of C

4 Photos

9736 Beachwood Road, Simcoe, ON , MLS #S13232192 , Image - 1

9736 Beachwood Road Collingwood, Simcoe, ON MLS® S13232192

Residential Freehold (Vacant Land)

$179000.0

Residential building lot located minutes to beaches, shopping, trails, skiing and golf. Located on the north side of Beachwood Rd. in east end of Coll

29 Photos

9 Harbour Street E, Simcoe, ON , MLS #S12099425 , Image - 1

Unit-3109-3111, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12099425

Residential Condo & Other (Other)

$29000.0

Price drop by 62.8%

2 Beds
2 Baths
1200-1399 sq-ft

This 3 week G6 fractional ownership for weeks 31-33-46, with a spectacular view of Georgian Bay and historic Collingwood grain terminals could be your

3 Photos

41 Conc 10 Nottawasaga PT 21 N/A, Simcoe, ON , MLS #S9364458 , Image - 1

41 Conc 10 Nottawasaga PT 21 N/A Collingwood, Simcoe, ON MLS® S9364458

Residential Freehold (Vacant Land)

$499000.0

Price drop by 9.1%

Excellent opportunity for a builder or investor for future development. Residential building lot measuring 100 x 150 ft. lot in beautiful sought after

34 Photos

479 Oxbow Crescent, Simcoe, ON , MLS #S13069882 , Image - 1

479 Oxbow Crescent Collingwood, Simcoe, ON MLS® S13069882

Residential Condo & Other (Condo Townhouse)

$420000.0

2 Beds
2 Baths
1000-1199 sq-ft

The perfect home or getaway in Collingwood - Ontario's Four Season playground. This remarkable condo townhome is located in Living Stone Community (fo

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PT LT 2 PT 1 Downer Street, Simcoe, ON , MLS #S12835754 , Image - 1

PT LT 2 PT 1 Downer Street Collingwood, Simcoe, ON MLS® S12835754

Residential Freehold (Vacant Land)

$419000.0

< 700 sq-ft

Premium vacant building lot in a highly sought-after Collingwood location, just steps from the sparkling shores of Georgian Bay and minutes to downtow

21 Photos

9 Harbour Street E

Unit-4109-41, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S11931442

Residential Condo & Other (Timeshare)

$40000.0

Price drop by 33.3%

2 Beds
2 Baths
0-499 sq-ft

3 WEEK FRACTIONAL OWNERSHIP AT Collingwood's only waterfront resort. Located on the 4th floor of Living Water Resort, this unit offers amazing views o

23 Photos

9 HARBOUR Street E, Simcoe, ON , MLS #S10893954 , Image - 1

Unit-2116-2118, 9 HARBOUR Street E Collingwood, Simcoe, ON MLS® S10893954

Residential Condo & Other (Condo Apartment)

$48000.0

Price drop by 40.0%

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

REDUCED AGAIN!!! BRING ALL OFFERS!!! VERY MOTIVATED SELLER!!! 3 Week Fractional Ownership at Collingwood's only waterfront resort. With lock off

27 Photos

9 Harbour Street E, Simcoe, ON , MLS #S12478205 , Image - 1

Unit-5209, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12478205

Residential Condo & Other (Other)

$35000.0

2 Beds
2 Baths
1200-1399 sq-ft

Welcome to Living Water Resort & Spa! Your stunning Collingwood getaway. You could own a fraction of this unit, spend three amazing weeks at Living Wa

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