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Houses for Sale in Collingwood ON Under $500K

Showing results 1 - 30 of 42

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: December 05, 2025

46 Photos

14 Dawson Drive, Simcoe, ON , MLS #S12185645 , Image - 1

Unit-415, 14 Dawson Drive Collingwood, Simcoe, ON MLS® S12185645

Residential Condo & Other (Condo Townhouse)

$485000.0

Price drop by 8.3%

2 Beds
2 Baths
900-999 sq-ft

Beautifully Updated Townhome in Prime Collingwood Location.Tucked away among the trees for added privacy, this updated two-story townhome offers the p

50 Photos

13 Harbour Street W, Simcoe, ON , MLS #S12584390 , Image - 1

Unit-256, 13 Harbour Street W Collingwood, Simcoe, ON MLS® S12584390

Residential Condo & Other (Condo Apartment)

$497000.0

2 Beds
2 Baths
1000-1199 sq-ft

Bungalow living with a modern, elevated feel! The updated 2-bedroom, 2-bathroom end-unit offers privacy, comfort, and thoughtful design throughout. Pe

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9 HARBOUR Street E, Simcoe, ON , MLS #S10899627 , Image - 1

Unit-6201-03, 9 HARBOUR Street E Collingwood, Simcoe, ON MLS® S10899627

Residential Condo & Other (Condo Apartment)

$70000.0

Price drop by 17.6%

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

Invest in an ownership share of Phase 2 of LIVING WATER RESORT AND SPA on the shores of Georgian Bay in the beautiful town of Collingwood. NOTE: this

30 Photos

17 Spooner Crescent, Simcoe, ON , MLS #S12574974 , Image - 1

Unit-102, 17 Spooner Crescent Collingwood, Simcoe, ON MLS® S12574974

Residential Condo & Other (Condo Apartment)

$445000.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to Spooner Crescent, a modern and well-appointed ground-floor condo offering 2 bedrooms, 2 bathrooms, and underground parking in the desirable

19 Photos

3 Brandy Lane Drive, Simcoe, ON , MLS #S12574958 , Image - 1

Unit-205, 3 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S12574958

Residential Condo & Other (Condo Apartment)

$464900.0

2 Beds
2 Baths
800-899 sq-ft

Welcome To Wyldewood! The Home Of Ski And Golf Enthusiasts. A Four - Season Community In The Heart Of Collingwood. Make This Two Bedroom, 2 Bath Your

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2 Anchorage Crescent, Simcoe, ON , MLS #S12516968 , Image - 1

Unit-200, 2 Anchorage Crescent Collingwood, Simcoe, ON MLS® S12516968

Residential Condo & Other (Condo Apartment)

$399000.0

1 Beds
1 Baths
500-599 sq-ft

Welcome to 2 Anchorage Crescent #200, this is a beautiful 1-bedroom, 1-bathroom corner unit that perfectly blends modern comfort with cozy charm. Enjo

29 Photos

19 Dawson Drive, Simcoe, ON , MLS #S12557918 , Image - 1

Unit-47, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S12557918

Residential Condo & Other (Condo Townhouse)

$287000.0

1 Beds
1 Baths
500-599 sq-ft

Best value in Collingwood! Affordable, turn-Key Livingstone Resort Condo! Well-maintained and move-in ready one-bedroom, one-bathroom condo in the sou

21 Photos

1 Chamberlain Crescent, Simcoe, ON , MLS #S12424501 , Image - 1

Unit-102, 1 Chamberlain Crescent Collingwood, Simcoe, ON MLS® S12424501

Residential Condo & Other (Condo Apartment)

$474900.0

Price drop by 5.0%

2 Beds
1 Baths
700-799 sq-ft

End Unit Ground Floor Condo Just Minutes from Blue Mountain Ski Resort Perfect for Winter Lovers! Spacious 2-bedroom, 1-bath end-unit condo. Ideally

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17 Spooner Crescent, Simcoe, ON , MLS #S12304375 , Image - 1

Unit-205, 17 Spooner Crescent Collingwood, Simcoe, ON MLS® S12304375

Residential Condo & Other (Condo Apartment)

$450000.0

Price drop by 4.2%

2 Beds
2 Baths
800-899 sq-ft

Condo Living At The Most Affordable Price in the Building! The Eagle model offers a bright, open-concept 2-bedroom, 2-bathroom condo with 9-foot ceili

14 Photos

155 Vacation Inn Drive, Simcoe, ON , MLS #S12214641 , Image - 1

155 Vacation Inn Drive Collingwood, Simcoe, ON MLS® S12214641

Residential Condo & Other (Timeshare)

$14500.0

Price drop by 19.4%

2 Beds
3 Baths
800-899 sq-ft

Spend the Holidays in Collingwood Every Year! Welcome to your home for the holidays at part of the sought-after Georgian Bay Hotel community in Colli

15 Photos

553 Tenth Street, Simcoe, ON , MLS #S12501448 , Image - 1

553 Tenth Street Collingwood, Simcoe, ON MLS® S12501448

Residential Condo & Other (Condo Townhouse)

$372500.0

Price drop by 1.3%

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

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

49 Photos

750 Johnston Park Avenue, Simcoe, ON , MLS #S12529944 , Image - 1

Unit-2006, 750 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S12529944

Residential Condo & Other (Condo Apartment)

$499000.0

2 Beds
2 Baths
1000-1199 sq-ft

Experience the vibrant lifestyle at Lighthouse Point Yacht & Tennis Club, a premier waterfront community spanning over 125 acres and offering a wealth

50 Photos

331 MARINERS Way, Simcoe, ON , MLS #S12520826 , Image - 1

331 MARINERS Way Collingwood, Simcoe, ON MLS® S12520826

Residential Condo & Other (Condo Apartment)

$499900.0

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

17 Dawson Drive, Simcoe, ON , MLS #S12503666 , Image - 1

Unit-29, 17 Dawson Drive Collingwood, Simcoe, ON MLS® S12503666

Residential Condo & Other (Condo Apartment)

$399000.0

2 Beds
2 Baths
700-799 sq-ft

Lovingly updated two-bedroom, two bathroom upper-level condo offers an easy option for anyone looking to enter the market, simplify their living space

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

21 Photos

9 Harbour Street E

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

Residential Condo & Other (Timeshare)

$60000.0

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

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479 Oxbow Crescent, Simcoe, ON , MLS #S12436635 , Image - 1

479 Oxbow Crescent Collingwood, Simcoe, ON MLS® S12436635

Residential Condo & Other (Condo Townhouse)

$465000.0

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 (f

23 Photos

215 Pine Street, Simcoe, ON , MLS #S12081876 , Image - 1

Unit-4, 215 Pine Street Collingwood, Simcoe, ON MLS® S12081876

Residential Condo & Other (Condo Apartment)

$439000.0

Price drop by 21.5%

2 Beds
2 Baths
1200-1399 sq-ft

Spacious 2 bedroom, 2 bathroom condominium located on a historic and very pretty street in Collingwood with century homes. Walking distance to many am

19 Photos

24 Ramblings Way

Unit-305, 24 Ramblings Way Collingwood, Simcoe, ON MLS® S12469689

Residential Condo & Other (Condo Apartment)

$429000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to Unit 305 in Bayview Tower at Ruperts Landing one of Collingwood's most desirable waterfront communities! This 2-bedroom, 2-bathroom condo o

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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

6 Photos

9742 Beachwood Road, Simcoe, ON , MLS #S12065510 , Image - 1

9742 Beachwood Road Collingwood, Simcoe, ON MLS® S12065510

Residential Freehold (Vacant Land)

$199000.0

< 700 sq-ft

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

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)

$78000.0

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

21 Photos

9 Harbour Street E, Simcoe, ON , MLS #S12222241 , Image - 1

Unit-2311/13, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S12222241

Residential Condo & Other (Condo Apartment)

$20000.0

Price drop by 33.3%

2 Beds
2 Baths
1200-1399 sq-ft

Escape to Luxury in Collingwood! Pack your bags and unwind at Living Water Resort & Spa, a premier waterfront destination nestled in the heart of Coll

8 Photos

27 Braeside Street, Simcoe, ON , MLS #S12424527 , Image - 1

27 Braeside Street Collingwood, Simcoe, ON MLS® S12424527

Residential Freehold (Vacant Land)

$249888.0

< 700 sq-ft

Top 5 Reasons You Will Love This Property: 1) Nestled in the desirable Beachwood community, you're just minutes from Collingwood, Wasaga Beach, and Bl

4 Photos

9736 Beachwood Road, Simcoe, ON , MLS #S12050384 , Image - 1

9736 Beachwood Road Collingwood, Simcoe, ON MLS® S12050384

Residential Freehold (Vacant Land)

$199000.0

< 700 sq-ft

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

19 Photos

9 Harbour Street E

Unit-3117-19, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S11990375

Residential Condo & Other (Condo Apartment)

$78600.0

2 Beds
2 Baths
1000-1199 sq-ft

Delight in summertime on Georgian Bay! With fully paid fees until 2027, this is your opportunity to invest in a vacation spot in Collingwood.Located o

20 Photos

22 Dawson Drive, Simcoe, ON , MLS #S12399284 , Image - 1

Unit-534, 22 Dawson Drive Collingwood, Simcoe, ON MLS® S12399284

Residential Condo & Other (Condo Townhouse)

$385000.0

2 Beds
2 Baths
800-899 sq-ft

Welcome to this bright and inviting 2-bedroom, 2-bathroom townhouse, designed with a unique reverse floor plan. The upper level is the heart of the ho

48 Photos

49 Trott Boulevard, Simcoe, ON , MLS #S12405724 , Image - 1

Unit-179, 49 Trott Boulevard Collingwood, Simcoe, ON MLS® S12405724

Residential Condo & Other (Condo Apartment)

$439000.0

2 Beds
2 Baths
900-999 sq-ft

Welcome to Harbourside 1 in Collingwood. Bungalow style condo townhouse, main floor corner, with storage locker and walkout to patio. 2 bedroom, 2 bat

38 Photos

288 Mariners Way, Simcoe, ON , MLS #40747330 , Image - 1

288 Mariners Way Collingwood, Simcoe, ON MLS® 40747330

Residential (Row/Townhouse)

$459000

1 Beds
1 Baths
613 sq-ft

Welcome to Lighthouse Point, one of the most sought-after exclusive waterfront condominium communities along the scenic shores of Georgian Bay. Offeri

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460 Ontario Street, Simcoe, ON , MLS #40712527 , Image - 1

Unit-406, 460 Ontario Street Collingwood, Simcoe, ON MLS® 40712527

Residential (Condo/Apartment Unit)

$350000

Price drop by 7.9%

2 Beds
1 Baths
840 sq-ft

Welcome To Bayview Terrace. Suite 406 At 460 Ontario Street Is A Spacious, Sun Filled Two-Bedroom Condo Offering An Unbeatable Combination Of Comfort

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