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Houses for Sale in Collingwood ON Under $500K

Showing results 1 - 30 of 93

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: August 12, 2026

33 Photos

442 Hume Street, Simcoe, ON , MLS #S13654402 , Image - 1

442 Hume Street Collingwood, Simcoe, ON MLS® S13654402

Residential Freehold (Detached)

$485000.0

1 Beds
1 Baths
1100-1500 sq-ft

Welcome to 442 Hume Street in Collingwood, a charming 1-bedroom, 1-bathroom detached home situated on a large in-town lot with plenty of potential. T

23 Photos

55 Trott Boulevard, Simcoe, ON , MLS #S13665944 , Image - 1

Unit-139, 55 Trott Boulevard Collingwood, Simcoe, ON MLS® S13665944

Residential Condo & Other (Condo Townhouse)

$495000.0

3 Beds
2 Baths
1000-1199 sq-ft

Welcome to Unit 139 at 55 Trott Boulevard, a beautifully maintained main-floor condo offering comfortable, low-maintenance living in a sought-after lo

28 Photos

22 Dawson Drive, Simcoe, ON , MLS #S13133418 , Image - 1

Unit-538, 22 Dawson Drive Collingwood, Simcoe, ON MLS® S13133418

Residential Condo & Other (Condo Townhouse)

$320000.0

Price drop by 4.5%

1 Beds
2 Baths
600-699 sq-ft

Tucked away in a private corner of Cranberry Resort, this bright and inviting bungalow is ready for your personal touch. The open-concept layout seaml

42 Photos

184 Eighth Street, Simcoe, ON , MLS #S13649502 , Image - 1

Unit-203, 184 Eighth Street Collingwood, Simcoe, ON MLS® S13649502

Residential Condo & Other (Condo Apartment)

$330000.0

2 Beds
1 Baths
800-899 sq-ft

Experience the best of four-season living in this bright and spacious 2-bedroom, 1-bathroom condo, ideally located in the heart of Collingwood. Whethe

14 Photos

23 Dawson Drive, Simcoe, ON , MLS #S13661838 , Image - 1

Unit-93, 23 Dawson Drive Collingwood, Simcoe, ON MLS® S13661838

Residential Condo & Other (Condo Townhouse)

$449900.0

2 Beds
2 Baths
600-699 sq-ft

Pride of ownership can be seen in this 2 bedroom/2 bathroom condo at Cranberry/Living Stone. Open concept unit features newer flooring and a large so

36 Photos

9 Harbour Street E, Simcoe, ON , MLS #S13576138 , Image - 1

Unit-3112/14, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S13576138

Residential Condo & Other (Condo Apartment)

$10000.0

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

Welcome to Living Waters Resort, where luxury living meets shared ownership amidst unparalleled amenities. With our fractional 1/17th ownership opport

23 Photos

590 Tenth Street, Simcoe, ON , MLS #S13070170 , Image - 1

590 Tenth Street Collingwood, Simcoe, ON MLS® S13070170

Residential Condo & Other (Condo Townhouse)

$350000.0

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

33 Photos

5 Winters Crescent NW, Simcoe, ON , MLS #S13647122 , Image - 1

5 Winters Crescent NW Collingwood, Simcoe, ON MLS® S13647122

Residential Condo & Other (Condo Townhouse)

$479900.0

3 Beds
2 Baths
1400-1599 sq-ft

Nestled into a cozy CRESCENT of MODERN TOWNES this BIRCH INTERIOR UNIT aims to please. With a soaring exterior, lots of windows complimented by BRICK

35 Photos

536 Tenth Street, Simcoe, ON , MLS #S13602674 , Image - 1

536 Tenth Street Collingwood, Simcoe, ON MLS® S13602674

Residential Condo & Other (Condo Townhouse)

$349900.0

3 Beds
2 Baths
900-999 sq-ft

FREE CONDO FEES FOR A YEAR. Beautifully renovated and move-in ready, this fully finished condo townhouse offers stylish, low-maintenance living in one

15 Photos

19 Dawson Drive, Simcoe, ON , MLS #S13658428 , Image - 1

Unit-57, 19 Dawson Drive Collingwood, Simcoe, ON MLS® S13658428

Residential Condo & Other (Condo Apartment)

$449990.0

2 Beds
2 Baths
700-799 sq-ft

BRIGHT UPPER UNIT IN GLEN II CRANBERRY VILLAGE. CARPET FREE! OPEN CONCEPT, SUN FILLED UNIT, 2 BED, 2 BATH. WOOD FIREPLACE, UPGRADED BREAKFAST BAR. LAR

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

42 Photos

156 ESCARPMENT Crescent, Simcoe, ON , MLS #S13654698 , Image - 1

156 ESCARPMENT Crescent Collingwood, Simcoe, ON MLS® S13654698

Residential Condo & Other (Condo Townhouse)

$485000.0

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 (formerly Cranberry Resort). O

24 Photos

9 Trafalgar Road, Simcoe, ON , MLS #S13442564 , Image - 1

9 Trafalgar Road Collingwood, Simcoe, ON MLS® S13442564

Residential Condo & Other (Condo Townhouse)

$410000.0

Price drop by 8.9%

3 Beds
3 Baths
1400-1599 sq-ft

Nestled against a peaceful forest backdrop, this beautifully updated 3-bedroom, 3-bathroom condo townhome in Whisper Woods offers refined living in th

15 Photos

9 Harbour Street E, Simcoe, ON , MLS #S13611308 , Image - 1

Unit-6412/14, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S13611308

Residential Condo & Other (Condo Apartment)

$34900.0

2 Beds
2 Baths
1200-1399 sq-ft

Top-Floor Waterfront Living in Collingwood with all maintenance fees paid until 2028! Pack your bags and unwind at Living Water Resort & Spa, a premie

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)

$394900.0

Price drop by 5.8%

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

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

28 Photos

4 Kimberly Lane

Unit-404, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® S13620612

Residential Condo & Other (Condo Apartment)

$425000.0

1 Beds
1 Baths
700-799 sq-ft

Welcome to effortless four-season living at The Marquis at Royal Windsor-a beautifully designed 700 sq. ft. one-bedroom suite that combines comfort, c

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

5 Photos

31 Huron Street, Simcoe, ON , MLS #S13571706 , Image - 1

Unit-413, 31 Huron Street Collingwood, Simcoe, ON MLS® S13571706

Residential Condo & Other (Condo Apartment)

$489900.0

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

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

38 Photos

51 Trott Boulevard, Simcoe, ON , MLS #S13568386 , Image - 1

Unit-171, 51 Trott Boulevard Collingwood, Simcoe, ON MLS® S13568386

Residential Condo & Other (Condo Townhouse)

$454000.0

2 Beds
2 Baths
1000-1199 sq-ft

Sought after ranch style bungalow end unit townhouse. Flat entrance through the front door into this sun-filled open concept home. Tastefully updated

39 Photos

55 Trott Boulevard, Simcoe, ON , MLS #S13138386 , Image - 1

Unit-114, 55 Trott Boulevard Collingwood, Simcoe, ON MLS® S13138386

Residential Condo & Other (Condo Townhouse)

$424900.0

Price drop by 3.2%

2 Beds
2 Baths
1000-1199 sq-ft

New Price!! Welcome to this bright and inviting 2-bedroom, 2-bathroom condo in the heart of Collingwood. Featuring contemporary styling and ideally

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

24 Photos

9 Harbour Street, Simcoe, ON , MLS #S12483435 , Image - 1

Unit-5117-5119, 9 Harbour Street Collingwood, Simcoe, ON MLS® S12483435

Residential Condo & Other (Timeshare)

$35000.0

Price drop by 41.7%

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

3 WEEK FRACTIONAL OWNERSHIP AT Collingwood's only waterfront resort. Available weeks are #39, #40& #50 (4th week of September, 1st week of October and

40 Photos

5 Dawson Drive, Simcoe, ON , MLS #S13626190 , Image - 1

Unit-305, 5 Dawson Drive Collingwood, Simcoe, ON MLS® S13626190

Residential Condo & Other (Condo Townhouse)

$449900.0

2 Beds
1 Baths
700-799 sq-ft

Beautifully renovated from top to bottom, this 2-bedroom, 1-bathroom end-unit townhouse condo is tucked among the mature trees of Cranberry and offers

37 Photos

711 Johnston Park Avenue, Simcoe, ON , MLS #S13621192 , Image - 1

711 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13621192

Residential Condo & Other (Condo Townhouse)

$479900.0

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,

49 Photos

23 Dawson Drive, Simcoe, ON , MLS #S13138956 , Image - 1

Unit-98, 23 Dawson Drive Collingwood, Simcoe, ON MLS® S13138956

Residential Condo & Other (Condo Apartment)

$399000.0

Price drop by 11.1%

2 Beds
2 Baths
700-799 sq-ft

Welcome to this Lovely Ground Floor Condo tucked away in Secluded Setting along 23 Dawson Drive, Unit # 98. The Private Patio is set up perfectly for

43 Photos

9 Harbour Street E, Simcoe, ON , MLS #S13077362 , Image - 1

Unit-6411/6413, 9 Harbour Street E Collingwood, Simcoe, ON MLS® S13077362

Residential Condo & Other (Condo Apartment)

$48500.0

Price drop by 19.2%

2 Beds
2 Baths
1200-1399 sq-ft

Welcome to Living Water Resort & Spa, your four-season getaway on the shores of Georgian Bay in beautiful Collingwood. This fractional ownership oppor

35 Photos

10 Brandy Lane Drive, Simcoe, ON , MLS #S13612040 , Image - 1

Unit-204, 10 Brandy Lane Drive Collingwood, Simcoe, ON MLS® S13612040

Residential Condo & Other (Condo Apartment)

$424000.0

1 Beds
2 Baths
700-799 sq-ft

One of the most private locations in the Wyldewood Community, backing on to green space and the trails. Comfortable Year round living or your four sea

23 Photos

184 Eighth Street, Simcoe, ON , MLS #S13609596 , Image - 1

Unit-307, 184 Eighth Street Collingwood, Simcoe, ON MLS® S13609596

Residential Condo & Other (Condo Apartment)

$299900.0

2 Beds
1 Baths
800-899 sq-ft

Here's a unique chance to own a condo in the sought-after West Winds building! Properties here rarely become available. This secure, centrally located

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