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Houses for Sale in Collingwood ON Under $5 Million

Showing results 1 - 30 of 172

Are you looking for houses under $5m 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 $5m 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 $5m, including freehold homes, condos, and commercial properties.

Last Updated: December 05, 2025

39 Photos

2 EVERGREEN Road, Simcoe, ON , MLS #S12089114 , Image - 1

2 EVERGREEN Road Collingwood, Simcoe, ON MLS® S12089114

Residential Freehold (Detached)

$1599000.0

Price drop by 8.6%

4 +0 Beds
3 Baths
2500-3000 sq-ft

Imagine living just two minutes from Blue Mountain's ski hills, golf courses, shops, restaurants, and everything Collingwood has to offer. Hop on your

40 Photos

393 Second Street, Simcoe, ON , MLS #S12392067 , Image - 1

393 Second Street Collingwood, Simcoe, ON MLS® S12392067

Residential Freehold (Detached)

$999000.0

6 +0 Beds
3 Baths
2000-2500 sq-ft

TRIPLEX~ Great Opportunity for Investors~ ANNUAL RENTAL INCOME~$61 800/ yr, $5150 per month AND Tenants pay all utilities as well as snow removal! Thi

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

37 Photos

26 Davis Street, Simcoe, ON , MLS #S12404182 , Image - 1

26 Davis Street Collingwood, Simcoe, ON MLS® S12404182

Residential Freehold (Detached)

$879900.0

Price drop by 2.1%

3 +1 Beds
3 Baths
1100-1500 sq-ft

Discover this stunning 2,200 sq ft home nestled in the highly sought-after Creekside neighbourhood. Expertly renovated by Collingwood's acclaimed Kofo

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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48 Portland Street, Simcoe, ON , MLS #S12550258 , Image - 1

48 Portland Street Collingwood, Simcoe, ON MLS® S12550258

Residential Freehold (Att/Row/Townhouse)

$629900.0

3 Beds
4 Baths
1100-1500 sq-ft

Welcome to this 5-year young 2 storey townhome in beautiful Collingwood! The welcoming covered front porch is the perfect place to enjoy a beverage wh

40 Photos

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

42 Photos

16 Raglan Street, Simcoe, ON , MLS #S12580956 , Image - 1

Unit-404, 16 Raglan Street Collingwood, Simcoe, ON MLS® S12580956

Residential Condo & Other (Condo Apartment)

$599900.0

2 Beds
2 Baths
1200-1399 sq-ft

Welcome to Sunset Cove- where lifestyle meets location! This beautifully updated 2 bedroom, 2 bathroom condo offers relaxed low maintenance living jus

29 Photos

4 BUCKINGHAM Boulevard, Simcoe, ON , MLS #S12211234 , Image - 1

4 BUCKINGHAM Boulevard Collingwood, Simcoe, ON MLS® S12211234

Residential Freehold (Detached)

$2999990.0

Price drop by 1.6%

7 Beds
4 Baths
5000 + sq-ft

Experience unparalleled luxury and exceptional investment potential at 4 Buckingham Boulevard, an expansive estate offering over 5,000 sq. ft. of exqu

50 Photos

439 Birch Street, Simcoe, ON , MLS #S12277305 , Image - 1

439 Birch Street Collingwood, Simcoe, ON MLS® S12277305

Residential Freehold (Detached)

$1499999.0

4 Beds
3 Baths
2000-2500 sq-ft

Charming Brick Home on Coveted Tree street in Downtown Collingwood! Located on a desirable corner lot, this gem features a rare in-law suite complete

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

44 Photos

10 Water Street, Simcoe, ON , MLS #S12396594 , Image - 1

10 Water Street Collingwood, Simcoe, ON MLS® S12396594

Residential Freehold (Detached)

$824000.0

3 +2 Beds
2 Baths
1500-2000 sq-ft

In the Heart of Ontario's Four-Season Playground, tucked away next to the waterfront, this hidden enclave of homes is one of Collingwood's best-kept s

32 Photos

1 Hume Street, Simcoe, ON , MLS #S12451351 , Image - 1

Unit-422, 1 Hume Street Collingwood, Simcoe, ON MLS® S12451351

Residential Condo & Other (Condo Apartment)

$588888.0

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

Welcome to the bright east facing 4th floor, Edward suite, a 1 bedroom pls den with 10ft ceilings, upgraded 8ft interior doors, an open concept layout

50 Photos

849-851 Suncrest Circle, Simcoe, ON , MLS #S12151737 , Image - 1

849-851 Suncrest Circle Collingwood, Simcoe, ON MLS® S12151737

Residential Condo & Other (Condo Townhouse)

$1699000.0

Price drop by 10.3%

5 Beds
6 Baths
2750-2999 sq-ft

Welcome to a once-in-a-lifetime opportunity to own one of the largest condominiums in Collingwood's sought-after Lighthouse Point. This exceptional 2-

36 Photos

22 Hughes Street, Simcoe, ON , MLS #S12552626 , Image - 1

22 Hughes Street Collingwood, Simcoe, ON MLS® S12552626

Residential Freehold (Detached)

$899900.0

2 +2 Beds
3 Baths
1100-1500 sq-ft

Welcome to Pretty River Estates, a move-in ready Detached Home tucked away in a Peaceful Neighborhood Convenient to Everything Collingwood has to Offe

34 Photos

163 Collins Street, Simcoe, ON , MLS #S12451781 , Image - 1

163 Collins Street Collingwood, Simcoe, ON MLS® S12451781

Residential Freehold (Detached)

$600000.0

Price drop by 5.5%

3 Beds
3 Baths
700-1100 sq-ft

Your new home awaits in this highly desirable family friendly neighbourhood! Ideally located in this vibrant community with incredible schools, Admira

50 Photos

13 Belcher Street, Simcoe, ON , MLS #S12558282 , Image - 1

13 Belcher Street Collingwood, Simcoe, ON MLS® S12558282

Residential Freehold (Detached)

$699900.0

3 Beds
2 Baths
1500-2000 sq-ft

Welcome to 13 Belcher Street, your private Georgian Bay escape. Set on an expansive 100' x 170' treed lot, this beautifully updated 3-bedroom multi le

50 Photos

75 Indian Trail, Simcoe, ON , MLS #S12533084 , Image - 1

75 Indian Trail Collingwood, Simcoe, ON MLS® S12533084

Residential Freehold (Detached)

$2300000.0

6 Beds
4 Baths
3500-5000 sq-ft

This dream waterfront estate home could be yours for the 2025/2026 Ski season. Spanning nearly 5,000 square feet of living space, this six-bedroom hom

34 Photos

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

48 Photos

56 Georgian Manor Drive, Simcoe, ON , MLS #S12430539 , Image - 1

56 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S12430539

Residential Freehold (Detached)

$749000.0

Price drop by 9.2%

5 Beds
2 Baths
1500-2000 sq-ft

Welcome to 56 Georgian Manor Drive in beautiful Collingwood an incredible investment opportunity just minutes from Georgian Bay, downtown Collingwood

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

48 Photos

33 Foley Crescent, Simcoe, ON , MLS #S12439446 , Image - 1

33 Foley Crescent Collingwood, Simcoe, ON MLS® S12439446

Residential Freehold (Att/Row/Townhouse)

$699000.0

Price drop by 2.8%

3 Beds
3 Baths
1100-1500 sq-ft

Located in highly sought after family neighbourhood of Summit View, this bright corner Vista model townhome shows to perfection. 3 Bdrm., 2.5 bath and

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

50 Photos

13 Collship Lane, Simcoe, ON , MLS #S12423777 , Image - 1

13 Collship Lane Collingwood, Simcoe, ON MLS® S12423777

Residential Condo & Other (Condo Townhouse)

$1493000.0

3 Beds
4 Baths
2500-2749 sq-ft

For Sale: 13 Collship Lane, The Shipyards, Collingwood! 3 Beds | 4 Baths | 4 private secured Underground Parking | Private Elevator. Welcome to luxur

30 Photos

59 Cranberry Surf N/A, Simcoe, ON , MLS #S12473466 , Image - 1

59 Cranberry Surf N/A Collingwood, Simcoe, ON MLS® S12473466

Residential Condo & Other (Condo Townhouse)

$793000.0

3 Beds
2 Baths
1400-1599 sq-ft

Every day feels like a vacation in this exceptional three-storey waterfront townhome. Whether you're seeking a weekend escape, a seasonal retreat, or

32 Photos

7 Meadowlark Way, Simcoe, ON , MLS #S12434407 , Image - 1

7 Meadowlark Way Collingwood, Simcoe, ON MLS® S12434407

Residential Freehold (Detached)

$3590000.0

3 +2 Beds
4 Baths
2500-3000 sq-ft

MODERN, ORGANIC & TIMELESS CUSTOM-BUILT BUNGALOW FEATURING OVER 5,500 SQFT OF COMFORT-DRIVEN LIVING SPACE! Located in the equally coveted and conveni

18 Photos

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