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Houses for Sale in Collingwood ON Under $5 Million

Showing results 1 - 30 of 166

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 17, 2025

5 Photos

169 Second Street, Simcoe, ON , MLS #S12226359 , Image - 1

169 Second Street Collingwood, Simcoe, ON MLS® S12226359

Residential Freehold (Detached)

$1950000.0

4 Beds
4 Baths
2000-2500 sq-ft

Welcome to Charming Collingwood Living. Where Luxury Meets Location! Discover the perfect blend of elegance, comfort, and convenience in this stunning

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

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

40 Photos

17 Gregory Avenue, Simcoe, ON , MLS #S12419007 , Image - 1

17 Gregory Avenue Collingwood, Simcoe, ON MLS® S12419007

Residential Freehold (Att/Row/Townhouse)

$789000.0

3 Beds
4 Baths
1100-1500 sq-ft

Luxury Living Awaits In The Highly Coveted Blue Fairway Community! The Pebble Beach End-Unit Shows 10+ & Boasts 6 Additional Windows For An Abundance

36 Photos

465 Mariners Way, Simcoe, ON , MLS #S12629484 , Image - 1

465 Mariners Way Collingwood, Simcoe, ON MLS® S12629484

Residential Condo & Other (Condo Apartment)

$575000.0

2 Beds
2 Baths
800-899 sq-ft

2 bed, 2 bath second floor unit in Lighthouse Point that includes a 30 ft Boat Slip and is steps away from the Rec Centre, is being sold partially fur

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

42 Photos

423 Mariners Way, Simcoe, ON , MLS #S12409482 , Image - 1

423 Mariners Way Collingwood, Simcoe, ON MLS® S12409482

Residential Condo & Other (Condo Townhouse)

$899000.0

Price drop by 5.4%

3 Beds
2 Baths
1200-1399 sq-ft

Welcome to Lighthouse Point! Discover this rarely available 3-bedroom Garden Home, ideally located near the clubhouse in one of the most sought-after

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

49 Photos

1 Hume Street, Simcoe, ON , MLS #S12412514 , Image - 1

Unit-PH609, 1 Hume Street Collingwood, Simcoe, ON MLS® S12412514

Residential Condo & Other (Condo Apartment)

$1285000.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to Monaco, a landmark of sophisticated living in Downtown Collingwood, where this spectacular Penthouse condo awaits. This truly special 2-bed

45 Photos

73 Findlay Drive, Simcoe, ON , MLS #S12467719 , Image - 1

73 Findlay Drive Collingwood, Simcoe, ON MLS® S12467719

Residential Freehold (Detached)

$999000.0

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

Welcome to this spacious and immaculate custom bungalow in a prime location backing onto greenbelt! Offering an open-concept floor plan that perfectly

45 Photos

234 Pine Street, Simcoe, ON , MLS #S12456481 , Image - 1

234 Pine Street Collingwood, Simcoe, ON MLS® S12456481

Residential Freehold (Detached)

$1899000.0

6 Beds
5 Baths
3000-3500 sq-ft

There is something rather enchanting about living a on a tree-lined street in a home with history that is located right in the heart of the downtown H

36 Photos

29 Archer Avenue, Simcoe, ON , MLS #S12156289 , Image - 1

29 Archer Avenue Collingwood, Simcoe, ON MLS® S12156289

Residential Freehold (Att/Row/Townhouse)

$629900.0

Price drop by 13.7%

3 Beds
3 Baths
1100-1500 sq-ft

NEW PRICE REDUCTION!!! Welcome to this beautiful, freehold townhome found in the very popular Summit View community in Collingwood. This 3 Bedroom, 2

27 Photos

365 Mariners Way, Simcoe, ON , MLS #S12546106 , Image - 1

365 Mariners Way Collingwood, Simcoe, ON MLS® S12546106

Residential Condo & Other (Common Element Condo)

$649000.0

3 Beds
2 Baths
1200-1399 sq-ft

Must See. This generous ground-floor 3-bedroom unit offers the rare combination of single-level living and plenty of space to grow into - the kind of

16 Photos

31 Huron Street, Simcoe, ON , MLS #S12432849 , Image - 1

Unit-609, 31 Huron Street Collingwood, Simcoe, ON MLS® S12432849

Residential Condo & Other (Condo Apartment)

$869900.0

1 +1 Beds
2 Baths
900-999 sq-ft

Top 5 Reasons You Will Love This Condo: 1) Discover one of the final penthouse opportunities in this striking Streetcar Developments residence, design

33 Photos

31 Huron Street, Simcoe, ON , MLS #S12432749 , Image - 1

Unit-412, 31 Huron Street Collingwood, Simcoe, ON MLS® S12432749

Residential Condo & Other (Condo Apartment)

$619900.0

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

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

22 Photos

31 Huron Street, Simcoe, ON , MLS #S12434380 , Image - 1

Unit-209, 31 Huron Street Collingwood, Simcoe, ON MLS® S12434380

Residential Condo & Other (Condo Apartment)

$649900.0

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

Top 5 Reasons You Will Love This Condo: 1) Don't miss your chance to own one of the final remaining fully furnished suites at Harbour House, Collingwo

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

39 Photos

81 Winters Crescent, Simcoe, ON , MLS #S12214004 , Image - 1

81 Winters Crescent Collingwood, Simcoe, ON MLS® S12214004

Residential Condo & Other (Condo Townhouse)

$609000.0

3 Beds
3 Baths
1400-1599 sq-ft

Modern 3-Bed, 3-Bath, 3-storey townhome built in 2024! Each bedroom has its own dedicated bathroom, making daily routines easier for everyone in the h

44 Photos

5 Anchorage Crescent, Simcoe, ON , MLS #S12386017 , Image - 1

Unit-102, 5 Anchorage Crescent Collingwood, Simcoe, ON MLS® S12386017

Residential Condo & Other (Condo Apartment)

$599999.0

2 Beds
2 Baths
1000-1199 sq-ft

Welcome to 5 Anchorage, Unit 102, a beautifully appointed ground-floor condo in the sought-after waterfront community of Wyldewood Cove. This 2-bedroo

50 Photos

6 BRANDY LANE Drive, Simcoe, ON , MLS #S12339205 , Image - 1

Unit-208, 6 BRANDY LANE Drive Collingwood, Simcoe, ON MLS® S12339205

Residential Condo & Other (Condo Apartment)

$549000.0

Price drop by 5.2%

3 Beds
2 Baths
1200-1399 sq-ft

Stylish End Unit in Wyldewood! Your 4-Season Escape! Welcome to this beautifully upgraded 3-bed, 2-bath end unit in the sought-after Wyldewood communi

47 Photos

38 Lighthouse Lane E, Simcoe, ON , MLS #S12437197 , Image - 1

38 Lighthouse Lane E Collingwood, Simcoe, ON MLS® S12437197

Residential Condo & Other (Condo Townhouse)

$1699000.0

4 Beds
3 Baths
2500-2749 sq-ft

This is a RARE + EXCEPTIONAL property-an absolute gem w/ nothing comparable in all of Collingwood. Experience waterfront living at its finest in this

47 Photos

74 Kari Crescent, Simcoe, ON , MLS #S12400750 , Image - 1

74 Kari Crescent Collingwood, Simcoe, ON MLS® S12400750

Residential Condo & Other (Condo Townhouse)

$1299000.0

4 Beds
3 Baths
1400-1599 sq-ft

This beautifully maintained 4-bedroom, 3-bath bungalow blends comfort, style, and functionality. The open-concept kitchen, dining, and living area is

35 Photos

4 Kimberly Lane

Unit-518, 4 Kimberly Lane Collingwood, Simcoe, ON MLS® S12533272

Residential Condo & Other (Condo Apartment)

$774000.0

2 Beds
2 Baths
1000-1199 sq-ft

Penthouse living at the brand new Royal Windsor! If you've been waiting for the best suite in the building, here it is. Suite 518 is a bright, open co

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

OPEN HOUSE: December 20th 1pm-4pm - Christmas on Collins Street!! Your new home awaits in this highly desirable family friendly neighbourhood! Ideall

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)

$429000.0

Price drop by 23.3%

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

27 Photos

80 Huron Street, Simcoe, ON , MLS #S12496276 , Image - 1

80 Huron Street Collingwood, Simcoe, ON MLS® S12496276

Residential Freehold (Detached)

$504000.0

Price drop by 9.8%

3 Beds
2 Baths
1100-1500 sq-ft

POWER OF SALE. 3 Bedroom 1.5 Storey Home. Fully Fenced 54 ft X 175 ft Back Yard. Minutes To Georgian Bay And Downtown Collingwood. A Short Drive To B

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

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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