320+ Houses for Sale in Collingwood Under $5 Million

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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

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73 Kari Crescent, Simcoe, ON , MLS #S13579440 , Image - 1

73 Kari Crescent Collingwood, Simcoe, ON MLS® S13579440

Residential Condo & Other (Condo Townhouse)

$749000.0

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

Welcome to 73 Kari Crescent, a townhouse offering stylish, low-maintenance living in Collingwood's Balmoral Village. Bright and move-in ready, this ho

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724 Ste Marie Street, Simcoe, ON , MLS #S13651184 , Image - 1

724 Ste Marie Street Collingwood, Simcoe, ON MLS® S13651184

Residential Freehold (Link)

$675000.0

3 +1 Beds
3 Baths
1500-2000 sq-ft

Tucked at the end of a quiet cul-de-sac in a prime Collingwood neighbourhood, this sun-drenched 3+1 bedroom, 2.5 bath home is built for family living.

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52 Seventh Street, Simcoe, ON , MLS #S13538274 , Image - 1

52 Seventh Street Collingwood, Simcoe, ON MLS® S13538274

Residential Freehold (Detached)

$749000.0

3 Beds
2 Baths
1100-1500 sq-ft

Perfectly positioned in the heart of downtown Collingwood, this charming home offers the convenience of in-town living with shops, restaurants, cafes,

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783 Johnston Park Avenue, Simcoe, ON , MLS #S13645616 , Image - 1

783 Johnston Park Avenue Collingwood, Simcoe, ON MLS® S13645616

Residential Condo & Other (Condo Townhouse)

$589000.0

3 Beds
2 Baths
1200-1399 sq-ft

Experience the best of waterfront living at Lighthouse Point Yacht & Tennis Club -a highly sought-after community spanning more than 125 acres along t

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42 Silver Crescent, Simcoe, ON , MLS #S13481368 , Image - 1

42 Silver Crescent Collingwood, Simcoe, ON MLS® S13481368

Residential Freehold (Detached)

$1975000.0

Price drop by 6.0%

4 +2 Beds
4 Baths
2000-2500 sq-ft

Welcome to this spectacular bungaloft overlooking Georgian Bay in one of Collingwood's most desirable neighbourhoods. Set on a large beautifully lands

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50 Silver Glen Boulevard, Simcoe, ON , MLS #S13654472 , Image - 1

50 Silver Glen Boulevard Collingwood, Simcoe, ON MLS® S13654472

Residential Condo & Other (Condo Townhouse)

$725000.0

3 Beds
3 Baths
1200-1399 sq-ft

Thoughtfully upgraded four seasons home, minutes to ski hills, scenic trails and downtown Collingwood. Freshly painted throughout, Modern kitchen with

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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

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62 FOLEY Crescent, Simcoe, ON , MLS #S13630356 , Image - 1

62 FOLEY Crescent Collingwood, Simcoe, ON MLS® S13630356

Residential Freehold (Detached)

$1288000.0

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

PREMIUM Corner Lot Backing Onto Mature Trees *Luxury Designer Upgrades *New Composite Deck (2025) *Fully Fenced Yard. An exceptional opportunity to ow

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98 Huron Street, Simcoe, ON , MLS #S13249778 , Image - 1

98 Huron Street Collingwood, Simcoe, ON MLS® S13249778

Residential Freehold (Detached)

$2499000.0

4 +2 Beds
4 Baths
3000-3500 sq-ft

Victorian Elegance Meets Georgian Bay Waterfront Living! Breathtaking custom-built home overlooking Sunset Point and the sparkling waters of Georgian

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16 Carmichael Crescent, Simcoe, ON , MLS #S13634656 , Image - 1

16 Carmichael Crescent Collingwood, Simcoe, ON MLS® S13634656

Residential Freehold (Detached)

$1299000.0

4 +1 Beds
4 Baths
2500-3000 sq-ft

Completely Renovated Luxury Family Home in Sought-After Lockhart Subdivision! Welcome to this exceptional move-in ready home, backing onto Kinsmen Par

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835 Suncrest Circle, Simcoe, ON , MLS #S13041774 , Image - 1

835 Suncrest Circle Collingwood, Simcoe, ON MLS® S13041774

Residential Condo & Other (Condo Townhouse)

$699000.0

Price drop by 6.8%

3 Beds
3 Baths
1200-1399 sq-ft

Lighthouse Point Yacht and Tennis Club- a community that embraces the 4 seasons lifestyle! Bright & Renovated corner end unit w/3 bedrooms/3 bathrooms

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2 Ramblings Way

Unit-8, 2 Ramblings Way Collingwood, Simcoe, ON MLS® S13416472

Residential Condo & Other (Condo Townhouse)

$519000.0

Price drop by 2.1%

2 Beds
2 Baths
900-999 sq-ft

Waterfront!!!Live Like You're on Vacation Every Day at Ruperts Landing! Welcome to Ruperts Landing, one of Collingwood's most desirable gated waterfro

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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

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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

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100 Kari Crescent, Simcoe, ON , MLS #S13652724 , Image - 1

100 Kari Crescent Collingwood, Simcoe, ON MLS® S13652724

Residential Condo & Other (Condo Townhouse)

$1199000.0

3 +1 Beds
4 Baths
1800-1999 sq-ft

Welcome to Balmoral Village-one of Collingwood's most sought-after communities, thoughtfully designed for an active and social 55+ lifestyle. This bea

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103 Plewes Drive W, Simcoe, ON , MLS #S13647650 , Image - 1

103 Plewes Drive W Collingwood, Simcoe, ON MLS® S13647650

Residential Freehold (Detached)

$1035000.0

4 Beds
3 Baths
2000-2500 sq-ft

A Rare Find in Summitview Community This Devonleigh-built detached home (Premium Lot) in the highly sought-after Summitview Community is a rare find.

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1 Hume Street, Simcoe, ON , MLS #S13652562 , Image - 1

Unit-PH 615, 1 Hume Street Collingwood, Simcoe, ON MLS® S13652562

Residential Condo & Other (Condo Apartment)

$1549000.0

2 +1 Beds
2 Baths
1400-1599 sq-ft

Welcome to Penthouse 615 at Monaco - a landmark of sophisticated living in historic downtown Collingwood! Experience elevated living in this Architect

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22 Cranberry Surf N/A, Simcoe, ON , MLS #S12919112 , Image - 1

22 Cranberry Surf N/A Collingwood, Simcoe, ON MLS® S12919112

Residential Condo & Other (Condo Townhouse)

$549900.0

3 Beds
3 Baths
1000-1199 sq-ft

With views of Georgian Bay, a neighborhood saltwater pool, and direct access to nature, 22 Cranberry Surf offers the perfect blend of modern comfort a

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130 Fifth Street, Simcoe, ON , MLS #S13639562 , Image - 1

130 Fifth Street Collingwood, Simcoe, ON MLS® S13639562

Residential Freehold (Detached)

$1180000.0

Price drop by 4.1%

3 Beds
3 Baths
1500-2000 sq-ft

Victoria Annex: History Made Modern Nestled in one of Collingwood's most sought-after neighbourhoods, Victoria Annex is a boutique community of just n

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125 Sixth Street, Simcoe, ON , MLS #S13639564 , Image - 1

125 Sixth Street Collingwood, Simcoe, ON MLS® S13639564

Residential Freehold (Detached)

$1194000.0

Price drop by 4.0%

3 +1 Beds
4 Baths
1500-2000 sq-ft

Victoria Annex: History Made Modern nestled in one of Collingwood's most sought-after neighbourhoods. A rare opportunity in a limited collection of si

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173 Vacation Inn Drive, Simcoe, ON , MLS #S13584960 , Image - 1

173 Vacation Inn Drive Collingwood, Simcoe, ON MLS® S13584960

Residential Condo & Other (Condo Townhouse)

$544900.0

3 +0 Beds
3 Baths
1200-1399 sq-ft

End unit with SOUTH/ WEST EXPOSURE and PRIVACY! MINUTES TO THE SKI HILL and GEORGIAN BAY. 3 Bed/3 Bath1250 S.f. Home- Fully Furnished. 2 PARKING SPOTS

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94 KIRBY Avenue, Simcoe, ON , MLS #S13645792 , Image - 1

94 KIRBY Avenue Collingwood, Simcoe, ON MLS® S13645792

Residential Freehold (Detached)

$949900.0

4 +0 Beds
3 Baths
2000-2500 sq-ft

Welcome to a masterpiece of modern living where luxury meets nature in every corner of this stunning residence! With over $ 50K in premium upgrades an

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36 Georgian Meadows Drive, Simcoe, ON , MLS #S13537830 , Image - 1

36 Georgian Meadows Drive Collingwood, Simcoe, ON MLS® S13537830

Residential Freehold (Detached)

$989900.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 36 Georgian Meadows! A fabulous executive 4 bedroom home in a wonderful family neighbourhood in Collingwood. Main floor was fully renovated

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63 BROADVIEW Street, Simcoe, ON , MLS #S13534242 , Image - 1

63 BROADVIEW Street Collingwood, Simcoe, ON MLS® S13534242

Residential Freehold (Detached)

$1199000.0

Price drop by 2.1%

7 Beds
3 Baths
3500-5000 sq-ft

Discover the perfect layout for multi-generational living in this impressive two-and-a-half-story brick residence. This versatile property features a

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3 DICKSON Road, Simcoe, ON , MLS #S13631530 , Image - 1

3 DICKSON Road Collingwood, Simcoe, ON MLS® S13631530

Residential Freehold (Detached)

$535000.0

3 +1 Beds
1 Baths
700-1100 sq-ft

Fabulous 4 Bedroom raised bungalow with separate entrance to basement level making it an ideal candidate for an accessory apartment (subject to town a

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4 Parkside Avenue, Simcoe, ON , MLS #S13539202 , Image - 1

4 Parkside Avenue Collingwood, Simcoe, ON MLS® S13539202

Residential Freehold (Detached)

$750000.0

4 Beds
1 Baths
1100-1500 sq-ft

Walk to the shores of Georgian Bay from this 4 bedroom bungalow. Open concept kitchen / dining / living room with access to the backyard. Separate fam

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59 Maidens Crescent, Simcoe, ON , MLS #S13440140 , Image - 1

59 Maidens Crescent Collingwood, Simcoe, ON MLS® S13440140

Residential Freehold (Detached)

$1128000.0

5 Beds
4 Baths
2500-3000 sq-ft

Luxurious Two-Story Haven in Picturesque Collingwood, Located in Between Blue Mountain and Beautiful Town of Collingwood with Many Attractions. You Ca