L9Y, ON Houses for Lease Under 500K

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160 Grand Cypress Lane, Grey County, ON , MLS #X14101228 , Image - 1

160 Grand Cypress Lane Blue Mountains, Grey County, ON MLS® X14101228

Residential Freehold (Detached)

$10000.0

4 Beds
5 Baths
3500-5000 sq-ft

SEASONAL LEASE WITH HOT TUB & SAUNA - FLEXIBLE AVAILABILITY. 3 MONTHS CONSIDERED AT A HIGHER MONTHLY RATE. Experience luxury, comfort and adventure at

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38 Dawson Drive, Simcoe, ON , MLS #S14100990 , Image - 1

Unit-83, 38 Dawson Drive Collingwood, Simcoe, ON MLS® S14100990

Residential Condo & Other (Condo Townhouse)

$2800.0

3 Beds
2 Baths
1200-1399 sq-ft

~ ALL INCLUSIVE, FULLY FURNISHED condo townhouse in Collingwood's Escarpment community! ~ Annual Term. Completely renovated in late 2021, this fully f

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31 Huron Street, Simcoe, ON , MLS #S13694672 , Image - 1

Unit-224, 31 Huron Street Collingwood, Simcoe, ON MLS® S13694672

Residential Condo & Other (Condo Apartment)

$3200.0

1 Beds
2 Baths
1000-1199 sq-ft

Luxury Waterfront Living in Collingwood. Welcome to this grand 1200 sq. ft corner unit with panoramic views of Georgian Bay and ski hills, where floor

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67 Shipley Avenue, Simcoe, ON , MLS #S14099660 , Image - 1

Unit-Unit 2, 67 Shipley Avenue Collingwood, Simcoe, ON MLS® S14099660

Residential Freehold (Duplex)

$2200.0

2 Beds
1 Baths
< 700 sq-ft

Step inside and discover comfort and style in this all-inclusive, legal 2-bedroom basement apartment with 2-car parking and a private side yard. Imagi

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2 RAMBLINGS Way, Simcoe, ON , MLS #S14097928 , Image - 1

Unit-9, 2 RAMBLINGS Way Collingwood, Simcoe, ON MLS® S14097928

Residential Condo & Other (Condo Townhouse)

$2300.0

2 +0 Beds
2 Baths
1000-1199 sq-ft

Searching for Your Waterfront Dream? Look No Further! Welcome to Ruperts Landing, an exclusive gated community designed for those who treasure the wat

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25 Kirby Avenue, Simcoe, ON , MLS #S13881042 , Image - 1

25 Kirby Avenue Collingwood, Simcoe, ON MLS® S13881042

Residential Freehold (Att/Row/Townhouse)

$4000.0

Reduced by 75.0%

3 Beds
3 Baths
1100-1500 sq-ft

WINTER SKI SEASON RENTAL - 4-MONTH TERM ($16,000). Welcome to your charming winter getaway at 25 Kirby Avenue! Perfectly positioned just a short drive

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8390 Poplar Side Road, Simcoe, ON , MLS #S14093454 , Image - 1

8390 Poplar Side Road Rural Clearview, Clearview, Simcoe, ON MLS® S14093454

Residential Freehold (Detached)

$28000.0

3 Beds
2 Baths
1500-2000 sq-ft

Beautiful log cabin located in the highly desirable neighbourhood of Collingwoodlands. Winter season rental available for four months at $28,000 Decem

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73 Archer Avenue, Simcoe, ON , MLS #S13833570 , Image - 1

73 Archer Avenue Collingwood, Simcoe, ON MLS® S13833570

Residential Freehold (Semi-Detached )

$4000.0

Reduced by 78.9%

3 Beds
4 Baths
1500-2000 sq-ft

EXCEPTIONAL SKI SEASONAL LEASE. A beautifully appointed winter retreat for those who appreciate quality, comfort and an exceptional location. Tasteful

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31 Huron Street, Simcoe, ON , MLS #S14088838 , Image - 1

Unit-617, 31 Huron Street Collingwood, Simcoe, ON MLS® S14088838

Residential Condo & Other (Condo Apartment)

$1900.0

1 Beds
2 Baths
1000-1199 sq-ft

Seasonal winter rental in Harbour House with flexible dates between November 15 - April 15. Luxury Penthouse condo offers 1 bedroom 2 bath on 2 levels

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209583 26 Highway, Grey County, ON , MLS #X13688458 , Image - 1

209583 26 Highway Blue Mountains, Grey County, ON MLS® X13688458

Residential Freehold (Detached)

$18000.0

Reduced by 30.8%

3 Beds
2 Baths
1100-1500 sq-ft

Bayside Blue: Private Georgian Bay Waterfront with Beach and Hot Tub, 8 Minutes to Blue Mountain. FURNISHED SEASONAL/SKI SEASON RENTAL ($18,000) OR MI

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29 NORTH MAPLE Street, Simcoe, ON , MLS #S13613504 , Image - 1

29 NORTH MAPLE Street Collingwood, Simcoe, ON MLS® S13613504

Residential Condo & Other (Condo Townhouse)

$18000.0

3 +0 Beds
2 Baths
1600-1799 sq-ft

SHIPYARDS WINTER RENTAL! 3 bedrooms, 2.5 baths, warm furniture and decor - turn key condo ready for your family. Spacious primary bedroom + ensuite, c

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178 Brophy's Lane, Grey County, ON , MLS #X13771330 , Image - 1

178 Brophy's Lane Blue Mountains, Grey County, ON MLS® X13771330

Residential Freehold (Detached)

$2750.0

Reduced by 8.3%

3 Beds
2 Baths
1100-1500 sq-ft

Some homes make it very easy to settle in and start enjoying where you live. 178 Brophy's Lane is one of them. Fully furnished and set beneath mature

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471 Oxbow Crescent, Simcoe, ON , MLS #S14090124 , Image - 1

471 Oxbow Crescent Collingwood, Simcoe, ON MLS® S14090124

Residential Condo & Other (Condo Townhouse)

$10000.0

3 Beds
2 Baths
1400-1599 sq-ft

FULLY FURNISHED SEASONAL RENTAL - Available January 1, 2027 to March 31, 2027. Stunning 3 bedroom, 2 bathroom townhouse located in a very quiet neigh

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138 Peel Street, Simcoe, ON , MLS #S14086002 , Image - 1

138 Peel Street Collingwood, Simcoe, ON MLS® S14086002

Residential Freehold (Detached)

$4000.0

3 Beds
2 Baths
1100-1500 sq-ft

SEASONAL LEASE - SKI SEASON 2026/2027 - FLEXIBLE DATES - Winter Living near Downtown Collingwood!Enjoy a stylish winter stay in this 3 bedroom, 2 bath

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34 Lett Avenue, Simcoe, ON , MLS #S13844534 , Image - 1

34 Lett Avenue Collingwood, Simcoe, ON MLS® S13844534

Residential Freehold (Att/Row/Townhouse)

$12000.0

3 Beds
4 Baths
1100-1500 sq-ft

SKI SEASON rental, available Jan 1st to March 31st. Located in he desirable Blue Fairways, a great location to access all the ski hills and Historic D

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230 Grey Road 21 Road, Grey County, ON , MLS #X12949162 , Image - 1

230 Grey Road 21 Road Blue Mountains, Grey County, ON MLS® X12949162

Residential Freehold (Detached)

$5500.0

4 Beds
3 Baths
1500-2000 sq-ft

Enjoy Christmas and New Year's and the build-up to the festive season, in a ten acre winter wonderland setting, minutes from BLUE MOUNTAIN VILLAGE! Th

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20 Beckwith Lane

Unit-401, 20 Beckwith Lane Blue Mountains, Grey County, ON MLS® X13877646

Residential Condo & Other (Condo Apartment)

$2300.0

2 Beds
1 Baths
600-699 sq-ft

WINTER SEASONAL LEASE - Wake up to beautiful views of Blue Mountain and step outside onto your private terrace, with the trails, slopes, and everythin

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148 Sycamore Street, Grey County, ON , MLS #X12907448 , Image - 1

148 Sycamore Street Blue Mountains, Grey County, ON MLS® X12907448

Residential Freehold (Semi-Detached )

$3200.0

3 Beds
3 Baths
1500-2000 sq-ft

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10 Beausoleil Lane, Grey County, ON , MLS #X14031418 , Image - 1

Unit-104, 10 Beausoleil Lane Blue Mountains, Grey County, ON MLS® X14031418

Residential Condo & Other (Condo Apartment)

$5000.0

2 Beds
2 Baths
800-899 sq-ft

Six-Week Seasonal Escape at Mountain House! Available exclusively from November 13 to January 3, this beautifully furnished 2-bedroom, 2-bathroom grou

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2 Cove Court, Simcoe, ON , MLS #S13678698 , Image - 1

Unit-301, 2 Cove Court Collingwood, Simcoe, ON MLS® S13678698

Residential Condo & Other (Condo Apartment)

$8800.0

2 Beds
2 Baths
900-999 sq-ft

Dec 1st to March 31st. Enjoy the winter season in this comfortable and well-equipped 2-bedroom condo, perfect for a seasonal getaway in the Collingwoo

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4594 County Road 124 Road, Simcoe, ON , MLS #S13883528 , Image - 1

4594 County Road 124 Road Rural Clearview, Clearview, Simcoe, ON MLS® S13883528

Residential Freehold (Detached)

$5000.0

3 Beds
2 Baths
1500-2000 sq-ft

SKI SEASON RENTAL - DECEMBER 20TH TO END OF APRIL | FLEXIBLE DATES-Enjoy the perfect winter getaway in Clearview, just steps from Collingwood and clos

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10 NIAGARA Street, Simcoe, ON , MLS #S13726024 , Image - 1

10 NIAGARA Street Collingwood, Simcoe, ON MLS® S13726024

Residential Freehold (Detached)

$20000.0

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

Winter Rental Rate for 4 months, $20,000. Also available for lease immediately until the end of June for $3900. A rare opportunity for the Collingwood

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63 Georgian Manor Drive, Simcoe, ON , MLS #S13884634 , Image - 1

63 Georgian Manor Drive Collingwood, Simcoe, ON MLS® S13884634

Residential Freehold (Detached)

$6000.0

5 Beds
3 Baths
3000-3500 sq-ft

YOUR LUXURY SKI SEASON RETREAT ON GEORGIAN BAY! Experience the ultimate winter getaway in this spectacular 3,300 sq. ft. custom-built waterfront home,

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190 Stoneleigh Drive, Grey County, ON , MLS #X14011128 , Image - 1

190 Stoneleigh Drive Blue Mountains, Grey County, ON MLS® X14011128

Residential Freehold (Semi-Detached )

$3200.0

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

Welcome to 190 Stoneleigh, a stunning brand-new semi-detached home offering modern comfort and four-season living in the heart of the Blue Mountain ar

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329 MARINERS Way, Simcoe, ON , MLS #S13603504 , Image - 1

329 MARINERS Way Collingwood, Simcoe, ON MLS® S13603504

Residential Condo & Other (Condo Townhouse)

$2900.0

Reduced by 3.3%

2 +0 Beds
2 Baths
800-899 sq-ft

Welcome to Lighthouse Point, one of Collingwood's premier waterfront communities, available for the full ski season (flexible dates). Dec-March is $12

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104 Kinsey Place, Grey County, ON , MLS #X13783988 , Image - 1

104 Kinsey Place Blue Mountains, Grey County, ON MLS® X13783988

Residential Freehold (Detached)

$10000.0

2 Beds
3 Baths
1500-2000 sq-ft

Winter Seasonal Rental - 3-Month Price - in the Heart of Blue Mountain- Steps to South Base Lodge & Village! Experience the best of fall and winter in

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55 CLUBHOUSE Drive, Simcoe, ON , MLS #S13818528 , Image - 1

55 CLUBHOUSE Drive Collingwood, Simcoe, ON MLS® S13818528

Residential Condo & Other (Detached Condo)

$2988.0

Reduced by 6.3%

2 +0 Beds
2 Baths
1000-1199 sq-ft

ANNUAL LEASE available November 1st, 2026! Also available for SEASONAL LEASE (unfurnished) for $3300/m. Enjoy Collingwood living at its finest in the

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183 ALTA Road, Grey County, ON , MLS #X13109960 , Image - 1

183 ALTA Road Blue Mountains, Grey County, ON MLS® X13109960

Residential Freehold (Detached)

$6475.0

Reduced by 83.2%

4 Beds
4 Baths
2500-3000 sq-ft

Available for ski season, $25,900. TURN KEY SEASONAL RENTAL. December 2026 - March 2027.Steps from Alpine Ski Club. Discover the ultimate seasonal ret