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Houses for Sale in Grey Highlands ON Under $500K

Showing results 1 - 30 of 38

Are you looking for houses under $500k for sale in Grey Highlands ON? Square Yards Canada offers a wide selection of properties that cater to various budgets in Grey Highlands. Browse through detailed listings with HD images and guides to find the ideal property that fits your budget and preferences in Grey Highlands. Whether you’re looking to buy houses under under $500k in Grey Highlands 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 Grey Highlands houses for sale under under $500k, including freehold homes, condos, and commercial properties.

Last Updated: September 26, 2026

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111 STONEBROOK Way Grey Highlands, Grey County, ON MLS® X13773706

Residential Freehold (Att/Row/Townhouse)

$499900.0

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

Beautiful Townhouse In Markdale. Double Car Garage. Main Floor Features 9 Ft Ceiling. Finished Basement With 2 Bedrooms And A 3 Piece Bath.35 Minutes

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154 Bowles Bluff Road Grey Highlands, Grey County, ON MLS® X13467932

Residential Freehold (Detached)

$400000.0

Price drop by 68.0%

3 Beds
3 Baths
1500-2000 sq-ft

A rare opportunity to secure a premium building lot within walking distance of Beaver Valley Ski Club and create a custom retreat tailored to your lif

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Reg Comp Plan 828 Lot 2 Flewelling Road, Grey County, ON , MLS #X13827390 , Image - 1

Reg Comp Plan 828 Lot 2 Flewelling Road Grey Highlands, Grey County, ON MLS® X13827390

Residential Freehold (Vacant Land)

$169900.0

Discover a rare opportunity to create your own retreat on beautiful Lake Eugenia. This private waterfront building lot offers approximately 75 feet of

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104 Isla Street, Grey County, ON , MLS #X13437248 , Image - 1

104 Isla Street Grey Highlands, Grey County, ON MLS® X13437248

Residential Freehold (Detached)

$389000.0

Price drop by 4.9%

3 Beds
2 Baths
2000-2500 sq-ft

Built in 1900 and located in the growing, vibrant community of Markdale, this 3-bedroom, 2-bathroom home is rich in character, history, and potential.

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320035 170 Road, Grey County, ON , MLS #X13772456 , Image - 1

320035 170 Road Grey Highlands, Grey County, ON MLS® X13772456

Residential Freehold (Detached)

$498888.0

2 +1 Beds
2 Baths
1100-1500 sq-ft

**RARE 3-ACRE OPPORTUNITY IN GREY HIGHLANDS!** Discover privacy, tranquility & incredible potential at **320035 170 Road**, located just minutes south

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349749 4th Concession B N/A, Grey County, ON , MLS #X13810142 , Image - 1

349749 4th Concession B N/A Grey Highlands, Grey County, ON MLS® X13810142

Residential Freehold (Vacant Land)

$499000.0

Vacant Land - 60 wooded/treed acres south of Singhampton. Ideal location to build a home/retreat with easy access to the city, Collingwood etc. Proper

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162 Main Street E, Grey County, ON , MLS #X13204216 , Image - 1

162 Main Street E Grey Highlands, Grey County, ON MLS® X13204216

Residential Freehold (Detached)

$399900.0

Price drop by 6.6%

2 Beds
2 Baths
700-1100 sq-ft

Bungalows like this continue to make sense for a lot of buyers. The layout is practical, the lot is a great size, and the location puts you close to e

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103 Bowles Bluff Road, Grey County, ON , MLS #X13801244 , Image - 1

103 Bowles Bluff Road Grey Highlands, Grey County, ON MLS® X13801244

Residential Freehold (Vacant Land)

$398000.0

< 700 sq-ft

Full 1 Building Acre Lot! Welcome to Bowles Bluff Rd. An excited opportunity to craft your own home on this remarkable 110 x 328 ft lot. Walking dista

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280131 Artemesia-Southgate Townline, Grey County, ON , MLS #X13568970 , Image - 1

280131 Artemesia-Southgate Townline Grey Highlands, Grey County, ON MLS® X13568970

Residential Freehold (Detached)

$405000.0

Price drop by 3.5%

2 Beds
1 Baths
1100-1500 sq-ft

Thoughtfully renovated from top to bottom, this charming bungalow offers the perfect blend of modern comfort, timeless style, and easy one-level livin

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154600 Grey Road 32 N/A, Grey County, ON , MLS #X13756420 , Image - 1

154600 Grey Road 32 N/A Grey Highlands, Grey County, ON MLS® X13756420

Residential Freehold (Detached)

$499000.0

3 Beds
2 Baths
1100-1500 sq-ft

Once Vandeleur's Foresters Hall and now an adorable 1,328 sq ft country home, this one is full of character and in a location that's hard to beat, jus

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LOT 22 Park Street S, Grey County, ON , MLS #X13764392 , Image - 1

LOT 22 Park Street S Grey Highlands, Grey County, ON MLS® X13764392

Residential Freehold (Vacant Land)

$175000.0

Build your dream home or cottage in the quaint town of Eugenia. This .50 acre treed lot is on a quiet street with 132 ft frontage x 165 ft depth and o

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PT LT 2 Lakewood Lane, Grey County, ON , MLS #X13162768 , Image - 1

PT LT 2 Lakewood Lane Grey Highlands, Grey County, ON MLS® X13162768

Residential Freehold (Vacant Land)

$389900.0

There's something about waking up to the glistening water of a lakefront property that instantly makes you feel more relaxed. From quiet mornings with

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135 Isla Street, Grey County, ON , MLS #X13746468 , Image - 1

135 Isla Street Grey Highlands, Grey County, ON MLS® X13746468

Residential Freehold (Detached)

$350000.0

3 Beds
1 Baths
2000-2500 sq-ft

A great opportunity for the first-time buyer, investor or contractor! This 1.5-storey home is move-in ready while you create, update and renovate. It

38 Photos

30 Campbell St Street, Grey County, ON , MLS #X13672596 , Image - 1

30 Campbell St Street Grey Highlands, Grey County, ON MLS® X13672596

Residential Freehold (Detached)

$389000.0

0 +3 Beds
1 Baths
1100-1500 sq-ft

Welcome to this great starter home! Offering plenty of updates, including a 2020 roof and deck, 2015 furnace, 2017 central air, 2021 eavestroughs, fre

33 Photos

13 Collingwood Street, Grey County, ON , MLS #X13037100 , Image - 1

13 Collingwood Street Grey Highlands, Grey County, ON MLS® X13037100

Residential Freehold (Detached)

$385000.0

Price drop by 12.2%

3 Beds
2 Baths
2000-2500 sq-ft

The Oscar Phillips House is one of those homes people already feel connected to before they ever step inside. Sitting proudly at the top of the hill,

36 Photos

27 Herbert Avenue, Grey County, ON , MLS #X13138632 , Image - 1

27 Herbert Avenue Grey Highlands, Grey County, ON MLS® X13138632

Residential Freehold (Detached)

$499000.0

Price drop by 9.1%

3 Beds
2 Baths
700-1100 sq-ft

Fantastic 3 bedroom bungalow, move-in ready. Newer kitchen, newer kitchen appliances, newer main level bathroom. Large picture window in living room,

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PT LT 13 Grey Road 4 N/A, Grey County, ON , MLS #X13691584 , Image - 1

PT LT 13 Grey Road 4 N/A Grey Highlands, Grey County, ON MLS® X13691584

Residential Freehold (Vacant Land)

$100000.0

13 acre property on Grey Road 4 between Flesherton and Priceville. With approximately 869' frontage on the road and the property backing on to the for

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405009 Grey 4 Road, Grey County, ON , MLS #X12908198 , Image - 1

405009 Grey 4 Road Grey Highlands, Grey County, ON MLS® X12908198

Residential Freehold (Detached)

$439900.0

Price drop by 10.0%

1 Beds
1 Baths
700-1100 sq-ft

This adorable like new bungalow in lovely Priceville is full of charm and comfort, Completely updated from top to bottom, its ready for you to move r

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209 Evans Street, Grey County, ON , MLS #X13618694 , Image - 1

209 Evans Street Grey Highlands, Grey County, ON MLS® X13618694

Residential Freehold (Detached)

Price On Request

3 Beds
1 Baths
1100-1500 sq-ft

Discover this newly renovated, well-maintained 3-bedroom detached bungalow in the desirable Grey Highlands community. Bright, inviting living spaces a

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194588 Grey Road 13 N/A, Grey County, ON , MLS #X13513728 , Image - 1

194588 Grey Road 13 N/A Grey Highlands, Grey County, ON MLS® X13513728

Residential Freehold (Vacant Land)

$299000.0

Price drop by 9.1%

700-1100 sq-ft

Build the lifestyle you've always imagined in the heart of Beaver Valley. Set on just over one acre, this beautiful 145' x 300' property offers an inc

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Lot 8 Green Acres Road, Grey County, ON , MLS #X13008300 , Image - 1

Lot 8 Green Acres Road Grey Highlands, Grey County, ON MLS® X13008300

Residential Freehold (Vacant Land)

$385000.0

Lake Eugenia Waterfront access is included in this 100 x 318 lot. On the corner of Grey Road 13 and Green Acres, this property enjoys access on a priv

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405014 Grey Road 4 N/A, Grey County, ON , MLS #X13458802 , Image - 1

405014 Grey Road 4 N/A Grey Highlands, Grey County, ON MLS® X13458802

Residential Freehold (Detached)

$497000.0

2 Beds
1 Baths
700-1100 sq-ft

Brick bungalow with attached garage in Priceville. New bathroom, new lighting, new breaker panel, freshly painted - this home has modern touches and i

28 Photos

116 Main Street W, Grey County, ON , MLS #X13447502 , Image - 1

116 Main Street W Grey Highlands, Grey County, ON MLS® X13447502

Residential Freehold (Detached)

$487000.0

Price drop by 3.9%

2 Beds
2 Baths
1500-2000 sq-ft

Looking for the perfect home for you and your family? Live close to all the amenities in this charming two-bedroom house. Enjoy the convenience of bei

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PT LT27 GREY ROAD 13 N/A, Grey County, ON , MLS #X13242192 , Image - 1

PT LT27 GREY ROAD 13 N/A Grey Highlands, Grey County, ON MLS® X13242192

Residential Freehold (Vacant Land)

$499000.0

6.195 acres of vacant land in stunning Beaver Valley close to the villages of Eugenia and Kimberly and a few mins from Beaver Valley Ski Club and Lake

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Lot 84 Markdale Meadows Drive, Grey County, ON , MLS #X13640286 , Image - 1

Lot 84 Markdale Meadows Drive Grey Highlands, Grey County, ON MLS® X13640286

Residential Freehold (Detached)

$490000.0

3 Beds
3 Baths
1100-1500 sq-ft

To Be Built | Occupancy 2027 | The Tamarack, a beautifully designed 1,500 sq. ft. 2-storey detached home that offers a grounded, realistic path to hom

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Lot 85 Markdale Meadows Drive, Grey County, ON , MLS #X13639900 , Image - 1

Lot 85 Markdale Meadows Drive Grey Highlands, Grey County, ON MLS® X13639900

Residential Freehold (Detached)

$465000.0

3 Beds
3 Baths
1100-1500 sq-ft

To Be Built | Occupancy 2027 | The Tamarack, a beautifully designed 1,300 sq. ft. 2-storey detached home that offers a grounded, realistic path to hom

3 Photos

Pt Lot 80 Grey Road, Grey County, ON , MLS #X13513888 , Image - 1

Pt Lot 80 Grey Road Grey Highlands, Grey County, ON MLS® X13513888

Residential Freehold (Vacant Land)

$214900.0

Located just south of 3rd Concession and Grey Rd this remarkable parcel of land offers an expansive 329.77 feet of frontage and 660.03 deep along Gre

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127 Hunter Street, Grey County, ON , MLS #X13585890 , Image - 1

127 Hunter Street Grey Highlands, Grey County, ON MLS® X13585890

Residential Freehold (Detached)

$459900.0

2 +1 Beds
2 Baths
700-1100 sq-ft

Good Bones! Affordable Living. This 2+1 All Brick Bungalow is the Perfect Start or Perfect Downsize. Updated Eat In Kitchen with Stainless Steel Appli

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Lot 67 Brewester's Lake Road, Grey County, ON , MLS #X12844308 , Image - 1

Lot 67 Brewester's Lake Road Grey Highlands, Grey County, ON MLS® X12844308

Residential Freehold (Vacant Land)

$449000.0

Brewster's Lake vacant land for sale. Perfect setting. 1.43 Acres of land with 135 feet of lake frontage. Homes in the area have sold up to 1.7 millio

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164 John Street Grey Highlands, Grey County, ON MLS® X13527946

Residential Freehold (Vacant Land)

$169900.0

< 700 sq-ft

Live your best rural life inside the brand new home you've built on this prime lot in beautiful grey highlands. Located on a quiet dead end street in

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