Real Estate Photography Listings in Grey Highlands

385073 4TH CONCESSION A, Grey Highlands

Type: Single Family

Land: 1324.1 x 3325.7 FT|50 - 100 acres

Price: $3,350,000.00

Refined, relaxed, and completely unforgettable, 99.6-acre estate blends high-end country living with thoughtful design in every square foot. At its heart is a custom post and beam home by Yankee Barn Homes, inspired by the timeless, lived-in style of Ina Garten. Soaring Douglas fir beams, wide-open living spaces, and curated details set the tone for a home that's both elegant and entirely unpretentious. The kitchen and dining area is a true showstopper: two storeys high, anchored by a Rumford wood-burning fireplace, and designed for gathering. From the beautiful front foyer to the luminous living spaces throughout, everything feels welcoming, warm, and easy to love. The main floor features a luxurious primary suite, powder room, laundry, and direct access to an oversized triple-plus garage, making single-floor living a seamless option. Upstairs, there's room for everyone: a private bedroom with an ensuite, a cozy bunk room, another full bath, and a flexible loft for movie nights or quiet corners. A fourth bedroom, family room with projector and screen, full bath, and kitchenette round out the space perfect for multi-generational living or guests who like to stay awhile. The lower level walkout brings even more: a stylish bar and rec space, fifth bedroom, second laundry, full bath, and a cold cellar for your wine or preserves. Outside, the saltwater pool by Dream Pools of Oakville is ready for laid-back summer days and outdoor entertaining. The land itself offers a rare mix of 60 acres of working farmland, a 5-acre natural pond, a spring-fed fishing pond, and a 20-acre hardwood bush that's as beautiful as it is useful. A classic bank barn and detached garage complete the picture. This is more than a home; it's a legacy property designed for comfort, connection, and countryside living at its finest. (39939190)

144 TALISMAN BOULEVARD, Grey Highlands

Type: Single Family

Land: 270.5 x 132 FT|under 1/2 acre

Price: $998,000.00

Looking for a place where your weekend adventures can turn into lifelong memories? This 5 bedroom, 2.5 bath chalet near Kimberley is built for just that, ski days, summer nights, & everything in between. With three fully finished levels, there's room for everyone to spread out, relax, & make themselves at home. The walkout lower level is made for après-ski life: drop your gear in the spacious mudroom, kick back in the family room or games area, and give guests (or teenagers) their own space with a fifth bedroom & 3-piece bath. The main floor is where the action happens, an open-concept layout, framed by large windows & sliding doors that lead to both front & back decks. Entertain with ease thanks to the wet bar & convenient 2-piece bath. Whether it's casual get-togethers or full-on holiday gatherings, this place makes hosting feel effortless. Upstairs, you'll find four more bedrooms & a full bath, with two bedrooms opening to a private upper deck ideal for morning coffee, a quiet read, or catching the stars after a day of adventure. The outdoor setup is just as inviting: soak in the hot tub, step into the wood-fired sauna, or cozy up around the firepit under the trees. Whether you're here full-time, visiting for the weekend, or offering short-term stays (STA licensed, buyer to reapply), the setting is ready for all-season living. Just minutes from the heart of Kimberley, and close to Thornbury & Meaford, you're never far from great food, good coffee, or a bit of small-town charm. Skiing, hiking, and nature are all right here, making this chalet not just a home but a basecamp for everything you love to do. (39615421)

795099 EAST BACK LINE, Grey Highlands

Type: Single Family

Land: 405.5 x 290.3 FT|2 - 4.99 acres

Price: $995,000.00

This isn't just a home; it's a lifestyle waiting to be lived. Tucked away on 2.7 acres of gorgeous countryside, this timeless red brick Victorian blends charm, character, and comfort in all the right ways. Whether you're craving a full-time move or a weekend escape, this property is the perfect mix of peaceful retreat and everyday practicality. Inside, the layout is both functional and full of personality. You'll find 4 bedrooms and 2 full baths, an updated kitchen warmed by a woodstove, and a sunlit breakfast nook that opens to your own private side yard, ideal for coffee, cocktails, or watching the seasons change. The separate dining room is made for lively dinners and celebrations, while the cozy living room gives everyone their own space to unwind. The real wow-factor? A beautiful 2-storey timber frame addition that brings the outdoors in, with a great room that overlooks the gardens and an upper-level primary suite you may never want to leave. Outside, you'll fall in love with the peaceful courtyard and decorative pond, a quiet pocket of calm that feels like your own little secret. There's also a handy main floor office, laundry room, and an attached garage for everyday convenience. For hobbyists, tinkerers, or anyone who needs extra room, the detached garage with workshop offers plenty of space to create or store. There's even a charming old barn and a greenhouse ready for your gardening plans or future ideas. Set on a paved road just minutes from Markdale and only 5 minutes to the top of BVSC, this home is close to everything but feels like a world away. It's the kind of place that catches your eye and stays on your mind. Curious yet? You should be. Homes like this don't come along every day. (40208097)

825141 GREY ROAD 40 ROAD, Grey Highlands

Type: Vacant Land

Land: 591.78 x 1979.91 M|25 - 50 acres

Price: $699,999.00

Looking for an "off the grid" recreational property with potential? Look no further then this easily accessible and well located property in Grey Highlands at 26.7 acres. The area is home to dozens of trails & Managed Areas and offers great four season activities. 20 minutes to Thornbury 15 minutes to Markdale or 25 minutes to the Village at Blue Mountain. (39865643)

429570 8TH B CONCESSION ROAD, Grey Highlands

Type: Vacant Land

Land: 228 x 498 FT|2 - 4.99 acres

Price: $450,000.00

Private 2 Acre lot on a well maintained country road just 3 Km from Singhampton(The Hamptons). Elevated building envelope is partially cleared. Driveway is installed. Land survey has been completed. Build your rural retreat or getaway chalet amongst gentle nature, mature cedar and wild apple trees in this quiet location close to quaint villages, downtown Collingwood and the ski hills of Devils Glen, Beaver Valley Ski Club, Blue Mountain. Exactly a scenic 20 minute drive into Collingwood proper. Fresh air and clean living, greener pastures do exist! Reputable Builders incentives available. (39626111)