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Grey Highlands is a municipality in the southeast corner of Grey County, Ontario, Canada. It was formed on January 1, 2001, by the amalgamation of the village of Markdale and the townships of Artemesia, Euphrasia and Osprey, which included the unincorporated hamlets of Eugenia, Ceylon, Maxwell, Singhampton, Priceville, Kimberley, Badjeros, and Feversham. The former village of Flesherton is also located within the municipality and was amalgamated with Artemesia Township in 1998.
The dominant natural feature of the area is the Niagara Escarpment, which passes through the municipality and has several ancillary features:
the Bruce Trail, a popular hiking and multi-use trail, follows the brow of the Niagara Escarpment.
Beaver Valley, a steep-sided and broad valley, was created during the last ice age. The eastern side of the valley, as part of the Niagara Escarpment, was designated a UNESCO Biosphere reserve in 1990. The west side of the valley is home to a number of downhill ski slopes, including Beaver Valley Ski Club.
Eugenia Falls, where the Beaver River crosses the Niagara Escarpment, is the location of Grey County's only gold rush.
Total Active Listings in Municipality of Grey Highlands: 13
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)
142 LAKESHORE BOULEVARD, Lake Eugenia
Type: Single Family
Land: 44.4 x 172.9 FT|under 1/2 acre
Price: $1,895,000.00
Sunset views, easy water access, & a home that brings the lakefront lifestyle to life, that's what you'll find in this well-built year-round cottage or full-time home on Lake Eugenia. With 169' of pristine west-facing shoreline, you'll soak in some of the most beautiful sunsets the lake has to offer. Built in 2002, this thoughtfully designed bungalow offers 2+2 bedrooms, 2 full baths, & a fully finished walkout lower level with lake views from almost every room in the house. From the stillness of a snowy lake view through the windows to warm summer afternoons spent on the tiered waterfront deck, there's a calm that settles over you--that unmistakable feeling of being on the water. The living room features a cathedral ceiling, a cozy propane fireplace, and stunning water views through large windows that frame the ever-changing lake-like artwork. Both the dining area & the primary bedroom offer their own private decks overlooking the lake, perfect for morning coffee, evening drinks, or simply taking it all in. Downstairs, 9' ceilings, a woodstove, & walkout access make the lower level just as comfortable, with plenty of space for guests, games, or quiet downtime. Outside, it's set up for classic lake life: a wooden kayak/canoe ramp, concrete launch, & marine railway boat system make getting on the water easy. Mature trees, apple trees, & flower gardens give the property a natural, well-loved feel. And with a detached double garage, you've got space for all the tools, toys, or hobby gear you need. Whether you're after peaceful mornings, paddleboard afternoons, sunset cocktails by the shore, or après-ski evenings, this property delivers the lakefront lifestyle with comfort, style, & space to truly enjoy it. (40208322)
408082 GREY 4 ROAD, Maxwell
Type: Single Family
Land: 230.2 x 452.5 Acre|2 - 4.99 acres
Price: $1,750,000.00
Experience the best of both worlds where this masterpiece creates a country charm that blends perfectly with new, modern and luxurious. Set on 2 acres of peaceful, pastoral views this recently renovated home offers exactly that. Upon entering through classic side porch you're greeted by a warm & inviting interior with exquisite finishes to behold. Approx 2800 sq ft of tasteful, elegant yet practical features like wide plank wood flooring, exposed ceiling beams, rustic barn door enhancements to closets and windows, hi end fixtures and finishes are found throughout. Open concept layout where the extraordinary rustic gourmet kitchen lays central in the floor plan. Here it boasts the vaulted ceiling with exposed wood beams, custom maple cabinetry, granite countertops, 9' chefs island, butlers pantry and a coffee and wine bar. Kitchen flows to both the dining room big enough to host the entire family and a wonderfully large family room with fireplace and walkout to side patio. The primary bedroom is a bright, sunny retreat complete with a 5 pc ensuite, a walk in closet & its own access to relax on the back yard patio with pergola. A 2nd bedroom, laundry room, office area, some flex space and a powder room finish the main floor. Original refinished pine flooring on the second floor where an ample sized guest bedroom with its own 4 pc bath is found. Attached 1200 sq ft heated & insulated garage has inside entry to home. Seamless indoor outdoor flow to several patios where they're placed to enjoy the quiet serenity of the countryside. This property offers upscale living in a quiet rural village. Come see to appreciate the 10+ craftsmanship and elegant style this true gem has to offer. Close to Lake Eugenia, the Beaver Valley and only 25 minutes to Collingwood. (38137704)
222 PLANTTS POINT ROAD, Lake Eugenia
Type: Single Family
Land: 210 x 235.8 FT ; comes to point at waterfront|1/2 - 1.99 acres
Price: $1,699,000.00
Your waterfront summer (& winter) escape awaits! Dreaming of days spent by the lake or close to the slopes? This stunning waterfront property is your ticket to a perfect summer getaway AND a fantastic winter retreat. Imagine spending sun-drenched days on Lake Eugenia & then come winter, embracing the thrill of skiing just minutes away. This isn't just a cottage; it's a 4 season haven. Picture yourself on the water all summer long, enjoying the child-friendly shoreline & making the most of the dock + boathouse complete with a rooftop patio perfect for those sunset cocktails! Come winter, swap your boat for skis & hit the slopes at Beaver Valley or Blue Mountain-they're practically in your backyard. With over 3000 sq ft of finished living space including a show-stopping Great Room, there's plenty of space for family & friends. The luxurious hot tub overlooking the lake is the perfect spot to relax year-round, whether unwinding after skiing or enjoying a starlit summer night. Create warm memories gathering around the fire pit for marshmallow roasts or fireplace after a cold day outside. This property offers the perfect balance of summer relaxation & winter adventure. Located in the heart of Ontario's outdoor playground, you'll have easy access to it all. Warm weather bring boating, swimming, hiking & golf while snow transforms the area into a skier's paradise. With activities just minutes away you'll spend less time travelling & more time doing your favourite things. Conveniently located less than 2hrs from GTA, 90 mins from Kitchener-Waterloo, Barrie & Guelph, 30mins from Collingwood/Thornbury and the charming villages of Kimberley, Flesherton & Markdale all nearby, this property offers the perfect blend of tranquility & accessibility for both summer & winter getaways. Don't let the chance of a summer by the lake slip away & don't wait until next winter to hit the slopes. This is your chance to own a piece of waterfront paradise that you can enjoy all year round! (39929617)
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)
Welcome to the latest community by Devonsleigh Homes. This Craftsman Villa end-unit town is only connected to the neighbour by garage wall. Appreciate the price point of a townhouse while enjoying the feel of detached living. This end unit location allows for extra natural light on three sides of the home, enhancing its airy, bright feel. Upon entering, you're greeted by high ceilings and modern finishes. The living room is spacious with hardwood floors and features large windows, patio door walk out to yard & open concept to the kitchen & eat in area.Upstairs, youll find three generously sized bedrooms, each with large windows that provide lovely views of the surrounding area. The master suite includes a walk-in closet and a private en-suite bathroom, featuring a modern walk-in shower and a double vanity. The two additional bedrooms are ideal for children, guests, or even as a home office, and they share a well-appointed second bathroom with a tub/shower combination. This house is the perfect blend of modern living, privacy and charm, offering a cozy yet spacious home for those looking to settle in a small-town community. The quiet streets gives a suburban feel, with easy access to local parks, shops, schools, and restaurants offering a perfect balance of comfort and accessibility (68765468)
326129 3RD CONCESSION ROAD, Port Law
Type: Single Family
Land: 96 x 113.5 FT|under 1/2 acre
Price: $659,000.00
Tucked into the quiet hamlet of Port Law, in Grey Highlands this beautifully updated country bungalow offers a fantastic blend of modern finishes & timeless rural comfort. Set on a peaceful 1/4 acre lot surrounded by mature trees & backing onto open farmland, this is the kind of place where life slows down & gets a little sweeter. From the moment you arrive, there's a welcoming feel. Step through the front mudroom & into the heart of the home, an open-concept kitchen & living area designed for everyday ease & connection. The kitchen features stainless steel appliances, a stylish backsplash, & a centre island with a breakfast bar, all flowing effortlessly into the living space. South-facing windows bring in the light, creating a warm & inviting atmosphere throughout the day. There are three comfortable bedrooms. The primary suite offers a private 3-piece ensuite with a sleek stand-up shower, while a modern 4-piece bath serves the rest of the home. With easy-care vinyl plank flooring, a propane furnace, pellet stove, and R60 insulation, comfort and efficiency are built right in. Step out to the deck, the perfect spot to enjoy your morning coffee surrounded by the peaceful sounds of nature or to unwind in the evening beneath the breathtaking hues of a glowing Grey County sunset. The front flower beds add a welcoming touch of colour to the landscape, while the 18'x24'6" hobby barn, complete with a loft with hydro, offers endless possibilities. Whether you envision a creative studio, workshop, home office, or the ultimate getaway space, this versatile outbuilding is ready to bring your ideas to life. Just 15 minutes from shopping in Markdale or Dundalk, 8 minutes to Lake Eugenia, nearby waterfalls, trails, & snowmobile routes, with Blue Mountain just over half an hour away this is where small-town charm meets year-round adventure. Whether you're starting out, slowing down, or simply craving the peace of country life, this one-of-a-kind haven is ready to welcome you home (40280541)
174687 GREY ROAD 30, Kimberley
Type: Single Family
Land: 150.6 x 299.6 Acre|1/2 - 1.99 acres
Price: $649,900.00
A wonderful opportunity to own this one acre property with a 3 bedroom, 2 bath home that's nestled on the hillside and less than 1 km from the BVSC. This property is highlighted and adorned with a beautiful waterfall running down the escarpment where its therapeutic sound is heard all year round. The wonder of nature is captured from every window. The home features hardwood floors on the main floor with a big, bright dining room and walkout to private deck, kitchen with island, a living room where views and lights of the slopes are seen, plus 3 bedrooms and a 4 pc bath. Lower level is a walkout to front yard and driveway and offers a nice sized family room with fireplace, a big bright office, a 2 pc bath, a workshop and lots of storage. The lower level has been completely spray foamed, the propane furnace was new in 2015 and has a newer 200 amp breaker panel plus a generator panel has been wired in. A lovely 4 season home located perfectly for the outdoor enthusiasts where so many recreational attractions like skiing, Eugenia Lake, Eugenia Falls, Beaver River and the Bruce Trail are all closeby. The value of this home is not just in its walls and location, but in the possibilities it offers the next lucky owner. (38565199)
202 LAKESHORE BOULEVARD, Lake Eugenia
Type: Vacant Land
Land: 80.07 x 200.06 FT|under 1/2 acre
Price: $649,000.00
Days on the lake start here, whether it's early morning fishing, Seadoo rides with the kids, or quiet sunset cruises, this waterfront lot on Lake Eugenia is your chance to build a getaway that fits your life. Tucked near the end of a quiet dead-end street, this peaceful lot offers beautiful water views, west-facing sunsets, & direct access to all the recreation Lake Eugenia is known for. One of the few remaining vacant lots on the lake, it's the perfect setting for a well-designed cottage or modest year-round home, something that blends into the natural beauty without skimping on comfort. Launch your boat, cast a line, or simply sit dockside & let the day unfold. With minimal development left in this area, this is a rare opportunity to create something fresh in a well-loved, established community. If lakeside living is on your list, this could be exactly the place to start. (39616550)
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)
Step into The Bakery of Flesherton, where every bite is a celebration of flavour, comfort, and community! Located in the heart of charming Flesherton, this beloved bakery is a dream opportunity for anyone ready to take the reins of their own business while indulging in the art of crafting irresistible delights. From their perfectly spiced samosas that keep customers coming back for more, to donuts so soft and fluffy they practically melt in your mouth, The Bakery of Flesherton has a well-earned reputation as a local treasure. And let's not forget their lattes, a comforting hug in a cup that warms you from the inside out. These are just a few reasons this bakery has become a favourite destination for locals and visitors alike. This is more than just a bakery; it's a chance to be part of a community, spreading joy and satisfaction one delicious treat at a time. Whether you dream of perfecting your recipes, welcoming smiling faces through the door, or creating unforgettable moments over coffee and pastries, this is your opportunity to turn passion into a thriving business. Step into a space filled with warmth, character, and endless potential. At The Bakery of Flesherton, every day is an invitation to make a difference through the magic of food. Don't just bake, create an experience that will be cherished by everyone who walks through the door. Ready to take your first step toward sweet success? Let's make your bakery dreams come true, one flavourful bite at a time! (39739220)
- All Active Listings (129)
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- Town of The Blue Mountains (19)
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