Grey Highlands Real Estate

Grey Highlands Real Estate

Welcome to Grey Highlands, a picturesque gem nestled in the heart of Ontario, Canada. This charming municipality is renowned for its stunning landscapes, outdoor adventures, and vibrant community spirit. With rolling hills, lush forests, and pristine rivers, Grey Highlands offers a serene escape from the hustle and bustle of urban life, making it an ideal destination for nature lovers and those seeking a quiet retreat.

The area is rich in history and culture, with a blend of quaint villages and modern amenities. Explore the charming town of Flesherton, known for its historic buildings and warm hospitality, or visit Markdale, where you can enjoy local shops and delightful eateries. Grey Highlands is also home to the scenic Beaver Valley, a haven for outdoor enthusiasts, offering hiking trails, skiing, and snowboarding in the winter months.

For those who appreciate the arts, the region hosts various festivals and events throughout the year, showcasing local talent and celebrating the community's diverse heritage. The friendly residents contribute to a welcoming atmosphere, making it easy to feel at home in this tight-knit community.

In addition to its natural beauty and cultural richness, Grey Highlands boasts a strong real estate market, with a range of properties from cozy cottages to expansive country homes. Whether you’re looking to invest in a vacation getaway or settle down in a peaceful environment, Grey Highlands presents endless possibilities. Discover the charm of Grey Highlands today, where every season brings new adventures and a sense of belonging.

Newest Listings in Grey Highlands

155 Canrobert Street, Grey Highlands
$825,000
3 Beds ⋅ 3 Baths ⋅ X14088870 MLS® #
What if home changed the way you spent your Saturdays? Slower mornings, time to explore, and a place you look forward to coming home to. Welcome to a fresh start in Eugenia. Newly constructed in 2026 and never lived in, this 3-bedroom, 2.5-bathroom home is ready for its first chapter-and yours. Picture your morning routine taking shape, your favourite chair finding its spot, and friends gathering for the first of many evenings together. There's something special about making a home your own from the very beginning. Beyond your door, discover the lifestyle that makes Eugenia so appealing. Spend your days exploring local trails, taking in Eugenia Falls, or enjoying time by Lake Eugenia. Follow a little adventure with an evening at home, settling into the spaces and routines that become your everyday life. Whether you're putting down roots or beginning something new, this is an opportunity to create a home filled with your own memories. Come imagine your first Saturday here. (id:5764)

155 Canrobert Street, Grey Highlands

Listing courtesy of Real Broker Ontario Ltd..

529802 Osprey The Blue Mountains Townline, Grey Highlands
$1,849,000
5 Beds ⋅ 3 Baths ⋅ X14088606 MLS® #
Discover an extraordinary four-season retreat nestled on 32 acres of breathtaking Niagara Escarpment landscape, where ultimate privacy, sweeping views and endless outdoor adventure come together. A true playground for nature lovers, this remarkable property features private trails, natural caves and rugged escarpment terrain, offering exceptional opportunities for hiking, mountain biking, cross-country skiing, snowshoeing and ATV adventures right outside your door. From vibrant autumn colours to snow-covered winter wonderlands, every season brings something spectacular.Thoughtfully and extensively renovated, the residence blends refined modern finishes with warm, inviting chalet character. Vaulted ceilings, expansive windows and beautifully curated living spaces frame the spectacular natural surroundings, while a stunning floor-to-ceiling stone feature with a high-end wood-burning fireplace creates a welcoming focal point. The beautifully updated kitchen, open-concept living and dining areas, and seamless connection to the outdoors make this home equally suited to quiet escapes and memorable gatherings.With two bedrooms on the main level and three additional bedrooms in the fully finished walkout lower level, there is ample room to host family and friends. Outdoors, a stunning pool surrounded by gorgeous hardscaping creates a private resort-like setting, perfect for summer afternoons and entertaining beneath the escarpment backdrop. A detached double garage provides excellent space for recreational equipment, outdoor toys or a workshop. Updated water and well systems in 2026 add further peace of mind.Whether you're seeking an exceptional full-time residence, a private country escape or the ultimate four-season adventure property, this rare 32-acre offering delivers an extraordinary combination of natural beauty, modern comfort and complete seclusion. Your own private piece of the Escarpment, where every season is an invitation to explore. (id:5764)

529802 Osprey The Blue Mountains Townline, Grey Highlands

Listing courtesy of Royal LePage Signature Realty.

185 Raglan Street, Grey Highlands
$1,025,000
5 Beds ⋅ 3 Baths ⋅ X14088390 MLS® #
Tucked away at the end of a quiet cul-de-sac in the charming community of Eugenia, this beautifully crafted 2025-built bungalow offers the perfect blend of modern comfort, thoughtful design, and small-town living. Featuring 5 bedrooms and 3 bathrooms, this home offers plenty of space to grow, gather, and make lasting memories. Step inside to discover a bright, inviting living room with vaulted ceilings that create an airy, open feel. Custom cabinetry throughout the home adds both character and functionality, reflecting the attention to detail found in every corner. The fully finished basement extends the living space, offering endless possibilities for family movie nights, entertaining guests, or creating a space of your own. A generously sized storage room ensures there's a place for everything. Outside, the fully fenced backyard provides a private space for children, pets, and summer evenings spent outdoors, while a convenient storage shed keeps all your seasonal extras neatly tucked away. Beyond your doorstep, enjoy everything that makes Eugenia such a special place to call home. From the natural beauty of Eugenia Falls to days spent at Lake Eugenia and exploring the surrounding trails, outdoor adventure is never far away. New construction, a peaceful setting, and a lifestyle that embraces the best of Grey Highlands. Welcome home to Eugenia. (id:5764)

185 Raglan Street, Grey Highlands

Listing courtesy of Real Broker Ontario Ltd..

125 Kimberley Court, Grey Highlands
$725,000
5 Beds ⋅ 5 Baths ⋅ X14081080 MLS® #
Welcome to 125 Kimberley Court, a spacious five-bedroom, five-bathroom chalet tucked away on a private lot in the desirable AMIK subdivision, just outside the village of Kimberley. Ideally suited to Beaver Valley Ski Club members, this is a wonderful four-season retreat with plenty of room for family and friends. The thoughtfully designed chalet offers generous living space for entertaining after a day on the slopes, with five bedrooms and five bathrooms providing comfort and privacy for larger families or two families sharing a mountain getaway. A 600-square-foot deck extends the living space outdoors, creating a wonderful setting for summer evenings, après-ski gatherings and relaxed weekends in the Beaver Valley. The private cul-de-sac setting offers a peaceful backdrop while still being close to everything that makes this area so special. The charming village of Kimberley is just minutes away, with Hart's restaurant, the village store and the new Kimberley Café, while Beaver Valley Ski Club and the surrounding trails, hiking, cycling and other four-season activities are close at hand. Whether you're looking for a dedicated ski chalet, a four-season family retreat or a property that can accommodate two families, 125 Kimberly Court offers flexibility and plenty of opportunity. The property also has an established rental history, adding another dimension to its appeal. Come enjoy the Beaver Valley lifestyle - where weekends naturally turn into long weekends and every season brings something new to explore. (id:5764)

125 Kimberley Court, Grey Highlands

Listing courtesy of Chestnut Park Real Estate.

23 Argyle Street, Grey Highlands
$600,000
X13882112 MLS® #
117'x82.5' site in the downtown core of Markdale. Municipally owned land behind the lot and facing the former Markdale hospital this location is ideal for future development opportunities. C1 zoning permits multiple uses including: Professional and business offices, Retail commercial, Restaurants, Single detached and multi-attached residential uses, Light industrial uses, and more. Being sold for land value, building is not habitable. (id:5764)

23 Argyle Street, Grey Highlands

Listing courtesy of Royal LePage RCR Realty.

320047 170 Road, Grey Highlands
$699,000
3 Beds ⋅ 2 Baths ⋅ X13881764 MLS® #
Set on 3 acres in Grey Highlands, this property offers a 3 bed, 2 bath bungalow, a 30'x40' workshop, a barn with a chicken coop, and a spring-fed pond. With two separate living spaces, the layout provides seamless potential for income opportunities or multi-generational living. The main living space welcomes you into a bright living room with a cozy wood stove. The layout features two good-sized bedrooms, a bathroom, and a functional kitchen and dining room. The dining room has a walkout directly onto the back deck for seamless outdoor entertaining. Adding to the layout's adaptability, there is a 2nd living space, with it's own separate entrance. This space features its own kitchen, bathroom, and a flexible bedroom and living area. Situated on a quiet road minutes from Flesherton and Dundalk, this location combines country views with easy access to highways, local dining, outdoor recreation, and regional hubs like Owen Sound & Shelburne. (id:5764)

320047 170 Road, Grey Highlands

Listing courtesy of Royal LePage RCR Realty.

585216 Sideroad 10A, Grey Highlands
$1,195,000
3 Beds ⋅ 1 Baths ⋅ X13877170 MLS® #
Escape the ordinary and discover 25 private acres where country living, recreation and possibility come together. Just a few hundred metres from Grey Rd 12 on a quiet dead-end road, this diverse property offers privacy, open space and room to breathe. At its heart is a warm, inviting 3-bedroom bungalow with easy one-level living. The open-concept interior features new vinyl flooring, a sunroom and a cook's dream kitchen with abundant cabinetry and counter space. A wood-burning stove adds warmth and ambiance, while a heat pump provides heating and A/C. The home opens onto a beautiful back deck with outdoor cooking and bar areas plus a hot tub, overlooking nearly an acre of fenced and gated lawn with mature trees - an incredible outdoor living space. A fully insulated 20' x 30' three-bay garage compliments the impressive 25.5' x 60.5' shop. One side is a woodworking shop while the second is a clean, insulated space ideal for a home business, studio or hobbies. The building also contains an attached chicken coop. The 48' x 48' barn is a true showpiece, transformed with a new concrete floor, custom bar and beautiful new lighting into an exceptional entertainment space that will be the envy of your guests. Beyond the barn, a separate elevated 16' x 32' deck is tucked privately into the property to further enjoy the peace and quiet found at this stunning property. Just 8 minutes to Markdale, approx. 30 minutes to Blue Mountain/Collingwood, 24 minutes to Meaford/Thornbury and 30 minutes to Owen Sound - skiing, Georgian Bay, dining, shopping and four-season adventure are within easy reach. (id:5764)

585216 Sideroad 10A, Grey Highlands

Listing courtesy of Royal LePage RCR Realty.

123 Lakeview Road, Grey Highlands
$1,699,900
5 Beds ⋅ 3 Baths ⋅ X13876836 MLS® #
Brewster's Lake - over 200' waterfront with a bungalow, shop and garage on a 3.2 acre hardwood lot. Lake views from nearly every room in the home. Spacious rooms throughout the 2,500 square foot main level including open concept kitchen, dining and living areas with vaulted ceilings and a wood-burning fireplace. The walkout basement is fully finished with massive family room, office or 5th bedroom with ensuite; walkout to hot tub, patio and lakeside. SHOP 30x52 with in-floor heat, spray foam insulation, Trusscore interior, 3 roll up doors; detached single garage and attached double garage with in-floor heat. On demand hot water, generator back up, metal roof, new windows (2018), central air, water system, greenhouse, hot tub and more. The private waterfront boasts a sandy beach, dock and firepit. Four season living in a four season playground 20 minutes to Collingwood and Blue Mountain, 10 minutes to Devils Glen Country Club (private) and minutes away from year-round trails and recreational activities. Includes part ownership of additional waterfront lot. (id:5764)

123 Lakeview Road, Grey Highlands

Listing courtesy of Royal LePage RCR Realty.

573042 Side Road 57A, Grey Highlands
$999,000
5 Beds ⋅ 2 Baths ⋅ X13871924 MLS® #
Escape to 20+ acres of your own private playground in the heart of Grey Highlands, where four-season adventure begins right outside your door. Tucked away at the end of a quiet country lane and surrounded by mature woods, this property offers exceptional privacy and a connection to nature that is increasingly hard to find. Explore acres of signed trails through the woods, tap your own maple trees for syrup, or spend summer days kayaking and paddle boarding across the large spring-fed pond and through the surrounding wetlands. When winter arrives, lace up your skates and enjoy the pond under the lights, head out snowmobiling or snowshoeing, or hit the slopes at Devil's Glen Country Club, approximately 20 minutes away. A waterfall feature, abundant wildlife, incredible stargazing and multiple fire pit areas make the property just as inviting when you're staying close to home-you can even camp in your own backyard.The bright, open-concept home is made for gathering, offering 5 bedrooms, 2 bathrooms, hardwood floors, a main-floor primary bedroom, wood stove and multiple living and entertaining spaces. Recent improvements include new appliances, updated laundry/mudroom with custom cabinetry, refreshed lighting and paint, a new water pump and pressure tank, and an updated living room entertainment wall with fireplace. Two detached garages offer exceptional space for vehicles, recreational equipment and hobbies, with electricity to both, loft storage and an insulated, heated wood shop. Additional features include powered bunkies and a generator panel with manual transfer switch. All this while remaining approximately 20 minutes to Devil's Glen, 30 minutes to Shelburne and 35 minutes to Collingwood. A full-time country home or four-season escape designed for muddy boots, starry nights, fires with friends and weekends that feel like a getaway-without ever leaving home. (id:5764)

573042 Side Road 57A, Grey Highlands

Listing courtesy of Royal LePage Signature Realty.

104 Butternut Court, Grey Highlands
$1,295,000
5 Beds ⋅ 4 Baths ⋅ X13870348 MLS® #
Never lived in and custom built, 104 Butternut Court is one of just twelve residences tucked into Beaver Valley Woodlands, a private cul-de-sac enclave in one of Grey County's most sought-after four-season destinations. Set on 1.37 private acres, ownership also includes exclusive use of 16 acres of private conservation land shared among the twelve residences. Inside, approximately 3,500 sq. ft. of finished living space spans three levels with five bedrooms and four bathrooms. Soaring vaulted ceilings bring drama to the main living space, while a sculptural glass-and-steel staircase becomes a work of art in its own right. White oak hardwood, oversized windows, a reclaimed wood mantel and wood-burning fireplace add warmth to the clean architectural lines, while natural stone grounds the contemporary exterior. Superior quality extends beyond the finishes, with upgraded insulation throughout the entire home and soundproofing in all interior walls and floors. The finished lower level features heated polished concrete floors, a gym/flex room, two additional bedrooms and a large recreation area. The 19' x 19' covered porch extends the living space into the private, mature surroundings, equally suited to summer mornings and evenings after a day on the slopes. The oversized heated garage features epoxy floors and plenty of room for four-season gear. CAT5 wiring to every bedroom and the office adds convenience for remote work, streaming and gaming. Beaver Valley Ski Club is less than five minutes away, while Markdale and Flesherton keep everyday amenities close. From skiing and hiking to cycling, golf, Georgian Bay and the Blue Mountains, this is a move-in ready home built for the way people come here to live. Brand new and waiting for you, 104 Butternut Court could be your next move. (id:5764)

104 Butternut Court, Grey Highlands

Listing courtesy of Royal LePage Exchange Realty Co..

446070 Johnston's Sideroad, Grey Highlands
$1,250,000
3 Beds ⋅ 3 Baths ⋅ X13862708 MLS® #
Tucked away at the end of a quiet dead-end road, this extraordinary 5.89-acre property offers a level of privacy and natural beauty that is rarely found. With direct access to the Bruce Trail from the edge of the property, it is a true hiker's paradise. Bordering Ontario Land Trust lands and showcasing breathtaking valley views, the setting is nothing short of spectacular - perfect for hiking, scenic cycling, or simply immersing yourself in nature. Unwind on the flagstone patio and take in the peaceful, panoramic surroundings. Ideally located just 7 minutes to the top of Beaver Valley Ski Club and 10 minutes to the shops and restaurants of Markdale and Flesherton, this property offers the perfect balance of seclusion and convenience, ideal for full-time living or a four-season recreational retreat. The grounds are well-suited for hobby farming or equestrian use, featuring a 20' x 15' drive shed, two-stall barn, and 1-acre paddock. The home offers 3 bedrooms and 2.5 bathrooms, with two bathrooms beautifully renovated with Caesarstone counters and oak vanities. The kitchen features granite countertops, while maple flooring adds warmth throughout the main living spaces. A spacious basement provides excellent flexibility, with the potential to add two additional bedrooms while still maintaining ample storage and living space. The home is equipped with an efficient geothermal forced air system for heating and cooling, a VanEE air exchange system, and a Swordfish UV light integrated into the furnace. A truly rare opportunity to own a private countryside escape in one of the area's most unique and sought-after settings. (id:5764)

446070 Johnston's Sideroad, Grey Highlands

Listing courtesy of Royal LePage Locations North.

194247 Grey Road 13, Grey Highlands
$249,900
X13860780 MLS® #
Vacant Lot in Eugenia! Discover the opportunity to own a 1.5-acre building lot in the quaint and picturesque community of Eugenia. Nicely cleared and level, this property is framed by mature trees, offering a peaceful setting and a wonderful canvas for your future home. Situated along Grey Road 13 (Beaver Valley Road), this scenic location puts you close to all that Grey Highlands has to offer. Outdoor enthusiasts will love the easy access to year-round recreation, including skiing, hiking, cycling and rock climbing, while those seeking a quieter lifestyle will appreciate the natural beauty and relaxed atmosphere of the area. Eugenia Lake is just a short walk or drive away, featuring a public beach and boat launch for swimming, boating and enjoying summer days by the water. Nearby Eugenia Falls offers another beautiful destination to explore, with a fascinating connection to the area's historic Gold Rush. Whether you're looking to build a year-round home or create your own peaceful retreat, this property offers space, scenery and an exceptional location in the heart of Grey Highlands. Please do not walk the property without your REALTOR. (id:5764)

194247 Grey Road 13, Grey Highlands

Listing courtesy of .

Start Your Search