Search Grey Highlands Property Listings
109 Wodehouse Court
Grey Highlands, Ontario
Welcome to your dream home in the beautiful Beaver Valley. Nestled in the sought-after Amik subdivision, this spacious 5 bed, 3 bath, 2 car garage home offers the perfect balance of privacy, charm, and walkability. Grab a coffee from the Kimberley General Store, enjoy dinner at Hearts Tavern, and take in sunset views from Old Baldy - all within walking distance. Surrounded by mature trees, and steps away from the Bruce Trail, this home is a nature lovers paradise. The open-concept main living space is warm and inviting, with wraparound windows that bring the forest inside, and a wood-burning fireplace for cozy winter nights. Sliding doors open onto the large deck, overlooking the impressive backyard (with fire pit), and seasonal views of the escarpment. Kitchen features vaulted ceilings, stainless steel appliances, and a centre island thats perfect for gatherings with friends and family. The generous primary bedroom is located on the main floor, with direct access to the deck and a 3-piece bath. A large mudroom connects to the oversized garage, offering plenty of space for all your gear. Upstairs, you'll find three additional bedrooms and a second 3-piece bath.The lower level is built for entertaining and boasts a bright walk-out space, large rec room, propane fireplace, 5th bedroom, bathroom, and laundry. The steel roof was installed in 2019 with a 50-year transferable warranty, offering peace of mind for years to come. Families will appreciate the close proximity to two forest schools: WILDE School (K12) and Hundred Acre Wood (Pre-K8), just minutes away. Whether your'e looking to make a full-time move or simply craving more time in nature, this home delivers. Float down the Beaver River, cycle some of the best routes in Ontario, or hit the slopes at Beaver Valley Ski Club just 5 minutes away. With Thornbury, Blue Mountain, and Collingwood close by, this is a true four-season base for outdoor enthusiasts, and anyone ready to put down roots in the Valley. (id:54532)
Lt 20 Creamery Road
Grey Highlands, Ontario
Welcome to this scenic large buildable lot in the charming village of Kimberley, Ontario a rare opportunity to create your custom home in one of the most picturesque regions of Grey County. Set against the stunning backdrop of the Niagara Escarpment, this property offers breathtaking views and endless possibilities. Located just 35 minutes from Collingwood and only 15 minutes from The Roost Winery, you'll be surrounded by local charm, nature, and year-round adventure. Kimberley is home to vibrant shops, cozy restaurants, and some of Ontarios best hiking trails, including access to the Bruce Trail / Beaver Valley Trailer just minutes away. Imagine sipping coffee on your future deck while watching the sun rise over the ski hills. With nature at your doorstep and all-season activities nearby, this lot is the perfect canvas for your weekend retreat or full-time home. As an added bonus, the seller is a custom builder and is available upon request to help you design and build your dream home, tailored to your vision and lifestyle. (id:54532)
554014 Road 55
Grey Highlands, Ontario
Are you looking for a property where you can keep a few animals, grow your own food, and still enjoy your morning coffee with a view? This 10-acre spot might be exactly what you've been hoping to find. With a great balance of hayfield, pasture, and a bit of bush, it's a setup that works whether you've got horses, goats, chickens, or just want some space to breathe. The house is a 2+1 bedroom bungalow that feels easy to settle into. The main floor is open-concept and freshly updated, with a beautiful stone-countertop kitchen and a modern three-piece bath. Downstairs, there's a partially finished rec room, laundry, and a third bedroom (just note the window doesn't meet egress and a second window has been covered ), plus a propane fireplace that keeps things warm all winter. There's also a handy walk-up from the side for easy in-and-out. The land itself is where this property shines. There's a small barn, a drive shed, roughly 4.5 acres of hayfield, 2 acres of pasture, and a 1-acre bush with a trail for walking or riding. And if you've been boarding your horses, this is your chance to finally bring them home, with almost everything you need already in place. Whether you're feeding animals, hauling hay, or just watching the seasons change, the layout here just makes sense. And when the work's done? Head up the hill to one of the most charming little spots on the property, a campfire area with a "tiki" bar and hydro. It's the perfect weekend getaway without ever leaving home. Nicely landscaped, in a great location with two road frontages, this is the kind of property that lets you live the hobby farm life without feeling overwhelmed. (id:54532)
Pt Lt 170 Con 2 Road 170
Grey Highlands, Ontario
3 Acres in Grey Highlands! Nestled amidst the breathtaking beauty of nature, this 3.03-acre parcel of vacant land offers you the opportunity to create your own private sanctuary. Grey Highlands offers a picturesque landscape, surrounded by the serene beauty of waterfalls, the Bruce Trail, the Osprey Bluffs, and the Saugeen and Beaver Rivers in the area. Conveniently located just a 5-minute drive from the charming town of Flesherton, you'll enjoy easy access to local amenities, including shops, restaurants, and schools. Plus, with Collingwood and Owen Sound a mere 45-minute drive away, you'll have the best of both worlds the peaceful seclusion of rural living and the vibrant energy of nearby urban centres. Envision yourself surrounded by nature's splendor or creating a tranquil retreat away from the hustle and bustle of city life, this property offers wonderful possibilities. Don't miss out on the chance to make your dreams a reality seize this opportunity to own a piece of Grey Highlands paradise today! Buyers can look into the possibility of building on this parcel with the Municipality. (id:54532)
B - 39 Main St Street E
Grey Highlands, Ontario
Charming and Spacious 1-Bedroom Apartment with Private Entrance. This bright and spacious one-bedroom apartment is located on the second floor and features its own private entrance, offering both comfort and privacy. Thoughtfully updated throughout, the interior combines modern finishes with a traditional layout perfect for those who prefer clearly defined living spaces. The apartment includes a separate living room, a full kitchen with updated cabinetry and appliances, and a well-proportioned bedroom with closet. The freshly renovated interior features neutral tones, updated flooring, and plenty of natural light throughout. Ideal for a single professional or couple, this well-maintained unit is move-in ready. Located in a quiet, convenient neighbourhood, its just minutes from shops, restaurants, and transit. Enjoy the charm of a classic layout with the comfort of modern updates in this lovely upper-level rental. (id:54532)
27-29 Main Street E
Grey Highlands, Ontario
Built in 1875, this home is filled with the timeless charm of its historic roots. Step inside and you're welcomed by an inviting foyer that hints at the character waiting within. To your right, the sunlit dining room feels instantly comfortingideal for family meals or hosting friends. Original hardwood floors, soaring ceilings, and detailed moldings carry the warmth of the past into every room. The spacious living room is full of potential, whether you're curling up with a book or entertaining a crowd. Built-in bookshelves create a cozy nook for reading or showcasing cherished keepsakes. The kitchen blends old-world charm with modern convenience, offering space for casual dining around an eat-in table, and a traditional woodstove that brings rustic comfort and winter warmth. This updated kitchen is a dream for anyone who loves to cook. A four-piece bath and laundry on the main level add everyday ease. Just off the kitchen, a flexible roomonce an officecould become a sun-drenched studio, den, or quiet retreat, thanks to its south-facing windows and views of the backyard. Step outside to a peaceful patio overlooking a lovingly maintained garden with flowering trees, perennials, and your own veggie patch. The charm continues upstairs with a second full bath, and four large bedrooms. The property also includes 27 Main St E., a separate detached building with its own entrance. Formerly a doctors office, bakery, and bookkeeping service, it's ideal for a home-based business, in-law suite, or income-generating rental. Perfectly located just steps from Markdales main intersection, youre within walking distance to the new hospital, school, and all downtown conveniences. (id:54532)
408082 Grey 4 Road
Grey Highlands, Ontario
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. (id:54532)
814222 Greenery Lane
Grey Highlands, Ontario
Welcome to your private retreat just outside of Flesherton, Ontario, a beautifully updated 5-bedroom, 3-bathroom home nestled on 6.6 acres of peaceful countryside. Surrounded by mature trees and scenic views, this property offers the perfect blend of modern comfort and natural beauty.Currently operating as a successful Airbnb, this home presents an incredible opportunity for those seeking investment potential or a turn-key short-term rental. The spacious layout and desirable location make it a favourite among guests year-round.Inside, you'll find a fully renovated kitchen with stylish finishes, perfect for hosting and everyday living. The updated lower-level bathroom, combined with the flexible floor plan, offers comfort and functionality for families, groups, or multi-generational living.Step outside and unwind in the hot tub or sauna, enjoy the tranquil setting around your spring-fed pond, or explore the expansive 6.6-acre lot surrounded by nature.Ideally situated just minutes from Hoggs Falls, Lake Eugenia, and Beaver Valley Ski Club, this home is a nature lovers paradise with four-season activities just down the road.Whether you're looking for a full-time residence, a getaway, or a proven income-generating property,this one checks every box. (id:54532)
262 Canrobert Street
Grey Highlands, Ontario
Cute cottage on a treed lot in Eugenia. Excellent location on a dead end road but only steps to public beach and boat launch. Bruce trail, ATV trails, grocery/LCBO store are all close by. Partial lakeview from deck and sunporch/dining area. Living room features a propane fireplace for those cool evenings. 2 garden sheds to store your tools and beach toys. Cottage will be sold turn key with just personal items excluded. Has been a popular short term rental and could be continued. Get ready to enjoy the summer at the Lake. (id:54532)
47014 Old Mail Road
Grey Highlands, Ontario
Location and privacy are all in one. Only 12 minutes to Thornbury or Georgian Peaks Ski Club set on 20 breathtaking acres along storied Old Mail Road in Grey Highlands, this extraordinary estate is a rare convergence of heritage, design, and natural beauty. Anchoring the property is a distinguished main residence dating to 1863 rich with history and perched above a natural grotto carved into escarpment stone, offering a poetic reminder of the lands ancient character. The home is a rare blend of heritage charm and modern refinement. Painstakingly maintained and thoughtfully updated, it offers contemporary conveniences while preserving the craftsmanship and character that make it truly unique. The main floor features two powder rooms, one with a private sauna, and a glass-wrapped sun/family room with panoramic views and walkout to a full-width back deck. A gracious living room with a wood-burning fireplace anchors the home, while a separate dining room offers space for intimate meals or larger gatherings, enhanced by original built-ins that span the far wall. Upstairs, three bedrooms and two full baths include a spacious primary suite with four-piece ensuite. Original architectural details throughout speak to the homes storied past. A thoughtfully designed guest house, by architect Anthony Belcher, offers modern living in harmony with the surroundings. A private tennis court sits quietly among the trees. The pool area, also designed by architect Anthony Belcher, is a masterclass in landscape integration set on a sheltered terrace above a tranquil pond with all-day sun, panoramic Beaver Valley views, and a steel/Ipe pergola for light shade. A stone wall shields the space, acting as a retaining wall and heat sink, while a cabana with 2-piece bath, bar sink, and fridge offers deep-set porches. A curved stone garden wall reflects warmth and supports lush plantings. This is a rare opportunity where privacy, views, history, and thoughtful design converge in lasting harmony. (id:54532)
429571 8th Concession B Concession
Grey Highlands, Ontario
Private 2 Acre lot on a well maintained country road just 3 Km from Singhampton and 20km from Collingwood/Blue Mountains. Elevated building envelope is partially cleared. Rough driveway is installed. Clean spring-fed pond(M R Ducks, only some will get this). 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, ski hills of Devils Glen, Beaver Valley Ski Club, Blue Mountain. Fresh air and clean living, greener pastures do exist! Are you a reputable builder? Ask about incentives available. (id:54532)
Lt 29&30 Devaition Rd Road
Grey Highlands, Ontario
Beautiful 98.6 acre property, roughly 40 ac workable, mature hardwood bush and some reforested white pine. (id:54532)
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Sotheby's International Realty Canada,
Brokerage
243 Hurontario St,
Collingwood, ON L9Y 2M1
Office: 705 416 1499
Rioux Baker Davies Team Contacts

Sherry Rioux Team Lead

Emma Baker Team Lead

Craig Davies Team Lead

Jacki Binnie Sales Representative

Hollie Knight Sales Representative

Manar Vandervecht Real Estate Broker

Michael Maish Sales Representative

Almira Haupt Finance Administrator
Google Reviews






Emma, thank you for your professionalism, your grit, your reliability, your wisdom, and your laughter! It made a world of a difference.
Congratulations as well to Holly. Well done, Holly!!!
With gratitude,
Silke and Family

I have had my fair share of experience with Realtors as a custom home builder and past home purchases. Sadly, most of my experiences have not been great, feeling like just another self serving number in the Rolodex.
When it came time to buy our family's dream home, we didn't envy anyone taking on the task. My husband and I had very different checklists and a niche search for the area, and the expectations were extremely high. In addition, I was 4 months postpartum, and we were back and forth from Oakville to Muskoka without planted roots. Imagine...
Sherry spent TWO years touring us around homes. We made two offers on two different homes that were both negotiated and accepted on our terms, based on Sherry's extreme ability
to negotiate, but upon inspections, we decided to walk away with nothing but extreme support from Sherry and her team.
Two + years in the making, and at minimum 150+ hours of Sherry's time spent, we decided to go and see the dream home that was WELL out of our price range. Sherry encouraged us to take the slight chance that we could negotiate the purchase if we fell in love. Well, we fell in love, and after a lot of back and forth, Sherry called to tell us that she had gotten the deal done. (insert tears).
The level of care, guidance, due diligence, marriage counseling, life coaching, and, above all, knowledge was nothing short of amazing.
Sherry has become our forever Agent and a friend. Thank you Sherry and the entire team. Thank you. Thank you.





Thank you Craig!

I would highly recommend Sherry, she is a joy!







Would highly recommend

We look forward to working with Jacki for many years to come.



We spent some time visiting different homes and we never felt any pressure to buy.
Once we found our place Sherri and her colleague Craig were so helpful guiding us through the purchase process.
I would highly recommend working with Sherri and her team.




Selling a beloved property can be daunting, but with Sherry in charge, worries melted away. My husband and I have no hesitation recommending Sherry as a listing agent.








Honestly, she's the best real estate agent I have ever had!







Alex Cunningham.


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