Curated For You
Weatherhead Family - Ski Season Properties
High End Ski Season Properties
Curated For You
High End Ski Season Properties
chalet
4
Beds
4
Baths
8
Guests
Welcome to this stunning four-bedroom modern ski chalet, ideally situated just steps from Georgian Peaks Ski Club. Combining contemporary architecture, luxurious finishes and spectacular views of the ski hills and Georgian Bay, this exceptional property offers everything a family needs to settle in and enjoy an unforgettable winter in The Blue Mountains. Designed for the Ultimate Ski Season Imagine waking up on a snowy winter morning, enjoying breakfast overlooking the mountains and heading to Georgian Peaks for a full day on the slopes. With the ski club just steps away, your family can embrace the convenience of living close to the mountain without the long weekend commutes. After skiing, return home to the warmth of a beautiful wood-burning fireplace, gather with family and friends for après-ski, or enjoy a relaxing evening surrounded by the peaceful winter landscape. The home's impressive open-concept living area features soaring windows, heated polished concrete floors and a designer chef's kitchen with premium appliances, marble countertops and a spacious pantry. It's an ideal setting for entertaining throughout the ski season, from casual family dinners to festive gatherings with friends. Luxury, Comfort and Space for the Whole Family With four beautifully appointed bedrooms, this chalet offers generous accommodations for family and visiting guests. The luxurious primary suite features a spa-inspired ensuite and private loft, while an additional family room provides space for children and teenagers to relax after a day outdoors. A dedicated home gym, heated garage, heated driveway and walkways, and integrated smart-home technology add convenience and comfort throughout the winter months. A Winter Lifestyle Beyond the Slopes The location offers more than outstanding access to Georgian Peaks. Nearby Thornbury is a wonderful destination throughout the winter, with its inviting cafés, restaurants, boutiques and beautiful harbour. Enjoy a leisurely brunch, pick up provisions for dinner or spend an evening exploring the town after a day of skiing. The surrounding Blue Mountains also offer an extensive network of trails for winter hiking, snowshoeing and cross-country skiing. Whether exploring the Niagara Escarpment, taking a peaceful walk along Georgian Bay or enjoying the winter scenery, there is always something to do beyond the ski hills. With Blue Mountain Village and downtown Collingwood also within easy driving distance, the property offers an exceptional balance of mountain recreation, small-town charm and luxurious family living. Make Georgian Peaks Your Winter Home For families who spend their winters at Georgian Peaks, this chalet offers the opportunity to make the most of every ski day. Its thoughtful design, generous entertaining spaces and dedicated ski-storage facilities make extended winter living both comfortable and convenient.
$70,000/season
chalet
7
Beds
7
Baths
14
Guests
$50,000/season
chalet
5
Beds
4
Baths
10
Guests
$65,000/season
chalet
4
Beds
3
Baths
6
Guests
$32,000/season
house
6
Beds
5
Baths
A rare opportunity to acquire a fully custom, luxury six-bedroom retreat in one of Ontario's most coveted four-season destinations — offered for sale with pricing open to conversation based on the nature of the deal. Set just a five-minute walk from Georgian Bay and Georgian Peaks Ski Club, this stunning custom home delivers an exceptional blend of chalet warmth and modern luxury at a scale rarely available in the market. Soaring high ceilings and an open, flowing floor plan create a grand yet intimate atmosphere — the kind of space that feels equally at home hosting a large family gathering or a quiet weekend escape. Highlights for the Potential Buyer: 6 bedrooms, 5.5 bathrooms — custom built throughout Panoramic Georgian Peaks views from floor-to-ceiling windows Private hot tub — perfect after a day on the slopes or the Bay Expansive outdoor deck ideal for entertaining Gourmet kitchen with top-of-the-line appliances and finishes Finished basement with additional living space Two-car garage plus ample parking Five-minute stroll to Georgian Bay Chalet-style aesthetic with high ceilings and premium materials Strong rental history — an established income-producing asset Panoramic views of Georgian Peaks pour in through floor-to-ceiling windows, flooding every room with natural light and making the surrounding landscape an ever-present feature of daily life inside the home. The seamless connection between interior and exterior is one of this property's defining qualities. Positioned in the heart of the Blue Mountains area, this property sits at the intersection of everything that makes this region exceptional. Georgian Bay is on your doorstep, world-class skiing at Georgian Peaks is within view, and the vibrant village of Collingwood — with its restaurants, shops, and year-round events — is minutes away. Whether your vision is a full-time residence, a legacy family retreat, or a premium rental investment, this location delivers on every front. This property has been operated as a sought-after luxury vacation property through Seasonal Properties, with a proven track record of demand from discerning guests. It presents an equally compelling case as a primary residence or a legacy family chalet — properties of this scale, quality, and location do not come to market often. The current owners have priced this home at $4,800,000 and are genuinely open to discussing the right deal structure — whether that involves timing, conditions, or other arrangements that make sense for a motivated buyer. Ready to discuss? Serious inquiries are welcome. The owner is available to speak directly with prospective buyers — no layers, no delays. Reach out through the listing page or via the Seasonal Properties contact form to start the conversation. All inquiries treated with complete confidentiality. Price open to discussion based on the nature of the deal.
Price upon request
Welcome to Windrose Valley Boulevard, an exceptional luxury estate tucked into the exclusive Windrose Valley community at the base of the Niagara Escarpment. Set on approximately 2.3 private acres, this impressive home offers around 5,000 square feet of beautifully designed living space, combining the character of a mountain retreat with the scale and amenities of a true luxury residence. With six bedrooms and five bathrooms, expansive gathering spaces and remarkable proximity to the region's ski clubs, trails, golf courses and Georgian Bay, Windrose Valley Estate is ideally suited to families looking to settle into the Blue Mountains lifestyle for a month, season or extended stay. Designed for Families to Gather Step inside to an impressive open-concept interior defined by cathedral ceilings, warm wood posts, oversized windows and abundant natural light. At the heart of the home is a generous great room anchored by a gas fireplace — the perfect gathering place after a winter day on the slopes or a summer afternoon exploring the Escarpment. Multiple walkouts connect the interior with decks and balconies, while the home's spacious layout gives family and guests plenty of room to come together without sacrificing privacy. A Kitchen Made for Entertaining The expansive kitchen is designed for both everyday family living and entertaining, with a large centre island and bar seating complemented by a generous breakfast area. A separate formal dining space provides another setting for memorable dinners, holiday gatherings and evenings with friends. For families staying for several months rather than several nights, this is an important distinction: Windrose Valley Estate feels and functions like a home, allowing guests to truly settle into the region. Six Bedrooms for Family & Guests With five above-grade bedrooms plus an additional bedroom on the finished lower level, the home provides exceptional flexibility for larger families, multi-generational stays and visiting guests. Four bedrooms are located on the upper level, including a spacious primary bedroom with ensuite. A main-floor bedroom can also provide flexible accommodation or function as an office for those combining seasonal living with remote work. The additional lower-level bedroom and bathroom create further separation and privacy for guests. Your Own Private Après-Ski Retreat The finished lower level transforms the home into an exceptional year-round recreational retreat. Enjoy a spacious family and games room, private gym, sauna, wine cellar and additional living space — creating the perfect environment to unwind without leaving home. During ski season, return from the mountain for a sauna and a relaxed evening with family. During the warmer months, start the morning in the gym before heading out for golf, cycling or hiking. These are the features that make an extended stay at Windrose Valley feel truly special. 2.3 Acres Beneath the Escarpment One of the property's greatest luxuries is its setting. A long driveway leads into approximately 2.3 acres of private grounds, providing space and separation while maintaining remarkable proximity to the area's major attractions. Views toward the Niagara Escarpment reinforce the property's mountain-estate atmosphere, while decks and balconies create natural extensions of the home's living spaces throughout the warmer seasons. It is a peaceful country setting without sacrificing access to everything the Blue Mountains has to offer. Osler Bluff Ski Club is approximately five minutes away, while Blue Mountain is also approximately five minutes from the property. That means mornings can be spent on the slopes without the long drive typically associated with a country estate. Come home for lunch, enjoy the sauna after skiing, entertain friends for dinner and settle into the rhythm of an entire winter in the mountains. Despite its private setting, the property is approximately 10 minutes from historic downtown Collingwood, putting restaurants, cafés, boutiques, groceries and everyday conveniences within easy reach. Throughout the warmer months, the surrounding region opens up to golf, hiking, cycling, Georgian Bay beaches and waterfront activities. Thornbury, Blue Mountain Village and the region's private ski and golf clubs are all easily accessible, making this an outstanding base for experiencing Southern Georgian Bay throughout the year. A True Four-Season Lifestyle Property Windrose Valley Estate is ideally suited to guests seeking more than a traditional vacation rental. It is a home for families who want to live in the Blue Mountains for a season — keeping their ski equipment ready throughout winter, establishing a summer base near Georgian Bay, working remotely from the Escarpment or spending several months exploring the region before purchasing a home of their own. Whether your days revolve around skiing, golf, cycling, hiking, entertaining or simply enjoying the privacy of a beautiful country estate, this property provides the space and location to make the most of them. Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal rentals of 30+ days. Ideal for winter ski season, summer and fall stays, executive relocations and extended four-season living. Inquire today to experience Windrose Valley Estate — where 2.3 private acres, luxury amenities and exceptional access to Osler Bluff and Blue Mountain come together in one remarkable seasonal home.
Welcome to your Osler Bluff Luxury Ski Chalet, an exceptional five-bedroom seasonal retreat designed for families and friends who want to experience winter in The Blue Mountains in comfort, style, and complete relaxation. Ideally located on Grey Road 19 and just seven minutes from Osler Bluff Ski Club, this spacious chalet puts your family within easy reach of the slopes while offering something equally important at the end of the ski day: a home you'll genuinely look forward to coming back to. With five bedrooms, a two-car garage, private hot tub, sauna, golf simulator, and generous spaces for entertaining, this isn't simply a place to sleep between ski days. It's a destination in itself. Seven Minutes to Osler Bluff Ski Club - For an Osler Bluff family, location matters. Being approximately seven minutes from the club means mornings can be relaxed, first tracks are always within reach, and getting children back and forth from skiing doesn't become an event in itself. Blue Mountain Village is also approximately 12 minutes away, while Collingwood and Thornbury are both within about 15 minutes, putting dining, shopping and four-season recreation close at hand. Spend the day skiing Osler and return home to your own private après-ski retreat. Five Bedrooms Made for Family & Friends With five bedrooms, the chalet offers the space needed for an extended ski season rather than simply a weekend getaway. Families can unpack, settle in and make the property their own for the winter. There is plenty of room for children, grandparents and visiting friends, making it especially appealing for families who enjoy entertaining throughout the season. Multiple gathering spaces also mean everyone doesn't need to be doing the same thing at the same time. Adults can relax and catch up while the kids have their own space to unwind after a day outside. Your Own Private Après-Ski Club Some of the best moments of ski season happen after the final run of the day—and this property has been designed to make those moments memorable. Come home, take off the ski boots and head straight for the private hot tub. Let tired legs recover in the warmth while the snow falls around you, or retreat to the sauna for the perfect way to warm up after a cold day on the mountain. Later, turn the evening into a friendly competition in your private golf simulator. For golfers who spend the winter counting the days until the courses reopen, it's a fantastic addition. Play a round with friends, work on your swing, or organize family competitions without ever leaving the chalet. With a golf simulator, sauna and hot tub all at home, there's no shortage of entertainment when the lifts close. Built for a Real Ski Season One of the biggest differences between a great vacation property and a great seasonal home is functionality. The two-car garage is a significant advantage during a Southern Georgian Bay winter, providing protected parking as well as valuable space for skis, boots, helmets and all the equipment that comes with an active family. With five bedrooms and plenty of room to spread out, this is a home where you can establish a routine for the season—rather than feeling as though you're living out of suitcases every weekend. Wake up, make breakfast, head to Osler, come home for lunch if you choose, ski the afternoon and finish the day in the hot tub or sauna before dinner. That's what seasonal living is supposed to feel like. More Than a Winter Chalet While this property is exceptionally well suited to ski season, its location makes it equally compelling throughout the rest of the year. The Blue Mountains and Southern Georgian Bay are among Ontario's great four-season recreational destinations, with outstanding golf, cycling, hiking, mountain biking and Georgian Bay all nearby. During the warmer months, trade the ski boots for golf shoes and spend your days exploring the area's courses before returning home for an evening outside. Hiking and cycling routes stretch throughout the Niagara Escarpment, while Georgian Bay provides endless opportunities for swimming, paddling, boating and days by the water. Collingwood, Thornbury and Blue Mountain Village offer restaurants, cafés, shops and entertainment throughout the year. Your Osler Bluff Home for the Season. There is something special about having a true home base in ski country. It's having your equipment waiting in the garage rather than packing it every Friday. It's waking up after an overnight snowfall knowing Osler Bluff is only minutes away. It's friends coming back to the chalet after skiing for drinks, dinner and a round on the golf simulator. It's watching the snow fall from the hot tub before warming up in the sauna. And it's having five bedrooms so the people you want to share those experiences with can be there too. Osler Bluff Luxury Ski Chalet brings all of those elements together in one exceptional seasonal property—offering location, space, recreation and comfort just minutes from the slopes. For families looking to make The Blue Mountains home for the ski season, this is exactly the type of property that turns a great winter into an unforgettable one.
Welcome to 2 Evergreen Road, a beautifully appointed executive bungalow offering the perfect combination of privacy, space and access to the very best of Southern Georgian Bay. Set on approximately one acre of mature, park-like grounds, this exceptional 4-bedroom, 3-bathroom home provides more than 2,500 square feet of thoughtfully designed, single-level living. Located just minutes from Blue Mountain Village, skiing, golf, trails, beaches and downtown Collingwood, it is an ideal home for families seeking to settle into the region for a month, season or extended stay. Whether you're spending the winter skiing, escaping the city for summer, or simply looking for a peaceful home base near Georgian Bay, Evergreen Mountain Retreat offers a true four-season lifestyle. One of the home's greatest features is its spacious bungalow design. With the principal living spaces and all four bedrooms located on one level, the home feels open, comfortable and effortless for extended seasonal living. A garage for parking and entry to the home for ski season guests. The impressive Great Room features soaring vaulted ceilings, hardwood floors, oversized windows and a gas fireplace, creating a warm gathering place for family and friends. Ten-foot ceilings throughout much of the remainder of the home add to the sense of space, while radiant in-floor heating provides exceptional comfort during the colder months. It's equally suited to quiet family evenings after skiing and entertaining friends throughout the season. A Chef's Kitchen Made for Entertaining. At the centre of the home is a beautifully designed gourmet kitchen with stainless steel appliances, quartz and wood countertops, generous cabinetry, a bar fridge and ample preparation space. The kitchen connects naturally with the home's dining and living areas, making it ideal for everything from relaxed family breakfasts before heading to the mountain to larger dinners with friends. For guests spending several months in the Blue Mountains, this is a home that functions as a genuine residence rather than simply a place to stay. Four Bedrooms for Family & Guests. The home offers four spacious bedrooms and three bathrooms, providing excellent flexibility for families, visiting friends and extended seasonal stays. The primary suite is a private retreat with its own ensuite and direct walkout to the expansive rear deck, allowing the home's peaceful outdoor setting to become part of everyday living. One of the additional bedrooms can also function beautifully as an office or den, creating an ideal setup for professionals who want to work remotely while spending a season in the Blue Mountains. Surrounded by mature landscaping, the expansive backyard provides remarkable privacy and plenty of space to enjoy the outdoors throughout the year. It is a setting that allows you to enjoy the Blue Mountains lifestyle without sacrificing privacy or space. Perfect for the Winter Ski Season. Evergreen Mountain Retreat is exceptionally well positioned for families spending the winter in the area. Blue Mountain Village and the ski hills are only minutes away, while the region's private ski clubs — including Osler Bluff, Craigleith, Alpine and Georgian Peaks — are easily accessible.Radiant heated floors, a gas fireplace and the private outdoor hot tub make returning home after a day on the slopes almost as enjoyable as the skiing itself. You're close enough to enjoy everything happening at Blue Mountain and downtown Collingwood, yet far enough removed to return home to a quiet, private residential setting. Nearby you'll find: Blue Mountain Village and ski hills Private ski clubs Golf courses Scandinave Spa Georgian Bay beaches Hiking and cycling trails Downtown Collingwood restaurants and shops Thornbury and the wider Blue Mountains region This central location makes 2 Evergreen Road an outstanding home base for exploring Southern Georgian Bay throughout all four seasons. A True Home Away from Home Flexible Monthly & Seasonal Availability Available for monthly and extended seasonal rentals of 30+ days. Whether you're searching for a winter ski season home, a summer escape near Georgian Bay, or a peaceful extended stay close to Collingwood and Blue Mountain, Evergreen Mountain Retreat offers the space, privacy and location to make the region feel like home. Pets considered. Inquire today with Seasonal Properties to experience four-season living at 2 Evergreen Road.