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$5,350,000
4 Beds ⋅ 4 Baths ⋅ 402106 MLS
Welcome to The Highlands, Spanish Peaks’ premier ski-accessible neighborhood of luxury single-family homes. Located at 453 Outlook Trail, this beautifully appointed residence features 4 bedrooms, 3.5 baths, and expansive living spaces perfect for relaxing with family and friends after adventurous days in the mountains of Southwest Montana. The Highlands offers a rare combination of year-round outdoor access and privacy, with hiking and biking trails in the summer and ski trails running throughout the neighborhood in the winter. You'll enjoy full access to the unparalleled amenities of Spanish Peaks Mountain Club, including private ski terrain, two private golf courses, multiple pools, tennis courts, fitness centers, and world-class dining. You’ll also benefit from the five-star services and offerings of the neighboring Montage Big Sky hotel. 453 Outlook Trail showcases high-end finishes, generous gathering spaces, and seamless indoor-outdoor living, all just minutes from the best of Big Sky. Discover the unmatched lifestyle of Spanish Peaks and make this Highlands retreat your Montana home.

453 Outlook Trail, Big Sky

Courtesy of Will Littman with Berkshire Hathaway - Big Sky.
$5,800,000
5 Beds ⋅ 5 Baths ⋅ 401845 MLS
Mountain splendor and solitude with Lone Peak views! Nestled in the Fir's, sets a spectacular 5 bedroom/5 bath mountain retreat. Welcome to your dream alpine escape in the heart of Big Sky Mountain Village—where breathtaking mountain views, luxury finishes, and unmatched ski access come together to create the ultimate Montana lifestyle. This 5-bedroom, 5-bathroom residence offers over 4,400 square feet of refined living space designed for comfort, relaxation, and year-round adventure. Home is sold furnished. Perched in a prime location with ski-in/ski-out access, this home delivers sweeping views of Lone Peak and the surrounding Spanish Peaks wilderness. Soaring ceilings and expansive windows bring the outdoors in, flooding the main living areas with natural light and framing the iconic landscape. Three inviting fireplaces—one in the great room, another in the primary suite, and a third in the lower-level lounge—add warmth and ambiance throughout. The gourmet kitchen features high-end appliances, custom cabinetry, and a spacious island, perfect for hosting après-ski gatherings. Three bedrooms with en-suite bath, ensuring comfort and privacy for guests and family alike. The luxurious primary suite includes a spa-inspired bathroom, walk-in closet, and private balcony with panoramic views. Additional highlights include a 3-car heated garage, large mudroom with ski storage, dog wash and a covered outdoor patio ideal for year-round enjoyment. Whether you're seeking a full-time residence or an elite mountain getaway, this exceptional property offers the rare opportunity to own a slice of Big Sky paradise. Schedule your private showing today and experience mountain living at its finest.

11 Speaking Eagle, Big Sky

Courtesy of Michael Thomas with PureWest Real Estate Big Sky.
$9,250,000
6 Beds ⋅ 8 Baths ⋅ 400400 MLS
In the forested hills of Towering Pines, this extraordinary Big Sky retreat combines world-class architecture, refined design, and sweeping natural beauty across 20 private acres. Offering both unmatched tranquility and connection to one of the Rockies’ most exclusive private clubs, it is a legacy estate designed for generations. Ownership includes the opportunity for a coveted National Membership at Spanish Peaks Mountain Club, granting access to the Tom Weiskopf–designed championship golf course, a stunning clubhouse with fine dining, private ski lift access into Big Sky Resort, and a year-round calendar of curated events. Membership also connects owners to the broader Montage Big Sky community, elevating the lifestyle to one of true rarity at the heart of a premier resort destination. Approximately half of the residence is a newly built custom addition by OSM, strategically designed to frame sweeping views of the Spanish Peaks and Lone Mountain. Though offering remarkable privacy and serenity, the estate sits just minutes from Big Sky’s world-renowned skiing, championship golf, the Blue Ribbon waters of the Gallatin River, and the vibrant Town Center. Inside, soaring ceilings, expansive windows, and seamless indoor-outdoor transitions fill the home with natural light, while elevated finishes and clean lines create an atmosphere of timeless sophistication. Curated spaces with custom lighting evoke a gallery-like ambiance, perfectly suited for art and the discerning collector. Spanning more than 10,000 square feet, the residence balances gracious entertaining with the ease of everyday living. Six spacious bedrooms include a primary suite with dual walk-in closets, a private upstairs gym, and a lower-level office and den. A separate guest suite—complete with its own kitchen, dining nook, living room, and outdoor sitting deck—offers visitors both comfort and privacy. Additional features include an expanded three-car garage with a custom-designed mudroom, multiple living areas anchored by striking fireplaces, and a thoughtful blend of formal and casual gathering spaces. Outdoors, winding garden paths, intimate seating areas, and sweeping mountain vistas elevate the mountain living experience. Every detail reflects a commitment to craftsmanship, elegance, and enduring quality. More than a home, this is a sanctuary—an inspired retreat and a true legacy property, thoughtfully designed to be cherished for generations to come.

1200 Towering Pines, Big Sky

Courtesy of Ania Bulis with Big Sky Sotheby's.
$8,795,000
6 Beds ⋅ 6 Baths ⋅ 390301 MLS
Nestled amidst the picturesque mountain landscape awaits an extraordinary retreat. This distinguished estate presents an exquisite main house spanning approximately 9,437 SF, and a 1,404 SF guest home. Crafted in 2002, this architectural marvel showcases 12" Swedish cope logs, floor-to-ceiling windows with 30' vaulted ceilings, and panoramic mountain vistas of Ramshorn Mountain and the Gallatin Range that inspire awe within every space. Stepping inside, you're greeted by a symphony of warmth and elegance, with six fireplaces adorning the expansive living spaces, including three authentic wood-burning hearths, inviting intimate gatherings and cozy evenings alike. The gourmet kitchen, equipped with Viking, Thermador, and Bosch appliances, beckons culinary enthusiasts with its Sub-Zero wine cooler and granite countertops, while smart home technology seamlessly integrates Lutron and Crestron systems, offering ultimate control over lighting, security, and sprinklers. Year-round comfort is assured with in-floor radiant heating, a sauna, and gym area, while the outdoor kitchen and dining area provide an idyllic setting for al fresco entertaining against the backdrop of Montana's beauty. For added peace of mind, the estate boasts a backup generator, security systems, and a sprinkler system, ensuring security and tranquility in equal measure. Beyond the main residence lies a charming 1,404-square-foot guest house, built in 2010, featuring one bedroom + bonus room, one bathroom, kitchen, living room, and a spacious three-car garage with extended doors, catering to horse trailers, RVs, and more. Spread across 20 acres, the estate includes eight acres of cross-fenced land, perfect for equestrian pursuits, along with a two-stall shed and a round pen, providing ample space for cherished equine companions. Conveniently located within the prestigious Big Sky school district and a short drive from all that broader Big Sky provides- the Big Sky town center, the coveted Gallatin River, Yellowstone National Park, and the world-class skiing at Big Sky Resort are all just a short drive away. Bozeman and West Yellowstone are also just an hour away for residents to enjoy even greater access to outdoor recreation, cultural attractions, and everyday conveniences. Whether you seek a serene retreat or an entertainer's paradise, this distinguished estate promises an unparalleled opportunity to embrace with comfort the timeless allure of Montana's majestic landscape.

141 Black Wolf Ridge, Big Sky

Courtesy of Ashley Quande with Big Sky Sotheby's.

board logoIDX information provided courtesy of the Montana Regional MLS, LLC. IDX information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.