Storybook woodlands, majestic views and an unmatched location
OUTLAW REALTY
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There are few places in the American West that still feel undiscovered. Not because they’re unknown, but because they remain protected from time, crowds and compromise. Big Sky is one of those places, and one of its rarest properties is now for sale.
High above Big Sky is a 20-acre peninsula of land with sweeping views in three directions, nestled in the ultra-private, unspoiled community of Lost Trails. Accessed by a little-known mountain road halfway between the Meadow Village and the mountain, the area has buried electric and is just minutes from high-speed chairlifts in one direction and Blue Moon’s cheese bagels in the other. This is the trifecta of real estate’s “location, location, location” principle.


If that wasn’t enough, Lost Trails owners have direct (and gratis) access to Lone Mountain Ranch’s famous Boomerang Trail that winds through most of the parcels and connects to a world-class 80-kilometer cross country trail system. In a master-planned community of only eight 20-acre properties, 121 Old Toby Road is a spectacular standout.
A softly illuminated driveway lined with wooden lamp posts curves through the pines, revealing epic views of Yellow Mountain and Wilson Peak. Turning the corner to the house, Lone Mountain’s dramatic landscape looms large, anchoring the west end of an astonishing view panorama that includes Buck Ridge, the Yellowstone Club, Spanish Peaks and down the valley to the Meadow Village. Sweeping lawns, rock gardens and storybook woods, meticulously groomed for more than two decades by the owners who built the house, surround two structures.
Perched atop a charming natural knoll with epic views in two directions is the masterfully crafted, 2,000 square foot home originally intended to be an oversized guest house. It overlooks a spacious garage and guest apartment that itself has breathtaking views of Lone Mountain from a high balcony. Both places are rich in master craftsmanship and whimsical details, including a glass floor in the cupola, reclaimed wood throughout and wide-plank, Douglas fir floors and a hand-crimped copper roof. A soaring fireplace in the living room was built by the same stonemasons who had just completed Bill Gates’ first home in the Yellowstone Club.
A large, landscaped meadow frames the site of a potential future main house that will connect to the garage, all ready to go with septic and utility conduits. Two stone patios create places and spaces to revel in the majesty of Montana to the west and south.

“We decided to buy this property within five minutes of stepping onto the land,” says Steve Barry, an outdoorsman who has climbed two of the world’s highest peaks and hunted all over the world.
Barry’s wife, Carey O’Donnell, taught skiing on the Italian side of Mont Blanc and built a successful media career that got its start in the North American ski industry. Both know and love the mountains and have created pure magic from the natural beauty of their property. Carey spent four years improving existing game trails into remarkable hiking paths throughout the property, adding log stairways to help with the steepest sections. Steve has thinned the woods, disappeared fallen logs and trimmed low branches over at least 12 of the 20 acres, allowing grasses to grow and creating woodlands that set the local standard for both fire safety and aesthetics.
The local elk herd appreciates that most of all.
Carey O’Donnell is the listing agent for this extraordinary property and knows very well how rare it is to find 20 acres with a home that personifies the luxury Montana aesthetic so close to everything Big Sky offers. To learn more about 121 Old Toby Road or to set up a viewing, call or email her at carey@odonnell.agency or 561-762-7166.




