Montgomery, VT | 919 Highland Drive

At Jay Peak, the snow falls deeper, the air feels crisper, and time slows down just enough to remind you of why you came. Only 0.4 miles from the Stateside Ski Lift, this fully furnished 1,290sf unit with 2 bedrooms and 2 bathrooms is not just a place to stay, it is your personal retreat in the heart of Vermont’s most iconic mountain escape. Imagine waking up to the hush of fresh powder outside your window, pulling on your gear and being first in line at the lift. After a day carving lines through the East’s deepest snow, come home to a firelit evening or a cozy après-ski on the couch. Or keep the good times rolling at one of Jay Peak’s several restaurants before taking the on-call shuttle back and doing it all over again the next day. This isn’t just a retreat, it’s part of a legacy. From the retro charm of the Ice Haus skating rink to the splash and laughter echoing through the Pumphouse Waterpark, to the 18-hole golf course, and trails to explore, Jay Peak is a year-round playground. And when you're not here, let your condo work for you through Jay Peak's seamless in-house rental program. Welcome to the way winter (and every season) used to feel. Welcome to Jay Peak.

Tucked just off Route 242 on the way to Jay Peak Resort, this fully rebuilt Vermont farmhouse blends modern updates, flexible living space, and a peaceful riverside setting with over 244 feet of frontage along Hanna Clark Brook. Cross the steel bridge over the river and arrive at a home set above the brook with forest views, privacy, and easy access to year-round recreation at Jay Peak. Inside, the home has undergone a total interior rebuild with thoughtful updates throughout, including new siding, all new windows, new insulation, heat pumps providing both heating and air conditioning, and a garage expansion with cement flooring and a new garage door. High-speed internet availability also makes the property well suited for remote work or hybrid living. The kitchen is bright, functional, and designed for gathering, with generous workspace, counter seating, and an easy flow into the main living areas. Just off the living space, the front porch overlooks the brook and woods beyond. The first floor offers a spacious primary bedroom with walk-in closet and ensuite bathroom. Near the entryway, an additional room currently used as a bedroom could also work well as a guest room, office, or den. Upstairs, both bedrooms feature large closets with natural light windows, plus a full bathroom, oversized laundry room with storage and wash sink, and a spacious bonus living area ideal for a second living room, office, or reading space. Above, you’ll also find over 650 square feet of attic space with potential for future finished living space or studio space. Outside, mature landscaping, peaceful water views, and the sound of the brook create a classic Vermont setting. The large outdoor space offers excellent soil for gardening, recreation, or simply enjoying the outdoors. A move-in ready Vermont property with farmhouse character, extensive renovations, river frontage, and close proximity to Jay Peak is increasingly hard to find.

At Jay Peak, the snow falls deeper, the air feels crisper, and time slows down just enough to remind you of why you came. Tucked along White Pine Drive, this fully furnished 1,287sf unit with 2 bedrooms and 2 bathrooms isn’t just a place to stay, it’s your personal retreat in the heart of Vermont’s most iconic mountain escape. Imagine waking up to the hush of fresh powder outside your window, pulling on your gear and being first in line at the lift (just call the 24/7 on-call shuttle service to pick you up and be at the lift in 5 minutes). After a day carving lines through the East’s deepest snow, come home to a firelit evening or a cozy après-ski on the couch. Or keep the good times rolling at one of Jay Peak’s several restaurants before heading back and doing it all over again the next day. This isn’t just a retreat: it’s part of a legacy. From the retro charm of the Ice Haus skating rink to the splash and laughter echoing through the Pumphouse Waterpark, to the 18-hole golf course, and trails to explore, Jay Peak is a year-round playground. And when you're not here, let your condo work for you through Jay Peak's seamless in-house rental program. Welcome to the way winter (and every season) used to feel. Welcome to Jay Peak.

Welcome to this charming and cozy 4-bedroom, 3-bath chalet in Alpine Haven, ideally located just 3 miles from Jay Peak. Set across three levels, this spacious getaway comfortably sleeps up to 16 guests, making it an exceptional opportunity for a vacation home, family retreat, or investment property. The chalet offers the perfect combination of mountain charm, comfort, and convenience. With four bedrooms, three bathrooms, and plenty of room for guests to spread out, it is designed for memorable weekends, holidays, and year-round enjoyment.

The possibilities are endless with this historic 1885 property located in the heart of Montgomery Center! The main home features a charming 2-BR living space full of classic Vermont character and charm, making it perfect for an owner-occupied residence or vacation getaway. In addition to the main house the property also includes two, one bedroom 600 square feet accessory apartments and a 600 square foot Grandfathered commercial retail space right in the front, offering incredible income and investment potential. Located just minutes from Jay Peak Resort and surrounded by restaurants, shops, and year-round attractions, this property is perfectly situated for residential, rental, or mixed-use opportunities. Whether you are looking for a primary residence with income potential, employee housing, vacation rentals, or a unique investment property, this one deserves a serious look.