Properties Near 422 Trailside Drive Killington, VT

Live or work 2 minutes to Killington Resort's Skyeship Gondola! This unique property along the Route 4 flats is zoned mixed use for residential and/or commercial — it is currently split into 4 offices but permitting allows for up to 5 bedrooms (sleeps 10). The upstairs has a separate entrance in the back, so could be easily split into a duplex as well. So many opportunities! The flat driveway offers easy access/plowing with parking for 10. There is also a full basement for ample storage.

Exciting opportunity to own an updated 2-bedroom, 2-bathroom condominium in the highly sought-after High Ridge community! Ideally located in the coveted A Building—the closest building to the ski-home trail—this inviting mountain retreat offers the perfect blend of comfort and convenience. Inside, you'll find tasteful updates throughout, creating a warm and welcoming space that's ready to be enjoyed from day one. The living area is anchored by a wood-burning fireplace (with firewood included in the HOA fee), while large windows and two private balconies showcase views of Vermont's Green Mountains and provide the perfect setting to relax and take in the fresh mountain air. Additional highlights include in-unit laundry and sauna, a private ski locker, and the convenience of being offered fully furnished, making for a truly turnkey opportunity. Owners and guests enjoy access to the High Ridge Sports Center, featuring an indoor pool, large outdoor hot tub, sauna, and exercise equipment—ideal for unwinding after a day on the slopes, trails, or golf course. The community also offers EV charging stations, adding convenience for electric vehicle owners and guests. Whether you're seeking a year-round getaway or a mountain retreat, this well-appointed condominium is ready to be enjoyed. Call today to schedule your private showing!

Ski In Ski Out from your front door at Trailside Village on Great Eastern! Fully Renovated Exterior, commercial metal roof, siding, doors and window, stonework, decks and more! This condo offers the rare opportunity to ski and snowboard directly from your front door to the Skyeship Base, making every powder day effortless. One of only eight residences in this intimate complex, this beautifully updated one-bedroom condo combines an unbeatable slopeside location with comfort and year-round adventure. Relax after a day on the mountain in your private hot tub or sauna, cozy up by the wood-burning stove, and enjoy mountain views from the light-filled living space. Life at Killington is defined by the seasons. Winter brings legendary skiing and riding across six peaks, neighboring Pico Mountain, and the longest ski season in the East. When the snow melts, the resort transforms into a premier destination for lift-served mountain biking, championship golf, hiking, and endless outdoor recreation in the Green Mountains. The excitement continues with the highly anticipated Killington Village, creating a vibrant slopeside destination with new shops, dining, and a true ski-in, ski-out community hub. Whether you're searching for a four-season retreat, a primary residence, or an investment in one of Vermont's premier resort destinations, this is your chance to own a rare trailside property and be part of Killington's next chapter.

Charming 3-bedroom, 2-bath condo in Whiffletree featuring laminate floors throughout and a kitchen with new countertops and a stylish backsplash. Cozy up by the gas fireplace after a day on the slopes, or enjoy a quiet morning with coffee and a good book on the deck. Whiffletree amenities include a seasonal heated outdoor pool, tennis court, and playground, and the condominiums are on the shuttle route to the base area with ski-home convenience. Experience Killington’s year-round appeal: winter brings legendary skiing and riding across six peaks plus family-friendly terrain at the neighboring mountain, Pico and the longest season in the East. In spring and summer the resort becomes a premier lift-served bike park with miles of singletrack and downhill trails at your doorstep. Tee off at the championship Killington Golf Course, explore countless Green Mountain hiking trails, or savor the cool, restorative summer air. With the anticipated Killington Village development on the horizon, bringing new shops, dining, and a true ski-in/ski-out hub, this condo could be yours in one of Vermont’s most desirable resort towns.

Rare 3 Bedroom at Mountain Green- Sleeps 8"10- Top Rental Performer. True 3 bedroom units at Mountain Green are exceptionally rare" and this one is fully renovated, spacious and short-term-rental ready. Designed for large groups, it consistently outperforms studios and 1 bedroom units, especially during peak winter weekends. With an open layout and generous sleeping capacity, this unit is ideal for personal use and high-demand rentals. Three bedroom units are the highest-earning category in the complex and rarely come to market. Unit Features: 3 Bedrooms, 2 Bathrooms, Sleeps 8"10 comfortably, Open kitchen and living area, Fireplace, Private balcony with mountain views. Building Updates: Major renovations completed, including key systems, exterior improvements and infrastructure upgrades. Why 3 Bedroom Units Sell Fast: Very limited supply. Strong rental demand and revenue potential. Ideal for group stays and multi-guest bookings. Excellent balance of personal enjoyment and income. Owner has a real estate license in PA.