300 Trailside Drive D, Killington, VT 05751

• 3 beds |
• 3 baths

Property Description

True Ski-on/Ski-off! Wake up where the mountain meets your back door. Your new Vermont retreat sits directly alongside the Great Eastern Trail, offering front-row access to Killington’s legendary terrain and an easy glide down to the Skyeship Base on Route 4 and the Skyeship Gondola. The trail is so close you can watch skiers and riders pass by as you sink into the hot tub. This three-bedroom, three-bath single-family home has recently been transformed with a comprehensive exterior renovation, showcasing new exterior insulation and finishing system (EIFS), authentic Vermont fieldstone, recently updated decking, standing seam roof, doors, windows and entryway. A large open driveway allows for ample parking. As part of the Trailside Village Association, the home delivers an unmatched lifestyle for ski and ride enthusiasts. Pop in for lunch, warm up by the fire, take a quick soak, then step right back onto the trail, no shuttles, no parking, no hassle. Beyond personal enjoyment, the property has a proven track record as a highly successful, four-season rental, making it an attractive investment opportunity. Whether you’re looking for a mountain retreat, an income-producing property, or both, this home offers it all. In the summer month enjoy the sounds of the stream crossing the trail just above the house, creating a waterfall amplifying the calming nature of the outdoors as the water flows between the rocks. This is Killington living at its finest! Schedule your private showing and make the mountain yours.

Listing Status:

Active

Date Added:

February 11, 2026

Data Last Updated:

April 5, 2026 at 6:58PM

Listing Office:

Elevations Team - Real Broker LLC : 610-574-6973

Listing Agent:

Nathan Mastroeni : 610-574-6973 : Nathan@ElevationsVT.com

MLS ID:

5076313

Interior

• General: Cathedral CeilingDining AreaFireplace Screens/Equip1 FireplaceFurnishedHot TubKitchen/DiningNatural LightSaunaBasement Laundry
• Appliances: DishwasherDryerMicrowaveRefrigeratorWasherGas StoveOn Demand Water Heater
• Basement: Walkout
• Flooring: CarpetWood
• A/C: Mini Split
• Heating: PropaneBaseboardHeat Pump

Exterior

• General: DeckHot Tub
• Style: Contemporary

Construction

• Roofing: MetalStanding Seam
• General: Wood FrameStone ExteriorPoured Concrete

Location

• Road/Access: GravelPrivate Road
• HOA Amenities: Management PlanMaster InsuranceLandscapingCommon AcreageSnow RemovalTrash RemovalHOA FeeLandscapingPlowingTrash18527.36Yearly
• County: Rutland

Lot

• Driveway: Gravel
• Zoning: R01

Utilities

• Utilities: Cable Available
• Water: CommunityDrilled Well
• Sewer: Septic