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 Tools

More Info

Tax Information

  • Tax Year2025

Parking

  • Parking Spaces
  • GarageNo

Rooms

  • Full Bath1

Basic Information

  • MLS Number5076313
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$2,750,000
  • Listing Agent NameNathan Mastroeni
  • Unit NumberD
  • Broker NameElevations Team - Real Broker LLC

Location

  • Building Number300
  • StreetTrailside Drive
  • TownKillington
  • StateVT
  • Zip05751
  • CountyRutland
  • SubdivisionTrailside Village
  • Elementary SchoolKillington Elementary School
  • Junior HighChoice
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address300 Trailside Drive

Building

  • Year Built1982
  • Building ConstructionWood Frame, Stone Exterior
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms3
  • Bathroom3
  • Total Baths3
  • 3/4 Baths2
  • Total Rooms9
  • Square Feet2,960
  • BasementWalkout
  • FoundationPoured Concrete

Property

  • Lot DescriptionCondo Development, Mountain View, Ski Area, Ski Trailside, Trail/Near Trail, View, Mountain, Near Golf Course, Near Skiing
  • AreaVT-Rutland
  • DrivewayGravel
  • RoadsGravel, Private Road

Interior

  • Interior FeaturesCathedral Ceiling, Dining Area, Fireplace Screens/Equip,1 Fireplace, Furnished, Hot Tub, Kitchen/Dining, Natural Light, Sauna, Basement Laundry
  • FloorsCarpet, Wood
  • Stories2

Exterior

  • Exterior FeaturesDeck, Hot Tub
  • RoofMetal, Standing Seam

Utilities

  • Heat SystemPropane, Baseboard, Heat Pump
  • WaterCommunity, Drilled Well
  • SewerSeptic
  • ElectricCircuit Breaker(s)
  • UtilitiesCable Available

Amenities

  • PricePerSqFt929.05

Other

  • SeasonalNo
  • Page874-875
  • Date Listed02/11/2026

Map Location

Listed by Nathan Mastroeni of Elevations Team - Real Broker LLC
Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated March 14, 2026 9:37 PM EDT

 

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