300 Trailside Drive
300 Trailside Drive photo 2
300 Trailside Drive photo 3
300 Trailside Drive photo 4
300 Trailside Drive photo 5
300 Trailside Drive photo 6
300 Trailside Drive photo 7
300 Trailside Drive photo 8
300 Trailside Drive photo 9
300 Trailside Drive photo 10
300 Trailside Drive photo 11
300 Trailside Drive photo 12
300 Trailside Drive photo 13
300 Trailside Drive photo 14
300 Trailside Drive photo 15
300 Trailside Drive photo 16
300 Trailside Drive photo 17
300 Trailside Drive photo 18
300 Trailside Drive photo 19
300 Trailside Drive photo 20
300 Trailside Drive photo 21
300 Trailside Drive photo 22
300 Trailside Drive photo 23
300 Trailside Drive photo 24
300 Trailside Drive photo 25
300 Trailside Drive photo 26
300 Trailside Drive photo 27
300 Trailside Drive photo 28
300 Trailside Drive photo 29
300 Trailside Drive photo 30
300 Trailside Drive photo 31
300 Trailside Drive photo 32
300 Trailside Drive photo 33
300 Trailside Drive photo 34
300 Trailside Drive photo 35
300 Trailside Drive photo 36
300 Trailside Drive photo 37
300 Trailside Drive photo 38
300 Trailside Drive photo 39
300 Trailside Drive photo 40
300 Trailside Drive photo 41
300 Trailside Drive photo 42
300 Trailside Drive photo 43
300 Trailside Drive photo 44
300 Trailside Drive photo 45
300 Trailside Drive photo 46
300 Trailside Drive photo 47
300 Trailside Drive photo 48
48 photos

$1,850,000

300 Trailside Drive
Killington, VT 05751
Listed by Nathan Mastroeni · Elevations Real Estate
Bedrooms
2
Bathrooms
1
Living area
N/A
Year built
1982

About this home

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 two-bedroom, three-bath townhome 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 four-season rental, making it an attractive investment opportunity. Whether you’re looking for a mountain retreat, a revenue-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! Seller is offer clean slate for four bedrooms at closing. Schedule your private showing and make the mountain yours.

Property details

MLS #
5103728
Property type
Condominium
Subdivision
Trailside Village
Status
Active
Days on market
7
On market date
N/A
Stories
N/A
Garage spaces
N/A
Lot size
N/A
Loading map…

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$11,291/mo
$370,000 down
$1,480,000 loan
Principal & interest$9,599
Property tax (est.)$1,542
Home insurance (est.)$150

Similar homes you might like

Copyright 2026 PrimeMLS. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 08/12/26.