Coldwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Classic Realty
Property view
Listing view 2
Listing view 3

300 Trailside Drive, 
Killington, VT 05751

$2,750,000


3

Beds


3

Baths


2,960

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Nathan Mastroeni

Shannon Handrahan

Elevations Team - Real Broker LLC.

6744

610-574-6973

Last updated:

February 22, 2026, 11:25 AM

MLS#

5076313

Source:

PrimeMLS

About This Home

300 Trailside Drive

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.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1982

Price Summary

2,750,000

$929 per Sq. Ft.

MLS #:

5076313

Last Updated:

February 22, 2026, 11:25 AM

Added:

20 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

1

Interior

Living Area:

2,960 Sq. Ft.


Structure

Structure

Building Area:

2,960 Sq. Ft.

Year Built:

1982


Finances & Disclosures

Finances

Price:

$2,750,000

Price per Sq. Ft:

$929 per Sq. Ft.

MLS Logo
Copyright 2026 Prime MLS, Inc. 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 Prime MLS. The information being provided is for consumers’ personal, noncommercial 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 3, 2026

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.