300 Trailside Dr, Unit D

Killington, VT 05751

$2,750,000
Price
3
Beds
2,960 Sq. Ft.
$929 / Sq. Ft.
2,960
Sq. Ft.
$929
per Sq. Ft.
New
New

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...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.
  1. Listed by Nathan Mastroeni • Elevations Team - Real Broker LLC
  2. Listed by Shannon Handrahan • Elevations Team - Real Broker LLC

Property Details for 300 Trailside Drive, Unit D

Development / Subdivision
Trailside Village
Zoning
R01
LISTING UPDATED: 02/11/2026 05:22 PM

Property Details for 300 Trailside Drive, Unit D

StatusActive
MLS #5076313
Days on Market1
Taxes$11,915 / year
HOA Fees$18,527 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1982
Lot Size0.00 AC / 0 SF
CountyRutland County

Location

Listing Courtesy of Elevations Team - Real Broker LLC
Add your commute

Building Information for 300 Trailside Drive, Unit D

Stories2Year Built1982Building Size-Lot Size0.00 AC / 0 SF

Payment Calculator

$15,940 per month

30 year fixed, 6.15% Interest

Principal and Interest

$13,403

Property Taxes

$993

HOA Dues

$1,544

The Payment Calculator is for illustrative purposes only.

Property Information for 300 Trailside Drive, Unit D

Summary
Location and General Information
  • City: Killington
  • County: VT-Rutland
  • Directions: From Snowshed Base Lodge, take East Mountain Road, turn right after the great eastern bridge onto Trailside Drive. From Skyeship, take East Mountain Road, go past the Bear Mountain Access road, turn left onto Trailside Drive.
  • Latitude: 43.610346246606575
  • Longitude: -72.770124093254097
  • Road Frontage: No
  • Seasonal: No
  • State: VT
  • Street Designation: Drive
  • Zip Code: 05751
Taxes and HOA Information
  • Condo Fees: Yes
  • Fee: $18,527.36
  • Fee Frequency: Yearly
  • Fee Includes: Landscaping, Plowing, Trash, HOA Fee
  • SPAN Number: 558-185-12671
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Condo Development, Mountain View, Ski Area, Ski Trailside, Trail/Near Trail, View, Mountain, Near Golf Course, Near Skiing
  • Lot Size Acres: 0.0
Property and Assessments
  • Condo Name: Trailside Village
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Resort: Yes
  • Surveyed: Yes
  • Year Built: 1982
Utilities
  • Electric Company: Green Mountain Power
  • Fuel Company: CV oil
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Community, Drilled Well
  • Utilities: Cable Available
  • Internet: Fiber Optic Internet
Interior and Exterior Features
Exterior Features
  • Association Amenities: Management Plan, Master Insurance, Landscaping, Common Acreage, Snow Removal, Trash Removal
  • Construction Materials: Wood Frame, Stone Exterior
  • Roof: Metal, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Gas Stove, On Demand Water Heater
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Walkout
  • Flooring: Carpet, Wood
  • Heating: Propane, Baseboard, Heat Pump
  • Cooling: Mini Split
  • Total Stories: 2
Multi Family
Multi-Family Information
  • Units Per Building: 1

Property History for 300 Trailside Drive, Unit D

DateEvent & SourcePriceAppreciation
Feb 11, 2026

Listed (Active)

New England Real Estate Network #5076313

$2,750,000—
DateEvent & SourcePrice
02/11/2026

Listed (Active)

New England Real Estate Network #5076313

$2,750,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 300 Trailside Drive, Unit D

Taxable ValueLand-Additions-Total-
Home Facts
Beds0Lot Size43,560 SqFtStyleCondominiumCountyRUTLANDAPN(185) 12671

Schools near 300 Trailside Drive, Unit D

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
Killington Elementary School
Public - PK to 6
Woodstock Senior Uhsd #4
Public - 7 to 12
Killington Mountain School
Private - 7 to 12
Rating
School
Distance
Killington Elementary School
PublicPK to 6

Woodstock Senior Uhsd #4
Public7 to 12

Killington Mountain School
Private7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 300 Trailside Drive, Unit D, Killington, VT 05751

300 Trailside Drive, Unit D is a single family home for sale in Killington, VT 05751. This listing's school district is Windsor Central Unified Union School District. Nearby schools include Killington Elementary School, Woodstock Senior Uhsd #4 and Killington Mountain School. 300 Trailside Drive, Unit D is a 3-bed, 3-bath, 2,960 sqft single family home built in 1982.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Elevations Team - Real Broker LLC

Copyright 2026 PrimeMLS, 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 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 02/12/2026 08:47 AM