309 Trailside Dr

Killington, VT 05751

$1,683,000
Last Sold Price
3
Beds
2,752 Sq. Ft.
$612 / Sq. Ft.
2,752
Sq. Ft.
$612
per Sq. Ft.
Closed 10/9/25
Closed 10/9/25

Description

Ski-in, ski-out home on Great Eastern at Killington directly on a nice warm up run down to the SkyeShip gondola, this home provides easy access to everything Killington Resort has to offer; a rare find! The interior has been completely renovated and features fresh paint throughout, all new windows and doors. The exterior facade has been updated with stone, thermal insulation wall panels, and a brand-new composite fiberglass-reinforced plastic back deck—stronger than steel and requiring no painting...Ski-in, ski-out home on Great Eastern at Killington directly on a nice warm up run down to the SkyeShip gondola, this home provides easy access to everything Killington Resort has to offer; a rare find! The interior has been completely renovated and features fresh paint throughout, all new windows and doors. The exterior facade has been updated with stone, thermal insulation wall panels, and a brand-new composite fiberglass-reinforced plastic back deck—stronger than steel and requiring no painting or staining. The new standing seam roof is built to last. The spacious Great Room, with cathedral ceilings and a wood fireplace, serves as the heart of the home, while the open kitchen and dining areas make entertaining a pleasure. The two-story primary suite occupies the entire west side, with two guest bedrooms on the east. Circular stairs lead up to a versatile loft, ideal for a game room or library, and a private loft above the primary suite can be used as an office, studio, or large walk-in closet. Additional amenities include a sauna, shower room, outdoor hot tub, and mini splits for AC and heat throughout the house, ensuring comfort no matter the season. Nestled in the woods but overlooking Bear Mountain Valley, this property offers privacy combined with convenience. Perfect for skiing, riding, hiking, biking enthusiasts, or investors seeking a slopeside property to enjoy or lease. Discover all the opportunities of the trailside lifestyle
  1. Listed by Nathan Mastroeni • Elevations Team - Real Broker LLC
  2. Listed by Shannon Handrahan • Elevations Team - Real Broker LLC

Sold By EXP Realty

Property Details for 309 Trailside Drive

Zoning
Residential 3
LISTING UPDATED: 10/30/2025 01:51 PM

Property Details for 309 Trailside Drive

StatusClosed
MLS #5049853
Days on Market83
Taxes$10,738 / year
HOA Fees$1,511 / month
Condo/Co-op Fees-
Compass TypeCondo
MLS TypeResidential / Condo
Year Built1988
CountyRutland County

Location

Add your commute

Building Information for 309 Trailside Drive

Building/ComplexTrailside VillageFloor-Stories1Residences1Pet Policy-Pet Policy Details-Year Built1988

Payment Calculator

$10,608 per month

30 year fixed, 6.15% Interest

Principal and Interest

$8,203

Property Taxes

$895

HOA Dues

$1,511

The Payment Calculator is for illustrative purposes only.

Property Information for 309 Trailside Drive

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, turn left after the Bear Mountain Access Road. Once on Trailside Drive, the property is the first home on the left.
  • Latitude: 43.609466000000999
  • Longitude: -72.769845000000004
  • Road Frontage: No
  • Seasonal: No
  • State: VT
  • Street Designation: Drive
  • Zip Code: 05751
Taxes and HOA Information
  • Condo Fees: Yes
  • Fee: $1,511.09
  • Fee Frequency: Monthly
  • SPAN Number: 588-185-12669
  • Tax Year: 2024
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Condo Development, Ski Area, Ski Trailside
  • Lot Size Acres: 0.0
Property and Assessments
  • Condo Name: Trailside Village
  • Property Class: Residential
  • Property Type: Condo
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1988
Utilities
  • Electric Company: Green Mountain Power
  • Fuel Company: CV Oil
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Community, Drilled Well
  • Utilities: Phone, Cable
  • Internet: Fiber Optic Internet
Interior and Exterior Features
Exterior Features
  • Association Amenities: Building Maintenance, Management Plan, Master Insurance, Landscaping, Common Acreage, Security, Snow Removal, Trash Removal
  • Construction Materials: Masonry, Stone Exterior, Wood Siding
  • Roof: Standing Seam
Interior Features
  • Basement: No
  • Flooring: Manufactured
  • Heating: Propane, Baseboard, Mini Split
  • Cooling: Mini Split
  • Total Stories: 1.5
Multi Family
Multi-Family Information
  • Units Per Building: 1

Property History for 309 Trailside Drive

DateEvent & SourcePriceAppreciation
Oct 9, 2025

Sold

New England Real Estate Network #5049853

$1,683,000—
Oct 9, 2025

Pending

New England Real Estate Network #5049853

—
Sep 24, 2025

Active Under Contract

New England Real Estate Network #5049853

—
Jul 3, 2025

Listed (Active)

New England Real Estate Network #5049853

$1,850,000—
Nov 20, 2023

Expired

New England Real Estate Network #4955796

—
Jun 5, 2023

Listed (Active)

New England Real Estate Network #4955796

$2,100,000—
DateEvent & SourcePrice
10/09/2025

Sold

New England Real Estate Network #5049853

$1,683,000
10/09/2025

Pending

New England Real Estate Network #5049853

—
09/24/2025

Active Under Contract

New England Real Estate Network #5049853

—
07/03/2025

Listed (Active)

New England Real Estate Network #5049853

$1,850,000
11/20/2023

Expired

New England Real Estate Network #4955796

—
06/05/2023

Listed (Active)

New England Real Estate Network #4955796

$2,100,000

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

Schools near 309 Trailside Drive

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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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 01/25/2026 10:35 PM