309 Trailside Drive, Killington, VT 05751
Property image
Property image
SOLD
OCT 9, 2025
Listed by Nathan Mastroeni, Elevations Team - Real Broker LLC, (802) 289-8463 . Bought with EXP Realty

309 Trailside Drive
Killington, VT 05751

  • 3 Beds
  • 2.5 Baths
  • 2,752 sqft

$1,683,000

Last Sold: Oct 9, 2025
9% below list $1.85M
$612/sqft
Est. Refi. Payment $11,417/mo*

$1,683,000

Last Sold: Oct 9, 2025
9% below list $1.85M
$612/sqft
Est. Refi. Payment $11,417/mo*
3 Beds
2.5 Baths
2,752 sqft

Local Information

  • Map ViewExplore the area around 309 Trailside Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1988
Living Area
2,752 sqft
Price/Sqft
$612/sqft
Parking
Open Parking
Last check for updates: about 11 hours ago
Listed by Nathan Mastroeni
Elevations Team - Real Broker LLC, (802) 289-8463
Shannon Handrahan
Elevations Team - Real Broker LLC, (802) 289-8463
Bought with: Jacob Barnes, EXP Realty, (833) 388-2480
Source: PrimeMLS, MLS#5049853

About this House

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
309 Trailside Drive, Killington, VT 05751 is a 3 bedroom, 3 bathroom, 2,752 sqft condo built in 1988. It last sold for $1,683,000 on Oct 9, 2025 (9% below the $1,850,000 asking price). It is currently off market. The Trulia Estimate is $1,721,000, with a rent estimate of $3,541/month.

Home Details for 309 Trailside Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Number of Rooms: 8
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (quarter): 1
Dimensions and Layout
Living Area: 2752 Square Feet
Appliances & Utilities
Utilities: Phone, CableLaundry: 1st Floor Laundry
Heating & Cooling
Heating: Propane,Baseboard,Mini SplitHas CoolingAir Conditioning: Mini SplitHas HeatingHeating Fuel: Propane
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood Burning, 1 FireplaceSpa: HeatedHas a FireplaceHas a Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Skylight(s)Flooring: Manufactured
Levels, Entrance, & Accessibility
Stories: 1.5Levels: One and One HalfFloors: Manufactured
View
No View

Exterior Features

Exterior Home Features
Roof: Standing SeamExterior: DeckFoundation: Concrete Slab
Parking & Garage
No CarportNo GarageHas Open ParkingParking: Gravel,Driveway
Frontage
Road Frontage: NoneRoad Surface Type: Gravel, Paved
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2752 Square Feet

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: CondominiumArchitecture: Contemporary
Building
Building Name: Trailside VillageConstruction Materials: Masonry, Stone Exterior, Wood SidingNot a New Construction

Price & Status

Price
List Price: $1,850,000Price Per Sqft: $612/sqft

Location

Direction & Address
City: Killington

Building

Building Area
Building Area: 2752 Square Feet

Community

Units in Building: 1

Miscellaneous

Mls Number: 5049853Additional Fee Info: Fee: $1511.09Above Grade Unfinished Area: 2752Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Additional Information

HOA Amenities: Maintenance Structure,Management Plan,Master Insurance,Landscaping,Common Acreage,Security,Snow Removal,Trash Removal

Price History for 309 Trailside Drive

DatePriceEventSource
10/09/2025$1,683,000Sold
PrimeMLS #5049853
07/03/2025$1,850,000Listed For SalePrimeMLS #5049853
11/20/2023ListingRemovedPrimeMLS #4955796
06/06/2023$2,100,000Listed For SalePrimeMLS #4955796
05/22/2023ListingRemovedN/A
02/07/2023$2,250,000Listed For SaleN/A
03/21/2021ListingRemovedPrimeMLS #4849770
03/06/2021$1,760,000Listed For SalePrimeMLS #4849770

Market trends in Killington

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
34
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax
Assessment$330,000
Home facts updated by county records

Comparable Sales for 309 Trailside Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.83
Condo
$885,000
04/16/26
3
3
1,715
0.83
Condo
$840,000
09/03/25
4
3
2,085
0.86
Condo
$879,000
03/31/26
4
3
2,067
1.32
Condo
$630,000
08/27/25
3
3
1,300
1.34
Condo
$595,000
04/14/26
3
3
1,157
1.50
Condo
$815,000
07/16/26
2
2
1,342
0.88
Condo
$405,000
11/14/25
1
1
809
1.50
Condo
$840,000
08/03/26
2
2
1,055
1.43
Condo
$412,250
06/24/26
3
2
827

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 309 Trailside Drive.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Killington

At least 10 Trulia users voted on each feature.
  • 88 % Say car is needed

  • 83 % Say it's quiet

  • 81 % Say it's dog friendly

  • 74 % Say there's holiday spirit

  • 73 % Say they plan to stay for at least 5 years

  • 71 % Say parking is easy

  • 67 % Say there's wildlife

  • 67 % Say people would walk alone at night

  • 58 % Say there are community events

  • 57 % Say yards are well-kept

  • 54 % Say kids play outside

  • 50 % Say it's walkable to restaurants

  • 47 % Say streets are well-lit

  • 43 % Say neighbors are friendly

  • 40 % Say there are sidewalks

  • 18 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Washer/dryer

Homes for sale near 309 Trailside Drive

Skip to last item
Skip to first item

Off Market Homes Near 309 Trailside Drive

Skip to last item
Skip to first item

Frequently asked questions about 309 Trailside Drive

  • What is 309 Trailside Drive estimated to be worth?
    Trulia's estimated value for 309 Trailside Drive in Killington, VT is $1,721,000.
  • What is the price history for 309 Trailside Drive?
    309 Trailside Drive in Killington, VT last sold for $1,683,000 in October 2025.
  • Is Killington a buyer's or seller's market?
    Killington is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Killington?
    Residents describe Killington, VT as quiet, dog-friendly, and established. Most residents say you need a car. See recently sold homes in Killington, VT.
  • Does 309 Trailside Drive have air conditioning?
    Yes, 309 Trailside Drive in Killington, VT has air conditioning.
  • Does 309 Trailside Drive have laundry facilities?
    Yes, 309 Trailside Drive in Killington, VT has laundry facilities.
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 2026-08-07 12:13:54 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.