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
-- mins to
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
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MLS Status: Closed |
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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 |
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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 |
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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 |
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Price List Price: $1,850,000Price Per Sqft: $612/sqft |
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Direction & Address City: Killington |
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Building Area Building Area: 2752 Square Feet |
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Units in Building: 1 |
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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 |
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HOA Amenities: Maintenance Structure,Management Plan,Master Insurance,Landscaping,Common Acreage,Security,Snow Removal,Trash Removal |
Price History for 309 Trailside Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 10/09/2025 | $1,683,000 | Sold | PrimeMLS #5049853 |
| 07/03/2025 | $1,850,000 | Listed For Sale | PrimeMLS #5049853 |
| 11/20/2023 | ListingRemoved | PrimeMLS #4955796 | |
| 06/06/2023 | $2,100,000 | Listed For Sale | PrimeMLS #4955796 |
| 05/22/2023 | ListingRemoved | N/A | |
| 02/07/2023 | $2,250,000 | Listed For Sale | N/A |
| 03/21/2021 | ListingRemoved | PrimeMLS #4849770 | |
| 03/06/2021 | $1,760,000 | Listed For Sale | PrimeMLS #4849770 |
Market trends in Killington
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
Property Tax and Assessment
| Year | 2024 |
|---|---|
| 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.Assigned Schools
These are the assigned schools for 309 Trailside Drive.
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
LGBTQ Local Legal Protections
Apartments for Rent
Homes for sale near 309 Trailside Drive
Off Market Homes Near 309 Trailside Drive
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.
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.

