300 Trailside Drive # D Killington, VT $ 2,750,000
300 Trailside Drive # D
$ 2,750,000
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300 Trailside Drive # D

Killington, VT, 05751
$ 2,750,000
Bedrooms3 Baths3.0 Sq 2,960

Monthly Estimate*

$ 16,932

Listed by Nathan Mastroeni, Elevations Team - Real Broker LLC, 610-574-6973, Nathan@ElevationsVT.com
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Single Family Home for sale in Killington, VT

for $2,750,000 with 3 bedrooms and 3 full baths. This 2,960 square foot home was built in 1982.

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.

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Single Family Active

Price

$ 2,750,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 0

Style

Contemporary

Year Built

1982

Town/City

Killington

County/Region

Rutland

MLS | Web ID

5076313

Features
Interior
Basement Description Walkout
Interior Amenities Cathedral Ceiling Dining Area Fireplace Screens/Equip 1 Fireplace Furnished Hot Tub Kitchen/Dining Natural Light Sauna Basement Laundry
Basement Yes
Flooring Carpet Wood
Beds 3
Total Rooms 9
Total Number of Units 1
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General
Road Frontage No
Sewer Septic
Heating Propane Baseboard Heat Pump
Cooling Mini Split
Utilities Cable Available
Roof Metal Standing Seam
Appliances Dishwasher Dryer Microwave Refrigerator Washer Gas Stove On Demand Water Heater
Garage No
Flood Zone No
Zoning R01
HOA Fee 18527.36
Exclusions A list will be provided upon going under contract.
3/4 Baths 2
Full Baths 1
Half Baths 0
Bathrooms 3
Year Built 1982
Electric Circuit Breaker(s)
Subdivision Trailside Village
Style Contemporary
Stories Count 2
Construction Status Existing
Type Single Family
Condo Name Trailside Village
Unit Number D
Auction No
Tax Year 2025
Condo Fees Yes
Assoc Fee Paid Per Yearly
Status Detail 0
Covenants Yes
Construction Materials Wood Frame Stone Exterior
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
High School Choice
City Killington
Seasonal No
Elementary School Killington Elementary School
Middle School Choice
DOM 6
Price Per Sq Ft Total AG 929.05
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Exterior
Lot Features Condo Development Mountain View Ski Area Ski Trailside Trail/Near Trail View Mountain Near Golf Course Near Skiing
Exterior Amenities Deck Hot Tub
Driveway Gravel
Lot Size Area 0
Water Source Community Drilled Well
Foundation Poured Concrete
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* Excluded Features
List By
Nathan Mastroeni

Listing Agent

Elevations Team - Real Broker Llc

Broker

(610) 574-6973

Phone

Nathan@ElevationsVT.com

Email

Affordability Calculator

$16,932
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Monthly Principal & Interest
$16,932
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
5398504 Elementary School
449202 Middle School
Choice High School High School
Pricing History
DatePricePrice ChangeDescription
2/11/2026$2,750,000 Listed Price

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300 Trailside Drive # D, Killington, VT, 05751 is a Single Family Home for sale at $2,750,000 with 2,960 sqft. 300 Trailside Drive # D has 3 bedrooms, 3.0 baths, and was built in 1982. The property's zip code is 05751 which is in Killington, VT