Listed by Nathan Mastroeni, Elevations Real Estate, (802) 289-8463
300 Trailside Drive Unit D
Killington, VT 05751
2 Beds
3 Baths
2,960 sqft
2 Beds
3 Baths
2,960 sqft
Home Highlights
Parking
Open Parking
Climate Control
Heating & Cooling
Price/Sqft
$625
Listed
Less than a day ago
Local Information
- Map ViewExplore the area around 300 Trailside Drive Unit D.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: about 2 hours ago
Listing courtesy of Nathan Mastroeni
Elevations Real Estate, (802) 289-8463
Shannon Handrahan
Elevations Real Estate, (802) 289-8463
Source: PrimeMLS, MLS#5103728
Also Listed on PrimeMLS.
About this House
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 two-bedroom, three-bath townhome 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 four-season rental, making it an attractive investment opportunity. Whether you’re looking for a mountain retreat, a revenue-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.
Home Details for 300 Trailside Drive Unit D
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MLS Status: Active |
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Interior Details Basement: Finished,Walkout,Walk-Out AccessNumber of Rooms: 9 |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 2 |
Dimensions and Layout Living Area: 2960 Square Feet |
Appliances & Utilities Utilities: Cable Available, Fiber Optic Internt AvailAppliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer, Gas Stove, Instant Hot WaterDishwasherDryerLaundry: In BasementMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Propane,Baseboard,Heat PumpHas CoolingAir Conditioning: Mini SplitHas HeatingHeating Fuel: Propane |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Fireplace Screens/Equip, 1 FireplaceSpa: HeatedHas a FireplaceHas a Spa |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Wood |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoFloors: Carpet, Wood |
View Has a ViewView: Mountain(s) |
Room & Shared Space Shared space is furnished |
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Exterior Home Features Roof: Metal Standing SeamExterior: DeckFoundation: Concrete |
Parking & Garage No CarportNo GarageHas Open ParkingParking: Gravel,Driveway |
Frontage Road Frontage: None, Association, Private RoadRoad Surface Type: Gravel |
Water & Sewer Sewer: Community |
Finished Area Finished Area (above surface): 2960 Square Feet |
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Days on Market: <1 day on Trulia |
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Year Built Year Built: 1982 |
Property Type / Style Property Type: ResidentialProperty Subtype: CondominiumArchitecture: Contemporary |
Building Construction Materials: Wood Frame, Stone ExteriorNot a New Construction |
Property Information Not Included in Sale: A list will be provided once under contract. |
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Price List Price: $1,850,000Price Per Sqft: $625 |
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Direction & Address City: KillingtonCommunity: Trailside Village |
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Listing Agent Listing ID: 5103728 |
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Building Area Building Area: 2960 Square Feet |
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Units in Building: 1 |
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HOA Fee Includes: Maintenance Grounds, Plowing, Sewer, Trash, Water, HOA FeeHas an HOA |
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Furnished |
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BasementMls Number: 5103728Additional Fee Info: Fee: $1599.96Above Grade Unfinished Area: 2960Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square Feet |
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HOA Amenities: Management Plan,Master Insurance,Landscaping,Common Acreage,Snow Removal,Trash Removal |
Market trends in Killington
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
Price History for 300 Trailside Drive Unit D
| Date | Price | Event | Source |
|---|---|---|---|
| 08/06/2026 | $1,850,000 | Listed For Sale | PrimeMLS #5103728 |
| 04/23/2026 | $2,750,000 | ListingRemoved | PrimeMLS #5076313 |
| 02/11/2026 | $2,750,000 | Listed For Sale | PrimeMLS #5076313 |
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Comparable Sales for 300 Trailside Drive Unit D
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.06 | Condo | $1,683,000 | 10/09/25 | 3 | 2.5 | 2,752 | |
0.88 | Condo | $885,000 | 04/16/26 | 3 | 3 | 1,715 | |
0.87 | Condo | $840,000 | 09/03/25 | 4 | 3 | 2,085 | |
0.91 | Condo | $879,000 | 03/31/26 | 4 | 3 | 2,067 | |
1.27 | Condo | $630,000 | 08/27/25 | 3 | 3 | 1,300 | |
1.29 | Condo | $595,000 | 04/14/26 | 3 | 3 | 1,157 | |
0.94 | Condo | $405,000 | 11/14/25 | 1 | 1 | 809 | |
1.45 | Condo | $815,000 | 07/16/26 | 2 | 2 | 1,342 | |
1.53 | Condo | $450,000 | 04/30/26 | 2 | 2.5 | 1,090 | |
1.39 | Condo | $350,000 | 05/01/26 | 2 | 2 | 881 |
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Assigned Schools
These are the assigned schools for 300 Trailside Drive Unit D.
- Woodstock Senior Uhsd #4
- 7-12
- Public
- 440 Students
9/10GreatSchools RatingParent Rating AverageIt's a really good school. I went here for 7th grade (I'm moving to Florida now). There was this 9th grader who I went to elementary school with, and all through elementary school, he terrorized me when I literally did nothing to him (you know who you are). After he recognized me when I got into this school, he started being a jerk again and would say something mean and/or stupid every time he walked by me. I went and told my counselor (the counselors there are amazing) and she made it very clear that they don't tolerate bullying and that he wasn't going to bother me. After that he bothered me one more time, but when he got told he was on serious warning of suspension, he stopped. That's the main reason for me [kind of] liking this school. They stay on top of bullying issues. Also, the staff are amazing, you don't get loaded with stress and homework. It's easy to get around and navigate, and the classes are a lot of fun. I really like how they have basically no rules at that school but you don't see kids smoking or doing graffiti or things like that. Something that wasn't so good about my time there (and know that this is really my problem, not the school's, that's why the rating is 5 stars) is the other kids. As if the [I'm not saying what he is since kids read this stuff] wasn't bad enough, most of the kids in my grade were just kind of rude. I've always been kind of socially awkward and never really had a lot of friends, and I sometimes get the feeling that other kids will have more fun if I'm not there, so I don't really talk to them unless I have to (like if we get paired together for an assignment). And obviously they don't have any reason to be rude (since I don't talk to them), but when we have to do classwork together, they're really picky about everything (if we make a poster everything HAS to be perfect) and they get all snappy if I do one thing they don't like. I did have a couple friends that were amazing, though. Sorry if this felt more like a rant about my social life; I know I didn't give a lot of helpful information, but that's just what I typed I guess. In short it's an amazing school. For the actual school, 5 stars. For my social experience, 1.5 stars.Other Review5y ago - Killington Elementary School
- PK-6
- Public
- 112 Students
9/10GreatSchools RatingParent Rating AverageThis is the first year my grandchildren are at Killington Elementary School. I am so thrilled. One who struggles academically, one who has always been ahead academically and they are both thriving! Thanks to the wonderful staff and environment there both of my grandkids are so happy and moving forward academically as well as socially. What a wonderful feeling to have them talk so positively about school and to see their progress. Many thanks to the amazing teachers there! From a grandma and former fourth grade teacher!Other Review11y ago 
Check out schools near 300 Trailside Drive Unit D.
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
Nathan Mastroeni, Elevations Real Estate, (802) 289-8463
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 2026-08-06 09:35:02 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.
300 Trailside Drive Unit D, Killington, VT 05751 is a 2 bedroom, 3 bathroom, 2,960 sqft condo built in 1982. This property is currently available for sale and was listed by PrimeMLS on Aug 6, 2026. The MLS # for this home is MLS# 5103728.