Listed by Nathan Mastroeni, Elevations Team - Real Broker LLC, (610) 574-6973 . 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
$1,683,000
Last Sold: Oct 9, 2025
9% below list $1.85M
$612/sqft
3 Beds
2.5 Baths
2,752 sqft
Homes for sale near 309 Trailside Drive
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Local Information
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Listed by Nathan Mastroeni
Elevations Team - Real Broker LLC, (610) 574-6973
Shannon Handrahan
Elevations Team - Real Broker LLC, (610) 574-6973
Bought with: Jacob Barnes, EXP Realty, (833) 388-2480
Source: PrimeMLS, MLS#5049853
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 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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from October 30, 2025
Home Highlights
Parking
Open Parking
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$612/sqft
Listed
180+ days ago
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 |
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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 | |
0.90 | Condo | $655,000 | 07/18/25 | 3 | 2 | 1,450 | |
1.32 | Condo | $630,000 | 08/27/25 | 3 | 3 | 1,300 | |
1.34 | Condo | $595,000 | 04/14/26 | 3 | 3 | 1,157 | |
1.34 | Condo | $544,500 | 07/03/25 | 3 | 2.5 | 1,168 | |
0.88 | Condo | $405,000 | 11/14/25 | 1 | 1 | 809 | |
1.61 | Condo | $580,000 | 01/23/26 | 2 | 2 | 1,266 |
Assigned Schools
These are the assigned schools for 309 Trailside Drive.
- Rutland Senior High School
- 9-12
- Public
- 752 Students
8/10GreatSchools RatingParent Rating AverageThey do a pretty decent job in terms of schooling but the overall experience at the school is not a good one in my opinion. If you have an opinion that others do not agree with, you will be shamed or bullied by multiple people. If you are not on a sports team, good luck getting any women. If you ARE a woman and happen to be overweight or not particularly good looking know that boys are ALWAYS talking behind your back insulting you. On the contrary, if you are an attractive woman and have big breasts or a big butt for example then you will be safe at this school, people do not attack you or sexually harass you. People will 100% talk about your body but they will never physically touch you.Overall the teachers are nice, it's the curriculum and the students that make it a bad school.Student Review4y ago - Rutland Town Elementary School
- PK-8
- Public
- 360 Students
7/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Killington Elementary School
- PK-6
- Public
- 111 Students
7/10GreatSchools 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 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
Learn more about our methodology.
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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 2026-05-09 07:14:46 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.
Homes for rent near 309 Trailside Drive
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Off Market Homes Near 309 Trailside Drive
SOLDMAY 1, 2026PrimeMLS, Closed- SOLDAPR 16, 2026PrimeMLS, Closed
- SOLDAPR 9, 2026PrimeMLS, Closed
- SOLDAPR 1, 2026
- SOLDMAR 31, 2026PrimeMLS, Closed
- SOLDMAR 6, 2026PrimeMLS, Closed
- SOLDJAN 12, 2026
- SOLDDEC 19, 2025PrimeMLS, Closed
- SOLDNOV 13, 2025PrimeMLS, Closed
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309 Trailside Drive, Killington, VT 05751 is a 3 bedroom, 3 bathroom, 2,752 sqft condo built in 1988. This property is not currently available for sale. 309 Trailside Drive was last sold on Oct 9, 2025 for $1,683,000 (9% lower than the asking price of $1,850,000).