Listed by Bret Williamson, Killington Valley Real Estate, (802) 422-3610 . Bought with Killington Valley Real Estate
123 Trailside Drive
Killington, VT 05751
5 Beds
5.5 Baths
6,048 sqft (on 0.90 acres)
$4,584,000
as of Jun 20, 2026
$4,584,000
as of Jun 20, 2026
5 Beds
5.5 Baths
6,048 sqft
(on 0.90 acres)
Local Information
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Last check for updates: about 21 hours ago
Listed by Bret Williamson
Killington Valley Real Estate, (802) 422-3610
Bought with: Bret Williamson, Killington Valley Real Estate, (802) 422-3610
Source: PrimeMLS, MLS#4944367
Description
Here is a rare opportunity to own a brand-new 5-bedroom, 5.5-bath luxury property with ski-on, ski-off access to the Great Eastern trail in Killington Resort. Relax après ski in the 7-person hot tub, the sauna, or by the wood-burning natural stone fireplace in the great room with vaulted 24-foot ceilings with timber beams. Custom woodwork throughout, including solid alder wood interior doors and high ceilings. The commercial kitchen features custom Schuler cabinets, stone countertops, Thermador appliances, a six-burner stove, instant boiling water, wine cooler and a second refrigerator in the pantry. More than 100 recessed lights throughout the home provide ample lighting. Other amenities include a mudroom with built-in boot drying system, water softener, security system, basement bar & billiards room, exterior hot and cold water faucets, a clawfoot tub in the primary bathroom and a heated oversized 2 car garage. Exterior highlights include a lighted driveway, natural landscaping with apple trees and a boulder stone wall. Built for efficiency with Anderson A-Series windows and additional insulation—R-58 in the ceilings and R28 in the walls and a two-zone HVAC system to keep it comfortable year round. 123 Trailside Drive is unique in the market, call for more information or a private showing of this one of a kind slope side retreat. Showings to start April 1, 2023 by appointment.
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 June 10, 2024
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 123 Trailside Drive
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MLS Status: Closed |
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Interior Details Basement: Finished,Full,Insulated,Interior Stairs,Walkout,Interior Access,Interior EntryNumber of Rooms: 10 |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 6048 Square Feet |
Appliances & Utilities Utilities: Cable Available, PropaneAppliances: Dishwasher, Dryer, Microwave, Gas Range, Refrigerator, Washer, Gas Stove, Gas Water Heater, Wine Cooler, Exhaust FanDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Propane,Wood,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Propane |
Fireplace & Spa Fireplace: Wood BurningSpa: HeatedHas a FireplaceHas a Spa |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Window: Low Emissivity WindowsFlooring: Ceramic Tile, Hardwood, Wood |
Levels, Entrance, & Accessibility Stories: 3Levels: 3Floors: Ceramic Tile, Hardwood, Wood |
View No View |
Security Security: Security, Carbon Monoxide Detector(s), Security System, HW/Batt Smoke Detector |
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Exterior Home Features Roof: Metal Architectural ShingleExterior: Sauna, StorageFoundation: Concrete |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Gravel,Direct Entry,Heated Garage,Driveway,Garage,On Site,Attached |
Frontage Road Surface Type: GravelNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
Farm & Range Frontage Length: Road frontage: 175 |
Finished Area Finished Area (above surface): 4644 Square FeetFinished Area (below surface): 1404 Square Feet |
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Year Built Year Built: 2023 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary |
Building Construction Materials: Wood Frame, Stone ExteriorIs a New Construction |
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Price List Price: $3,499,000 |
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Direction & Address City: Killington |
School Information Elementary School: Killington Elementary SchoolElementary School District: WindsorJr High / Middle School: Woodstock Union Middle SchoolJr High / Middle School District: WindsorHigh School: Woodstock Union High SchoolHigh School District: Windsor |
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Building Area Building Area: 7258 Square Feet |
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Lot Area: 0.90 acres |
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BasementMls Number: 4944367Above Grade Unfinished Area: 4644Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 100Below Grade Unfinished Area Source: OwnerBelow Grade Unfinished Area Units: Square Feet |
Price History for 123 Trailside Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 10/31/2023 | $3,751,000 | Sold | PrimeMLS #4944367 |
| 03/11/2023 | $3,499,000 | Contingent | PrimeMLS #4944367 |
| 03/01/2023 | $3,499,000 | Listed For Sale | PrimeMLS #4944367 |
| 03/04/2021 | $380,000 | Sold | PrimeMLS #4829484 |
Market trends in Killington
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
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Homeowner tools
Estimated monthly rent$7,290/mo
Comparable Sales for 123 Trailside Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.43 | Single-Family Home | $4,300,000 | 04/13/26 | 5 | 4.5 | 4,826 | |
0.43 | Single-Family Home | $1,975,000 | 12/19/25 | 5 | 4.5 | 4,316 | |
0.20 | Single-Family Home | $1,375,000 | 05/01/26 | 3 | 3.5 | 2,718 | |
2.03 | Single-Family Home | $905,000 | 09/19/25 | 4 | 3 | 2,730 | |
2.32 | Single-Family Home | $1,200,000 | 11/19/25 | 5 | 2.5 | 3,696 | |
2.20 | Single-Family Home | $1,390,000 | 03/06/26 | 4 | 6.5 | 6,269 | |
2.59 | Single-Family Home | $1,150,000 | 04/09/26 | 5 | 3.5 | 3,182 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDOCT 9, 2025PrimeMLS, Closed
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SOLDMAY 1, 2026PrimeMLS, Closed
SOLDDEC 19, 2025PrimeMLS, Closed
SOLDAPR 13, 2026PrimeMLS, Closed
Assigned Schools
These are the assigned schools for 123 Trailside Drive.
- 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 Review4y 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 123 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.
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Homes for sale near 123 Trailside Drive
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Off Market Homes Near 123 Trailside Drive
- SOLDAPR 13, 2026PrimeMLS, Closed
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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 2026-06-19 11:55:48 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.
123 Trailside Drive, Killington, VT 05751 is a 5 bedroom, 6 bathroom, 6,048 sqft single-family home built in 2023. This property is not currently available for sale. 123 Trailside Drive was last sold on Oct 31, 2023 for $3,751,000 (7% higher than the asking price of $3,499,000). The current Trulia Estimate for 123 Trailside Drive is $4,584,000.