Live where the Green Mountains are your backyard. This 4-bedroom chalet-style home sits on 1.23 acres in Killington, close to some of the best four-season recreation in the East. In winter, when the leaves drop, you get mountain views through the trees. Killington Resort, the largest ski area in the East, is a short drive away, with seven peaks, hundreds of acres of terrain, and a ski season that often starts in October and runs well into spring. Pico Mountain is also close, a favorite for its old-school Vermont feel, family-friendly trails, and smaller crowds. When the snow melts, the area turns to mountain biking, hiking, golf, and fishing. The Green Mountain National Forest is nearby, with miles of trails for hiking, snowshoeing, cross-country skiing, and snowmobiling. The Long Trail and Appalachian Trail cross Route 4 at Sherburne Pass, giving you easy access to day hikes with big views. Kent Pond, Gifford Woods State Park, and the Ottauquechee River are close for paddling, swimming, and fall foliage. After a day outside, Killington’s restaurants, breweries, and après-ski spots are close, and Rutland is an easy drive for groceries, dining, and shopping. Woodstock, Okemo, and Quechee are all within a day trip. The home has been updated with fresh paint, a new staircase, new kitchen cabinets, and a new heating system, so you can spend your time enjoying the area. It’s a good fit as a full-time home, a ski-season getaway, or a rental.
Active
Listed by: Elevations Real Estate • Nathan Mastroeni • 802-289-8463
$559,000
303 Winding Way, Killington, VT 05751
4beds
1,776sqft
Single Family Residence
Built in 1970
1.23 Acres Lot
$-- Zestimate®
$315/sqft
$-- HOA
What's special
New heating systemNew staircaseNew kitchen cabinetsUpdated with fresh paint
- 17 hours
- 243
- 11
Zillow last checked:
Listing updated:
Listed by:
Nathan Mastroeni,
Elevations Real Estate 802-289-8463
Source: PrimeMLS,MLS#: 5115977
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 3/4 bathrooms: 1
Heating
- Propane, Baseboard
Cooling
- None
Appliances
- Included: Dryer, Microwave, Refrigerator, Washer, Gas Stove
Features
- Natural Light
- Flooring: Carpet
- Has basement: No
Interior area
- Total structure area: 1,776
- Total interior livable area: 1,776 sqft
- Finished area above ground: 1,776
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Parking features: Gravel
Features
- Levels: Two
- Stories: 2
- Exterior features: Deck
- Has spa: Yes
- Spa features: Heated
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 1.23 Acres
- Features: Sloped
Details
- Parcel number: 58818510199
- Zoning description: residential
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Chalet
- Property subtype: Single Family Residence
Materials
- Other
- Foundation: Block
- Roof: Shingle
Condition
- New construction: No
- Year built: 1970
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Septic Tank
- Utilities for property: Other
Community & HOA
Location
- Region: Killington
Financial & listing details
- Price per square foot: $315/sqft
- Tax assessed value: $222,090
- Annual tax amount: $5,886
- Date on market: 10/28/2026
Estimated market value
Not available
Estimated sales range
Not available
$2,571/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/28/2026 | Listed for sale | $559,000+2.8%$315/sqft |
Source: | ||
| 10/23/2026 | Listing removed | -- |
Source: Owner Report a problem | ||
| 10/21/2026 | Price change | $544,000-8.6%$306/sqft |
Source: Owner Report a problem | ||
| 10/16/2026 | Listed for sale | $595,000+2.6%$335/sqft |
Source: Owner Report a problem | ||
| 10/14/2026 | Listing removed | $579,900$327/sqft |
Source: | ||
| 10/12/2026 | Pending sale | $579,900$327/sqft |
Source: | ||
| 10/5/2026 | Price change | $579,900-1.7%$327/sqft |
Source: | ||
| 9/28/2026 | Price change | $589,900-1.7%$332/sqft |
Source: | ||
| 9/23/2026 | Price change | $599,900-2.6%$338/sqft |
Source: | ||
| 9/2/2026 | Price change | $615,900-1.4%$347/sqft |
Source: | ||
| 8/27/2026 | Price change | $624,900-3.8%$352/sqft |
Source: | ||
| 8/12/2026 | Price change | $649,500+3.3%$366/sqft |
Source: | ||
| 7/9/2026 | Price change | $629,000+14.4%$354/sqft |
Source: | ||
| 6/17/2026 | Price change | $549,900-1.8%$310/sqft |
Source: | ||
| 5/30/2026 | Listed for sale | $559,900$315/sqft |
Source: | ||
| 5/30/2026 | Pending sale | $559,900$315/sqft |
Source: | ||
| 5/20/2026 | Listed for sale | $559,900-1.6%$315/sqft |
Source: | ||
| 5/15/2026 | Listing removed | $569,000$320/sqft |
Source: | ||
| 5/6/2026 | Price change | $569,000-0.9%$320/sqft |
Source: | ||
| 4/25/2026 | Price change | $574,000-0.9%$323/sqft |
Source: | ||
| 4/6/2026 | Price change | $579,000-3.3%$326/sqft |
Source: | ||
| 1/15/2026 | Price change | $599,000+5.1%$337/sqft |
Source: | ||
| 12/14/2025 | Price change | $569,900+11.8%$321/sqft |
Source: Owner Report a problem | ||
| 12/8/2025 | Pending sale | $509,900$287/sqft |
Source: Owner Report a problem | ||
| 12/7/2025 | Listed for sale | $509,900+50%$287/sqft |
Source: Owner Report a problem | ||
| 12/24/2024 | Sold | $340,000$191/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $222,090 |
| 2023 | -- | $222,090 |
| 2022 | -- | $222,090 |
| 2021 | -- | $222,090 |
| 2020 | -- | $222,090 |
| 2019 | -- | $222,090 |
| 2018 | -- | $222,090 |
| 2017 | -- | $222,090 |
| 2016 | -- | $222,090 +9904.1% |
| 2015 | -- | $2,220 |
| 2014 | -- | $2,220 |
| 2013 | -- | $2,220 0% |
| 2012 | -- | $2,221 |
| 2011 | -- | $2,221 +26.9% |
| 2010 | -- | $1,750 |
| 2009 | -- | $1,750 |
Find assessor info on the county website
Monthly payment
Est. payment




