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Listed by: Nathan Mastroeni | Elevations Real Estate (802) 289-8463
$559,000
Monthly Est:$2,782
4 Beds
- 3 Baths
2 full baths
1,776sqft
303 Winding Way, Killington, VT 05751
$559,000
$2,782/moEst:
Get Pre-Approved
Single Family Residence
Built in 1970
$-- HOA
1.23 acres lot
$315/sq.ft
Description
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.
- Houzeo last checked: 12 hours ago
- Listing updated: October 28, 2026 at 4:49 pm
- Source: NEREN/Prime MLS-NH | MLS#: 5115977

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1970
HOA Fees
-
Finished Area
1,776 sqft
Lot Size
1.23 acres lot
Basement Area
- sqft
MLS Name
NEREN/Prime MLS
MLS Number
5115977
MLS Status
(10) Active - Active
Days on Market
6

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 3
Interior
Appliances
Dryer, Microwave, Refrigerator, Washer, Gas Stove
Exterior Features
Deck, Hot Tub
Interior Features
Natural Light
Flooring
Carpet
Heating
Propane, Baseboard
Sewer
Septic Tank
Cooling
None
Construction
Year Built
Year Built: 1970
Home type
Single Family Residence
Roof
Shingle
Construction Materials
Other
Architectural Style
Chalet
Property Condition
Existing
Foundation Details
Block
Utilities & Energy
Water Source
Drilled Well
Utilities
Other
Electric
Circuit Breakers
Other Features
Lot Features
Mountain View, Sloped
Price History
| Date | Event | Price |
|---|---|---|
10/28/2026 Source: | Listed for Sale | $559,000 -2.70% $315/sqft |
11/06/2025 Source: | Off Market | $574,500 $323/sqft |
11/05/2025 Source: | Price Decreased | $574,500 -1.71% $323/sqft |
10/30/2025 Source: | Price Decreased | $584,500 -2.57% $329/sqft |
10/22/2025 Source: | Price Decreased | $599,900 -6.98% $338/sqft |
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Based on information from PrimeMLS Inc. through Nov 02, 2026, 02:16PM. 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. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Nov 02, 2026, 02:16PM. © 2026 PrimeMLS, Inc. All Rights Reserved.
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