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303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo
303 Winding Way, Killington, VT 05751 Photo

34 Total Photos [Click to View All]

  • Listing Provided by:
    Elevations Real Estate
    Phone: 802-289-8463
    Agent: Nathan Mastroeni IDX logo

  • 4
    Beds
  • 3
    Baths
  • 1,776
    Square Feet
  • 5115977
    MLS#
$544,000
Status: Active
303 Winding Way Killington, VT 05751

Property 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.

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Property Features

MLS Number: 5115977
Subdivision:
County: Rutland
Bedrooms: 4
Full Baths: 2
3/4 Baths: 1
Total Square Feet: 1,776
Style: Chalet
New Constuction: No
Construction: Other
Outdoor Features: Deck, Hot Tub
Waterfront: No
Property Type: Residential - Single Family
Cooling: None
Heating: Propane, Baseboard
Lot Size: 1.23 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $5,886
Year Built: 1970

Amenities

Natural Light
Deck
Hot Tub

Feature Descriptions

Appliances: Dryer, Microwave, Refrigerator, Washer, Gas Stove
Baths 3/4: 1
Baths Full: 2
Color: brown
Construction: Other
Days on Market: 17
Driveway: Gravel
Electric: Circuit Breaker(s)
Exterior: Other
Flood Zone: No
Flooring: Carpet
Foundation: Block
Home Style: Chalet
Hot Tub: Yes
Lot: Mountain View, Sloping
Number of Rooms: 5
Roads: Public Maintained Road
Sewer: Septic
Sq. Ft. Above Grade Finished: 1776
Sq. Ft. Total Finished: 1776
Total Stories: 2
Water: Drilled Well
Zoning: residential

Location

Listed By / Shown By

Listed By

Broker Name: Elevations Real Estate
Agent Name: Nathan Mastroeni
Broker Phone: 802-289-8463

agent picture

Shown By

Agent Name: Keegan Rice
Agent Phone: Cell: (603) 348-7261
Broker Title: Badger Peabody & Smith Realty

IDX logo

Estimate Your Payment

Estimated Payment

$ 3,579.72 per month $2,930.55 Principal & Interest $490.50 Property Tax $158.67 Homeowner's Insurance

Source: Delta Media Group, Inc.

Change Payment Information

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 11/14/2026. The listing information on this page last changed on 11/14/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 11/14/2026 8:18:26 AM EST) or Prime MLS (last updated Fri 11/13/2026 2:36:24 PM EST) or MREIS (last updated Sat 11/14/2026 7:22:10 AM EST). Real estate listings held by brokerage firms other than Badger Peabody & Smith Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) 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 2026-11-13 14:36:24

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