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Single family home for sale at 303 Winding Way, Killington, VT 05751 | MLS# 5115977 | Listing updated on 2026-10-28
Photo 1 of Single family home for sale at 303 Winding Way, Killington, VT 05751 | MLS# 5115977 | Listing updated on 2026-10-28
Photo 2 of Single family home for sale at 303 Winding Way, Killington, VT 05751 | MLS# 5115977 | Listing updated on 2026-10-28
Photo 3 of Single family home for sale at 303 Winding Way, Killington, VT 05751 | MLS# 5115977 | Listing updated on 2026-10-28
Photo 4 of Single family home for sale at 303 Winding Way, Killington, VT 05751 | MLS# 5115977 | Listing updated on 2026-10-28
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Listed by: Nathan Mastroeni | Elevations Real Estate (802) 289-8463

$559,000

Monthly Est:$2,782

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon1,776sqft

303 Winding Way, Killington, VT 05751

$2,782/moEst:

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  • 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 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Rutland County

  • City

    Killington

  • 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

DateEventPrice

10/28/2026

Source: mls_logoNEREN/Prime MLS-NH #5115977

Listed for Sale

$559,000 -2.70%

$315/sqft

11/06/2025

Source: mls_logoNEREN/Prime MLS-NH #5058022

Off Market

$574,500

$323/sqft

11/05/2025

Source: mls_logoNEREN/Prime MLS-NH #5058022

Price Decreased

$574,500 -1.71%

$323/sqft

10/30/2025

Source: mls_logoNEREN/Prime MLS-NH #5058022

Price Decreased

$584,500 -2.57%

$329/sqft

10/22/2025

Source: mls_logoNEREN/Prime MLS-NH #5058022

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.

Advertising Broker: Derek Greene | The Greene Realty Group

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