Coldwell Banker Home Page

Local Realty Service Provided By: Coldwell Banker Lifestyles

Property view
Listing view 2
Listing view 3

303 Winding Way, 
Killington, VT 05751

$559,000


4

Beds


3

Baths


1,776

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Nathan Mastroeni

Elevations Real Estate

802-289-8463

Last updated:

November 1, 2026, 04:08 PM

MLS#

5115977

Source:

PrimeMLS

About This Home

303 Winding Way

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.

Home Facts

Single Family

3 Baths

4 Bedrooms

Built in 1970

Price Summary

559,000

$314 per Sq. Ft.

MLS #:

5115977

Last Updated:

November 1, 2026, 04:08 PM

Added:

5 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,776 Sq. Ft.


Structure

Structure

Building Area:

1,776 Sq. Ft.

Year Built:

1970


Lot

Lot Size (Sq. Ft):

53,579


Finances & Disclosures

Finances

Price:

$559,000

Price per Sq. Ft:

$314 per Sq. Ft.

MLS Logo
Copyright 2026 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated November 2, 2026

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.

Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.