303 Winding Way

1,750 Sq. Ft.
$342 / Sq. Ft.
1,750
Sq. Ft.
$342
per Sq. Ft.

Description

Recent rehab, immaculately kept, fully furnished & ready to use for this season. Latest updates include hardwood flooring; kitchen w/stainless steel appliances; center island; super efficient HVAC system & hot water heater. Hot Springs hot tub on deck with gorgeous mountain views. Want some passive income to pay some of the bills? This property rents every time the owner makes it available. So you can close this week, leave your clothes & toothbrush & skis in a lockout closet & use it for available...Recent rehab, immaculately kept, fully furnished & ready to use for this season. Latest updates include hardwood flooring; kitchen w/stainless steel appliances; center island; super efficient HVAC system & hot water heater. Hot Springs hot tub on deck with gorgeous mountain views. Want some passive income to pay some of the bills? This property rents every time the owner makes it available. So you can close this week, leave your clothes & toothbrush & skis in a lockout closet & use it for available dates this season! Looking for a place to split with another family? Perfecto-mundo, with so much living/dining area! No need for the shades, total privacy & glorious sun & views. There is room next to dwelling to fit a garage or 'toy shed' for sleds, mountain bikes, etc. (see aerial plot plan in pictures)
  1. Listed by Robert Balewicz • Evergreen Realty of Vermont

Property Details for 303 Winding Way

Zoning
Residential
LISTING UPDATED: 01/17/2026 01:51 PM

Property Details for 303 Winding Way

StatusActive
MLS #5073999
Days on Market8
Taxes$1 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1970
Lot Size1.23 AC / 53,578 SF
CountyRutland County

Location

Listing Courtesy of Evergreen Realty of Vermont
Add your commute

Building Information for 303 Winding Way

Stories2Year Built1970Building Size-Lot Size1.23 AC / 53,578 SF

Payment Calculator

$2,920 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,919

Property Taxes

$0

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 303 Winding Way

Summary
Location and General Information
  • City: Killington
  • County: VT-Rutland
  • Directions: Route 100 to Doubleday Hill Road to left onto Winding Way, all the way to end, on left.
  • Latitude: 43.705583488255769
  • Longitude: -72.817682626983640
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Way
  • Zip Code: 05751
Taxes and HOA Information
  • SPAN Number: 58818510199
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Crushed Stone
Property
Lot Information
  • Lot Features: View, Wooded
  • Lot Size Acres: 1.23
  • Road Frontage Length: 200.0
Property and Assessments
  • Assessment Amount: $222,090
  • Assessment Year: 2024
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: No
  • Year Built: 1970
Utilities
  • Electric: 200+ Amp Service
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Propane
  • Internet: Cable Internet, DSL Available, Fiber Optic Internt Avail
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Siding
  • Roof: Asphalt Shingle
Interior Features
  • Appliances: Dishwasher, Dryer, Electric Range, Washer
  • Basement: No
  • Basement Description: Crawl Space
  • Flooring: Vinyl, Vinyl Plank
  • Heating: Baseboard, Hot Water
  • Cooling: None
  • Total Stories: 2
Rental
Rent Information
  • Rented: No

Property History for 303 Winding Way

DateEvent & SourcePriceAppreciation
Jan 14, 2026

Listed (Active)

New England Real Estate Network #5073999

$599,000—
Nov 16, 2025

Expired

New England Real Estate Network #5058022

—
Aug 24, 2025

Listed (Active)

New England Real Estate Network #5058022

$649,000—
Mar 4, 2025

Expired

New England Real Estate Network #5029563

—
Feb 25, 2025

Price Change

New England Real Estate Network #5029563

$459,900—
Feb 22, 2025

Price Change

New England Real Estate Network #5029563

$474,900—
Feb 17, 2025

Listed (Active)

New England Real Estate Network #5029563

$499,000—
Dec 24, 2024

Sold

New England Real Estate Network #5023127

$340,000—
Dec 24, 2024

Pending

New England Real Estate Network #5023127

—
Dec 23, 2024

Sold (Public Record)

Public Record #1548725133

$340,000—
Nov 28, 2024

Active Under Contract

New England Real Estate Network #5023127

—
Nov 25, 2024

Listed (Active)

New England Real Estate Network #5023127

$360,000—
Mar 19, 2017

Expired

New England Real Estate Network #4478746

—
Mar 28, 2016

Listed (Active)

New England Real Estate Network #4478746

$190,000—
Nov 30, 2014

Expired

New England Real Estate Network #4360870

—
Jun 3, 2014

Listed (Active)

New England Real Estate Network #4360870

$194,900—
Apr 30, 2014

Expired

New England Real Estate Network #4323292

—
Oct 28, 2013

Listed (Active)

New England Real Estate Network #4323292

$205,000—
Jul 2, 2013

Expired

New England Real Estate Network #4076565

—
Jul 2, 2011

Listed (Active)

New England Real Estate Network #4076565

$225,000—
Sep 27, 2010

Expired

New England Real Estate Network #3028760

—
Jan 1, 2009

Expired

New England Real Estate Network #2693798

—
Jun 30, 2008

Expired

New England Real Estate Network #273047

—
Dec 4, 2007

Listed (Active)

New England Real Estate Network #2693798

$319,000—
Jun 12, 2006

Listed (Active)

New England Real Estate Network #3028760

$389,000—
Jun 12, 2006

Listed (Active)

New England Real Estate Network #273047

$389,000—
DateEvent & SourcePrice
01/14/2026

Listed (Active)

New England Real Estate Network #5073999

$599,000
11/16/2025

Expired

New England Real Estate Network #5058022

—
08/24/2025

Listed (Active)

New England Real Estate Network #5058022

$649,000
03/04/2025

Expired

New England Real Estate Network #5029563

—
02/25/2025

Price Change

New England Real Estate Network #5029563

$459,900
02/22/2025

Price Change

New England Real Estate Network #5029563

$474,900
02/17/2025

Listed (Active)

New England Real Estate Network #5029563

$499,000
12/24/2024

Sold

New England Real Estate Network #5023127

$340,000
12/24/2024

Pending

New England Real Estate Network #5023127

—
12/23/2024

Sold (Public Record)

Public Record #1548725133

$340,000
11/28/2024

Active Under Contract

New England Real Estate Network #5023127

—
11/25/2024

Listed (Active)

New England Real Estate Network #5023127

$360,000
03/19/2017

Expired

New England Real Estate Network #4478746

—
03/28/2016

Listed (Active)

New England Real Estate Network #4478746

$190,000
11/30/2014

Expired

New England Real Estate Network #4360870

—
06/03/2014

Listed (Active)

New England Real Estate Network #4360870

$194,900
04/30/2014

Expired

New England Real Estate Network #4323292

—
10/28/2013

Listed (Active)

New England Real Estate Network #4323292

$205,000
07/02/2013

Expired

New England Real Estate Network #4076565

—
07/02/2011

Listed (Active)

New England Real Estate Network #4076565

$225,000
09/27/2010

Expired

New England Real Estate Network #3028760

—
01/01/2009

Expired

New England Real Estate Network #2693798

—
06/30/2008

Expired

New England Real Estate Network #273047

—
12/04/2007

Listed (Active)

New England Real Estate Network #2693798

$319,000
06/12/2006

Listed (Active)

New England Real Estate Network #3028760

$389,000
06/12/2006

Listed (Active)

New England Real Estate Network #273047

$389,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 303 Winding Way

Taxable ValueLand-Additions-Total-
Home Facts
Beds0Lot Size53,579 SqFtStyleSingle Family ResidenceCountyRUTLANDAPN(185) 10199

Schools near 303 Winding Way

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 12
Rating
School
Distance
Killington Elementary School
PublicPK to 6

Woodstock Senior Uhsd #4
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

303 Winding Way is a single family home for sale in Killington, VT 05751. This property was listed for sale on January 14, 2026 by Evergreen Realty of Vermont, it's currently listed at $599,000. It has been on the market for a total of 8 days and was last sold on December 24, 2024. This listing's school district is Windsor Central Unified Union School District. Nearby schools include Killington Elementary School and Woodstock Senior Uhsd #4. 303 Winding Way is a 4-bed, 3-bath, 1,750 sqft single family home built in 1970.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Evergreen Realty of Vermont

Copyright 2026 PrimeMLS, 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 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 01/22/2026 04:16 AM