Discover this quintessential Vermont ski chalet, perfectly set on a quiet dead-end road with views of Bromley Mountain from the property. Warm and inviting, the home is filled with natural wood throughout, creating the classic mountain-home atmosphere buyers love. Offering both charm and convenience, the location is ideal-just 2.5 miles to Bromley Mountain, 10 miles to Stratton, and only 8 miles to Manchester's restaurants, shops, indoor ice rink, and year-round amenities. Whether you're looking for a cozy retreat after a day on the slopes or a peaceful getaway surrounded by nature, this chalet delivers the perfect blend of privacy, comfort, and Vermont mountain living. Seasonal lease in place through April 19, 2026-buyer may close afterward or assume the lease with rental income prorated at transfer.

Listing Tools

More Info

Tax Information

  • Tax Year2025

Parking

  • Parking Spaces
  • GarageNo

Rooms

  • Full Bath1

Basic Information

  • MLS Number5070428
  • MLS StatusActive Under Contract
  • StatusActive With Contract
  • Property TypeSingle Family
  • List Price$359,000
  • Listing Agent NameCarrie Mathews
  • Broker NameWinhall Real Estate

Location

  • Building Number8
  • StreetWinhall Woods Road
  • TownWinhall
  • StateVT
  • Zip05340
  • CountyBennington
  • Elementary SchoolChoice
  • Junior HighChoice
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address8 Winhall Woods Road

Building

  • Year Built1963
  • Building ConstructionWood Frame
  • ConstructionExisting
  • Property StyleChalet
  • Bedrooms3
  • Bathroom2
  • Total Baths2
  • Half Bath1
  • Total Rooms7
  • Square Feet1,144
  • APX Unfin Below Grade676
  • BasementConcrete, Full
  • FoundationConcrete

Property

  • Acreage1.2
  • Lot DescriptionCountry Setting, Wooded, Near Skiing
  • AreaVT-Bennington
  • DrivewayGravel
  • RoadsPaved, Public Maintained Road

Interior

  • Interior FeaturesDining Area,1 Fireplace, Furnished, Kitchen/Dining, Natural Woodwork
  • FloorsCarpet, Manufactured, Wood
  • Stories2

Exterior

  • Exterior FeaturesBalcony, Porch
  • RoofMetal

Utilities

  • Heat SystemPropane, Forced Air
  • WaterDrilled Well
  • Sewer500 Gallon, Metal, Septic
  • ElectricCircuit Breaker(s)
  • UtilitiesCable

Amenities

  • Accessibility Amenities1st Floor Bedroom,1st Floor Full Bathroom
  • PricePerSqFt313.81

Other

  • SeasonalNo
  • Page348-351
  • Date Listed11/21/2025
  • View Count3

Map Location

Listed by Carrie Mathews of Winhall Real Estate
Broker Reciprocity 

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 February 14, 2026 8:22 PM EST

 

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