159 Winhall Hollow RoadWinhall, VT 05340MLS Number 5104104

  • Price: $5,575,000
  • Est. Mortgage of $/month
  • 2 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.69% last updated on Aug 6, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340159 Winhall Hollow Road Winhall VT 05340
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  • 7Bedrooms
  • 42.93Acreage
  • 10Bathrooms
  • 2002Year Built

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Listed by Kim Morgan-Wohler of Wohler Realty Group
Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 7,423 SF residence itself and massive barn. There's an immediate sense of permanence here.Thoughtfully positioned for complete privacy, the 7 ensuite Bedroom/9.5 bath home possesses the scale, presence, & quiet grandeur reminiscent of New England's great legacy estates. Its architecture feels substantial yet entirely at home within its surroundings, balancing stately proportions and refined craftsmanship with the warmth and authenticity of a distinguished country property. Expansive lawns, pastoral vistas, mature trees, and distant mountain views create a magnificent natural setting on 42.93 acres, while the home stands as its centerpiece: elegant and enduring.The Main Residence features multiple gathering spaces, three fireplaces, beautiful wood floors, impeccable stonework, fine woodworking and upscale details. It's grand in scale, warm in spirit, and created for gathering. Meticulously crafted stone archways, wood beams and oversized timber mantels frame the hearths. A generous chef's kitchen with premier appliances and custom design was conceived for those who appreciate the art of cooking and the pleasure of company. An extraordinary barn enhances the property with it's interior grand lodge room framed with reclaimed barn beams, a 2 story stone hearth, ideal for entertaining and apres ski fun, guest quarters with kitchen and 3 bay garage.This represents Vermont country living at its most distinguished a rare convergence of masterful craftsmanship, remarkable acreage, architectural character, and an incomparable natural setting. It's a home for generations to gather. Just 5 minutes to the Stratton Mountain Access Road,20 min to Manchester

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More Info

Tax Information

  • Tax Year2025

Location

  • Building Number159
  • StreetWinhall Hollow Road
  • TownWinhall
  • StateVT
  • Zip05340
  • CountyBennington
  • DistrictChoice
  • Elementary SchoolChoice
  • Junior HighChoice
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address159 Winhall Hollow Road

Interior

  • Stories3

Exterior

  • RoofAsphalt Shingle

Utilities

  • Heat SystemPropane, Baseboard, Hot Water
  • WaterDrilled Well
  • Sewer1000 Gallon, Septic
  • ElectricUnderground
  • UtilitiesCable, Telephone at Site

Parking

  • Parking Spaces5
  • GarageYes

Building

  • Year Built2002
  • Building ConstructionWood Frame, Wood Exterior
  • ConstructionExisting
  • Property StyleFreestanding, Multi-Level, New Englander, Tri-Level
  • Bedrooms7
  • Bathroom10
  • Total Baths10
  • Half Bath1
  • Total Rooms18
  • Square Feet7,423
  • APX Unfin Below Grade3097
  • BasementConcrete, Concrete Floor, Full, Storage Space, Unfinished
  • FoundationConcrete

Amenities

  • PricePerSqFt751.04

Other

  • SeasonalNo
  • Page465
  • Date Listed08/08/2026

Rooms

  • Full Bath9

Basic Information

  • MLS Number5104104
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$5,575,000
  • Listing Agent NameKim Morgan-Wohler
  • Broker NameWohler Realty Group

Property

  • Acreage42.93
  • Lot DescriptionCountry Setting, Field/Pasture, Landscaped, Level, Mountain View, Open, Other, Secluded, View, Walking Trails, Wooded, Mountain, Near Skiing, Private
  • AreaVT-Bennington
  • DrivewayGravel
  • RoadsPublic Maintained Road
  • Road Frontage2034
Dave Chenette | Chenette Real Estate
Dave Chenette | Chenette Real Estate
Office: 802-264-1991
9 Roberts Ct
Milton, VT 05468
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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 August 9, 2026 8:53 AM UTC

 

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