109 Winhall Hollow RoadWinhall, VT 05340MLS Number 5081867

  • Price: $1,200,000
  • Est. Mortgage of $/month
  • 49 Days on Market
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%
$/month over payments
Federal 30-year interest rate: 6.36% last updated on May 14, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340109 Winhall Hollow Road Winhall VT 05340
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  • 23.5Acreage
  • 1Bathrooms
  • 2020Year Built
  • 950Square Feet

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Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a homeit is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling that masterfully blends industrial strength with warm, natural aesthetics. Its bold, dark-bronze standing seam metal exterior provides a sleek, low-maintenance finish that stands out against the lush Vermont landscape. The upper-level living space features a massive wall of glass that opens onto a spacious deck, offering a one-of-a-kind vantage point to enjoy your morning coffee while scouting the ski conditions across the valley. Complementing the living quarters, the ground floor offers high-clearance multi-functional space, perfect for a professional-grade workshop, gear room, or housing a full fleet of UTVs and mountain bikes. Beyond the residence, the land has been transformed into a premier recreational paradise. You can navigate professionally designed and carved mountain bike trails that wind through the expansive 23.5-acre forest. Below the main house, a vast, rolling meadow leads to a custom stone firepit areathe ultimate destination for aprs-bike gatherings under the stars. Located just minutes from Stratton Mountain Resort, this estate offers a rare combination of architectural sophistication and private access to the best of the Vermont outdoors. This property is also primed for future expansion and the creation of a grander mountain estate. The septic system was specifically built to accommodate a new five-bedroom house, and comprehensive plans are available for viewing for the proposed home. Representing the very best of the Vermont lifestyle, this offering provides both a turnkey adventure hub and a ready-to-build canvas for your dream residence.
Listed by Margaret McMahon of Four Seasons Sotheby's Int'l Realty

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Tax Information

  • Tax Year2026

Location

  • Building Number109
  • StreetWinhall Hollow Road
  • TownWinhall
  • StateVT
  • Zip05340
  • CountyBennington
  • DistrictChoice
  • Elementary SchoolChoice
  • Junior HighChoice
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address109 Winhall Hollow Road

Exterior

  • Exterior ColorBrown
  • RoofMetal

Amenities

  • PricePerSqFt1263.16

Parking

  • Parking Spaces1
  • GarageYes

Building

  • Year Built2020
  • Building ConstructionWood Frame
  • ConstructionExisting
  • Property StyleContemporary
  • Bathroom1
  • Total Baths1
  • 3/4 Baths1
  • Total Rooms4
  • Square Feet950
  • FoundationConcrete

Interior

  • Room 1 TypeBathroom Three Quarter
  • Room 1 Level2
  • Room 2 TypeMudroom
  • Room 2 Level1
  • Room 3 TypeKitchen/Living
  • Room 3 Level2
  • Room 4 TypeLoft
  • Room 4 Level3
  • Stories2.5

Basic Information

  • MLS Number5081867
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$1,200,000
  • Listing Agent NameMargaret McMahon
  • Broker NameFour Seasons Sotheby's Int'l Realty

Property

  • Acreage23.5
  • Lot DescriptionMountain View, Wooded
  • AreaVT-Bennington
  • DrivewayGravel
  • RoadsPublic

Utilities

  • Heat SystemRadiant Floor
  • WaterDrilled Well
  • SewerSeptic
  • ElectricUnderground
  • UtilitiesCable Available

Other

  • SeasonalNo
  • Page752-754
  • Date Listed04/02/2026
  • View Count6
Bellville Realty
Bellville Realty
Office: 802-257-7979
16 Harmony Place
Brattleboro, VT 05301
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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 May 20, 2026 5:09 PM EDT

 

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