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Imagine waking to the quiet rhythm of the Vermont countryside, where morning light stretches across open meadows, woodland trails begin just beyond your door, and the pace of life slows to match the landscape. Set on 26 acres in Rupert, this exceptional property offers a rare combination of privacy, craftsmanship, and room to pursue the life you've imagined. The home is designed to feel connected to its surroundings, with warm wood finishes, expansive windows, and comfortable living spaces that invite both gathering and relaxation. Throughout the property, extraordinary stonework, all from the quarry on-site, reflects a level of artistry and care rarely found today. Beyond the home, a fully equipped 3,100-square-foot heated garage and workshop creates endless possibilities. Featuring radiant heat, a commercial-grade car lift, office space, bathroom, heat pumps, central vacuum, air lines, and oversized 12' x 12' doors, it is an ideal setting for automotive enthusiasts, collectors, entrepreneurs, craftspeople, or anyone seeking exceptional workspace. The land itself is a destination. Explore private trails through mature woods, enjoy open fields, snowshoe after a fresh snowfall, or take advantage of the nearby D&H Rail Trail. Every season brings new opportunities to experience the beauty of Vermont. Additional storage buildings provide ample space for equipment, recreational gear, and the practical needs of country living. Both the home and workshop benefit from updated high-efficiency heating systems for year-round comfort. Conveniently located within easy reach of Manchester, Dorset, regional ski areas, and the Adirondacks, this property offers the perfect balance of seclusion and accessibility. Whether you're seeking a full-time residence, a weekend retreat, a live-work property, or a place to gather family and friends for years to come, this Rupert estate offers a lifestyle defined by space, creativity, and connection to the land. Schedule your private tour today.

More Info

Tax Information

  • Tax Year2026

Location

  • Building Number99
  • StreetHolly's Way
  • TownRupert
  • StateVT
  • Zip05776
  • CountyBennington
  • DistrictBennington/Rutland
  • Elementary SchoolMettawee Community School
  • Junior HighChoice
  • High SchoolChoice
  • Flood Zone Y/NNo
  • Address99 Holly's Way

Interior

  • Interior FeaturesCentral Vacuum, Blinds, Cathedral Ceiling, Dining Area, Gas Fireplace, Living/Dining, Primary BR w/ BA, Natural Light, Natural Woodwork, Vaulted Ceiling, Whirlpool Tub,1st Floor Laundry
  • Room 1 TypeKitchen
  • Room 1 Level1
  • Room 1 Dimensions15' x 13'8"
  • FloorsCarpet, Ceramic Tile, Wood
  • Room 2 TypeLiving/Dining
  • Room 2 Level1
  • Room 2 Dimensions12'-2"x23"
  • Room 3 TypeFamily Room
  • Room 3 Level1
  • Room 3 Dimensions31'-1"x12'-8"
  • Room 4 TypeBedroom with Bath
  • Room 4 Level1
  • Room 4 Dimensions10'-9"x12'-3"
  • Room 5 TypeBedroom
  • Room 5 Level2
  • Room 5 Dimensions18'-7"x12'-3"
  • Stories1.5
  • Room 6 TypeOffice/Study
  • Room 6 Level2
  • Room 6 Dimensions10'-8"x12'-6"
  • Room 7 TypeBedroom
  • Room 7 LevelBasement
  • Room 7 Dimensions22'-2"x13'-4"
  • Room 8 TypeBonus Room
  • Room 8 LevelBasement
  • Room 8 Dimensions27'x18'-2"

Parking

  • Parking Spaces1
  • GarageYes
  • Parking DescriptionOn-Site

Building

  • Year Built1989
  • Building ConstructionMetal Clad Exterior, Shingle Siding, Vinyl Exterior
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms3
  • Bathroom2
  • Total Baths2
  • 3/4 Baths1
  • Total Rooms8
  • Square Feet2,403
  • APX Unfin Below Grade390
  • BasementFinished, Insulated, Storage Space, Interior Access, Exterior Access
  • FoundationConcrete

Utilities

  • Heat SystemPropane, Baseboard, Radiant Floor, Wood Furnace
  • WaterDrilled Well, Private
  • SewerLeach Field, Septic
  • ElectricOn-Site, Underground
  • UtilitiesPropane, Telephone at Site, Underground Utilities

Rooms

  • Full Bath1

Basic Information

  • MLS Number5094950
  • MLS StatusActive
  • StatusACT
  • Property TypeSingle Family
  • List Price$1,100,000
  • Listing Agent NameDerryl Lang
  • Broker NameFour Seasons Sotheby's Int'l Realty

Property

  • Acreage26
  • Lot DescriptionCountry Setting, Wooded, Rural
  • AreaVT-Bennington
  • DrivewayCircular, Gravel
  • RoadsAssociation, Gravel, Shared, Privately Maintained
  • Road Frontage71

Exterior

  • Exterior FeaturesDeck, Garden Space, Outbuilding, Shed, Storage
  • Exterior ColorGrey
  • RoofStanding Seam

Amenities

  • Accessibility Amenities1st Floor Bedroom,1st Floor Full Bathroom, Access to Parking, Bathroom w/Step-in Shower,1st Floor Laundry
  • AmenitiesAir Conditioner, Satellite Dish, Gas Stove, Portable Generator
  • PricePerSqFt665.86

Other

  • SeasonalNo
  • Page396
  • Date Listed06/16/2026

Map Location

Driving Directions

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 June 17, 2026 7:09 AM UTC

 

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