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99 Holly's Way

rupert, VT 05776

$1,100,000

  • 3 BR
    2 BA

Interested? Let's Connect

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.

Details

26 Private Acres Lot Size

single family home

Built in 1989

MLS/Listing ID 5094950

Amenities & Features

Construction - Shingle Siding

Style - Contemporary

Washer

Refrigerator

Wall Oven

Microwave

Freezer

Dryer

Dishwasher

Electric Cooktop

Heating - Propane

Natural Wood

Carpet

Construction - Vinyl Siding

Deck

Garden

Shed

Parking - On Site

Lot - Rural

Lot - Wooded

Vaulted Ceilings

Natural Woodwork

Dining Area

Cathedral Ceilings

Central Vacuum

Heating - Radiant Floor

Heating - Baseboard

Ceramic Tile

Storage

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

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