99 Holly's WAY, Rupert, VT 05776
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99 Holly's WAY, Rupert, VT 05776
99 Holly's WAY, Rupert, VT 05776
99 Holly's WAY, Rupert, VT 05776
99 Holly's WAY, Rupert, VT 05776
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Vermont Real Estate Company

Vermont Real Estate Company

+1(802) 540-8300
Listed by Derryl Lang • Four Seasons Sotheby's Int'l Realty
$ 1,100,000
Est. payment /mo
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99 Holly's WAY Rupert, VT 05776

3 Beds

2 Baths

2,403 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family

Listing Status Active

Purchase Type For Sale

Square Footage 2,403 sqft

Price per Sqft $457

MLS Listing ID 5094950

Style Contemporary

Bedrooms 3

Full Baths 1

Three Quarter Bath 1

Construction Status Existing

Year Built 1989

Annual Tax Amount $10,040

Tax Year 2026

Lot Size 26.000 Acres

Acres 26.0

Property Sub-Type Single Family

Property Description

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.

Location

State VT

County Vt-bennington

Area Vt-Bennington

Zoning Rural Residential

Rooms

Basement Entrance Walkout

Basement Finished, Insulated, Storage Space, Interior Access, Exterior Access

Interior

Heating Propane, Baseboard, Radiant Floor, Wood Furnace

Cooling Mini Split

Flooring Carpet, Ceramic Tile, Wood

Exterior

Parking Features Yes

Garage Spaces 1.0

Utilities Available Propane, Telephone at Site, Underground Utilities

Roof Type Standing Seam

Building

Lot Description Country Setting, Wooded, Rural

Story 1.5

Sewer Leach Field, Septic

Water Drilled Well, Private

Architectural Style Contemporary

Construction Status Existing

Schools

Elementary Schools Mettawee Community School

Middle Schools Choice

High Schools Choice

School District Bennington/Rutland

PrimeMLS

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99 Holly's WAY

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