List Price: $1,100,000 | $666 per sq.ft. | 3 Bedroom | 2 Bathroom | 1.5 Story Single Family Home
Date Listed Tuesday Jun 16, 2026 | MLS# 5094950
Date Listed Tuesday Jun 16, 2026 | MLS# 5094950
To see this Listing
Address: 99 Holly's Way Rupert VT
Listed by Derryl Lang Four Seasons Sotheby's Int'l Realty
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.
Listed by Derryl Lang Four Seasons Sotheby's Int'l Realty
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.
Room Information:
Total Rooms: 8
Total Baths: 2
Flooring: Carpet | Ceramic Tile | Wood
Full Baths: 1
3/4 Baths: 1
Bedrooms: 3
Kitchen size: 15' x 13'8"
Total Baths: 2
Flooring: Carpet | Ceramic Tile | Wood
Full Baths: 1
3/4 Baths: 1
Bedrooms: 3
Kitchen size: 15' x 13'8"
Basement: Finished | Insulated | Storage Space | Interior Access | Exterior Access
Construction Information:
Year Built: 1989
Type: Metal Clad Exterior | Shingle Siding | Vinyl Exterior
Type: Metal Clad Exterior | Shingle Siding | Vinyl Exterior
Building Info
Finished Sq.Ft.: 2793
Above Grade Sq.Ft.: 1652
Below Grade Sq.Ft.: 751
Apx Below Grade Unfinished Sq.Ft.: 390
Exterior Info
Style: Contemporary
Exterior Color Grey
Roof: Standing Seam
Utilities
Electric: On-Site | Underground
Water: Drilled Well | Private
Sewer: Leach Field | Septic
Land Description:
Country Setting | Wooded | Rural
Lot size: 26 acres
Zoned: Rural Residential
Surveyed: Yes
SurveyedBy: Action Surveyin
Flood Zone: No
Seasonal: No
Road Frontage: 71
Driveway: Circular | Gravel
Additional Information
Taxes $10,041
Assesed Value Not Reported
Taxes $10,041
Assesed Value Not Reported
Schools
School District: Bennington/Rutland
Elementary School: Mettawee Community School
Middle School: Choice
High School: Choice
School District: Bennington/Rutland
Elementary School: Mettawee Community School
Middle School: Choice
High School: Choice
