List Price: $975,000 | $590 per sq.ft. | 3 Bedroom | 2 Bathroom | 1.5 Story Single Family Home
Price Change! Reduced by $125,000 down 13% on July 20th 2026

Listed Tuesday Jun 16, 2026 | MLS# 5094950
99 Holly's Way Rupert VT
Listed by Derryl Lang Four Seasons Sotheby's Int'l Realty
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.

Appliances : Electric Cooktop | Dishwasher | Dryer | Freezer | Microwave | Wall Oven | Refrigerator | Washer | On Demand Water Heater
Flooring: Carpet | Ceramic Tile | Wood
Heating: Propane | Baseboard | Radiant Floor | Wood Furnace
Total Rooms: 8
Total Baths: 2
Full Baths: 1
3/4 Baths: 1
Total Bedrooms: 3
Kitchen: Room Dimensions: 15' x 13'8" Floor: 1
Living/Dining : Room Dimensions: 12'-2"x23" Floor: 1
Family Room : Room Dimensions: 31'-1"x12'-8" Floor: 1
Bedroom with Bath : Room Dimensions: 10'-9"x12'-3" Floor: 1
Bedroom : Room Dimensions: 18'-7"x12'-3" Floor: 2
Office/Study : Room Dimensions: 10'-8"x12'-6" Floor: 2
Bedroom : Room Dimensions: 22'-2"x13'-4" Floor: Basement
Bonus Room : Room Dimensions: 27'x18'-2" Floor: Basement

Building Info
Year Built: 1989
Type: Metal Clad Exterior | Shingle Siding | Vinyl Exterior
Total Structure SqFt.: 2793
Finished Sqft. Above Ground: 1652
Below Ground SqFt.: 751
Apx Below Grade Unfinished SqFt.: 390
Basement: Finished | Insulated | Storage Space | Interior Access | Exterior Access

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



Taxes $10,041
Assesed Value Not Reported
Schools
School District: Bennington/Rutland
Elementary School: Mettawee Community School
Middle School: Choice
High School: Choice

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