Map
USAVTWest Rupert99 Hollys Way
Listing image | Image 1

99 Hollys Way, West Rupert, VT

House

For Sale

Listed price in listed location currency (USD).
$975,000

321

MLS® 5094950

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 2403 sqft
Garage Yes
Taxes $10,041
Days Active 41
Lot Size 26 Acres
Approx. Age 1989
Avg. Price Per Sqft $405
MLS® Number 5094950

Property Address: 99 Hollys Way, West Rupert, VT, 05776

Average square foot calculated using Size range provided by listing agent.

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.
MLS® Number5094950
Laundry Level
Central VacNo
FireplaceNo
Acreage
Exterior
GarageYes
Approx. Age1989
BasementExterior Access, Finished, Insulated, Interior Access, Storage Space
DrivewayOn Site
Garage Spaces
HeatPropane, Baseboard, Radiant Floor, Wood Furnace
A/CMini Split

Extras

Rooms

Change to metres

Family Room:First Floor12.67 × 31.09 ft
Kitchen:First Floor13.67 × 15 ft
Bathroom 1:First Floor12.25 × 10.75 ft
Bedroom 1:Second Floor12.25 × 18.59 ft
Bonus Room:Basement18.17 × 27 ft
Bedroom 2:Basement13.34 × 22.17 ft
Other:First Floor23 × 12.17 ft
Office:Second Floor12.5 × 10.67 ft

Price History

-End Date
Not Sold YetSold Price

For Sale

Jun 16, 2026List Date
$975,000List Price
  • Commute

Commute

Starting Address
Destination Address
99 Hollys Way, West Rupert, VT

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