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$800,000

3 Beds 2 Baths 2,403 SQFT 26.00 Acres
Type: Single Family

99 Holly's Way
Rupert, VT 05776

MLS#: 5094950
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649
Presented by: Derryl Lang with Four Seasons Sotheby's Int'l Realty;

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.


 

Interior Features

Bedrooms

Beds3

Other Interior Features

InternetHigh Speed Intrnt Avail
Total Finished Area2,403 sqft
Basement Access TypeWalkout
BasementYes
Basement DescriptionFinished, Insulated, Storage Space, Interior Access, Exterior Access
FlooringCarpet, Ceramic Tile, Wood
Interior AmenitiesCentral Vacuum, Blinds, Cathedral Ceiling, Dining Area, Gas Fireplace, Living/Dining, Primary BR w/ BA, Natural Light, Natural Woodwork, Vaulted Ceiling, Whirlpool Tub, 1st Floor Laundry

Other Rooms

Room 1 Level1
Rooms: Level BLevel B: Bedroom, Level B: Bonus Room
Rooms: Level 2Level 2: Bedroom, Level 2: Office/Study
Rooms: Level 1Level 1: Family Room, Level 1: Kitchen, Level 1: Living/Dining
Room 8 TypeBonus Room
Room 8 LevelBasement
Room 8 Dimensions27'x18'-2
Room 7 TypeBedroom
Room 7 LevelBasement
Room 7 Dimensions22'-2 x13'-4
Room 6 TypeOffice/Study
Room 6 Level2
Room 6 Dimensions10'-8 x12'-6
Room 5 TypeBedroom
Room 5 Level2
Room 5 Dimensions18'-7 x12'-3
Room 4 TypeBedroom with Bath
Room 4 Level1
Room 4 Dimensions10'-9 x12'-3
Room 3 TypeFamily Room
Room 3 Level1
Room 3 Dimensions31'-1 x12'-8
Room 2 TypeLiving/Dining
Room 2 Level1
Room 2 Dimensions12'-2 x23
Room 1 TypeKitchen
Room 1 Dimensions15' x 13'8
Total Rooms8

General

3/4 Baths1
Accessibility Features1st Floor Bedroom, 1st Floor Full Bathroom, Access to Parking, Bathroom w/Step-in Shower, 1st Floor Laundry
AppliancesElectric Cooktop, Dishwasher, Dryer, Freezer, Microwave, Wall Oven, Refrigerator, Washer, On Demand Water Heater
Bathrooms2
CityRupert
Construction MaterialsMetal Clad Exterior, Shingle Siding, Vinyl Exterior
CoolingMini Split
CovenantsUnknown
DOM97
DirectionsFrom Manchester, take Route 30 North, left on Route 315 to Rupert, turn right on Route 153 North. Drive 3.9 miles, turn left onto Holly's Way. Turn left at stone wall (with light) at next fork, take the
ElectricOn-Site, Underground
Electric CompanyGreen Mountain Power
Elementary SchoolMettawee Community School
ExclusionsPersonal items
Flood ZoneNo
Fuel CompanySams Fuel
Full Baths1
GarageYes
Half Baths0
HeatingPropane, Baseboard, Radiant Floor, Wood Furnace
High SchoolChoice
Last Updated09/21/2026 18:49:06
Middle SchoolChoice
Other EquipmentAir Conditioner, Satellite Dish, Gas Stove, Portable Generator
Price Per Sq Ft Total AG$484
Property ClassResidential
Property ConditionExisting
Road FrontageYes
RoofStanding Seam
School DistrictBennington/Rutland
SeasonalNo
SewerLeach Field, Septic
Status Detail0
Stories Count1.5
StyleContemporary
Tax Year2026
TypeSingle Family
UtilitiesPropane, Telephone at Site, Underground Utilities
Year Built1989
ZoningRural Residential

Exterior

ColorGrey
DrivewayCircular, Gravel
Exterior AmenitiesDeck, Garden Space, Outbuilding, Shed, Storage
Foundation Concrete
Garage Capacity1
Lot FeaturesCountry Setting, Wooded, Rural
Lot Size Area26 sqft
Lot Size Square Feet1132560
Parking FeaturesOn-Site
Road Frontage Length71 sqft
Road Frontage TypeAssociation, Gravel, Shared, Privately Maintained
SurveyedYes
Water SourceDrilled Well, Private

Additional Details

Price History

Schools 

Middle School Choice Middle School
High School Choice High School
Elementary School Mettawee Community School Elementary School

  

Similar Properties

$800,000

3 Beds 2 Baths 2,403 SQFT 26.00 Acres
Type: Single Family

99 Holly's Way
Rupert, VT 05776

MLS#: 5094950
Chris Bernier
Chris Bernier
Churchill Properties
Principal Broker/Owner
Phone: 978.578.5013
Office: 833.668.4649