Alison Day
REALTOR®
BEDS3
BATHS2 full
SQUARE FEET2,403
MLS#5094950
STATUSActive
PROPERTY TYPEResidential - Single Family
SCHOOLBennington-Rutland
Listing Courtesy of:
Four Seasons Sothebys Intl Realty
Agency Phone: 802-362-4551
Associate Name: Derryl Lang
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.
Property Features
Property Type: Residential - Single Family
Basement: Finished, Insulated, Storage Space, Interior Access, Exterior Access
Basement: Yes
Cooling: Mini Split
Garage: 1
Heating: Propane, Baseboard, Radiant Floor, Wood Furnace
Home Style: Contemporary
Lot Size: 26.00 Acres
Roof Type: Standing Seam
Stories: 1.5
Taxes: $10,040
Year Built: 1989
Amenities
Central 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
Deck
Garden Space
Outbuilding
Shed
Storage
Feature Descriptions
Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom, Access to Parking, Bathroom w/Step-in Shower, 1st Floor Laundry
Appliances: Electric Cooktop, Dishwasher, Dryer, Freezer, Microwave, Wall Oven, Refrigerator, Washer, On Demand Water Heater
Baths 3/4: 1
Baths Full: 1
Color: Grey
Construction: Metal Clad Exterior, Shingle Siding, Vinyl Exterior
Construction Status: Existing
Driveway: Circular, Gravel
Electric: On-Site, Underground
Equipment: Air Conditioner, Satellite Dish, Gas Stove, Portable Generator
Exterior: Metal Clad Exterior, Shingle Siding, Vinyl Exterior
Flood Zone: No
Flooring: Carpet, Ceramic Tile, Wood
Foundation: Concrete
Lot: Country Setting, Wooded, Rural
Number of Rooms: 8
Parking: On-Site
Road Frontage: 71
Roads: Association, Gravel, Shared, Privately Maintained
Sewer: Leach Field, Septic
Sq. Ft. Above Grade Finished: 1652
Sq. Ft. Below Grade Finished: 751
Sq. Ft. Total Finished: 2403
Total Stories: 1.5
Water: Drilled Well, Private
Zoning: Rural Residential
Room Sizes
Kitchen: 15 x 13.8 Level - 1
Living/Dining: 12.-2x23 Level - 1
Family Room: 31.-1x12.-8 Level - 1
Bedroom with Bath: 10.-9x12.-3 Level - 1
Bedroom: 18.-7x12.-3 Level - 2
Office/Study: 10.-8x12.-6 Level - 2
Bedroom: 22.-2x13.-4 Level - Basement
Bonus Room: 27x18.-2 Level - Basement
Local Schools
High School: Choice
Middle School: Choice
Elementary School: Mettawee Community School
School District: Bennington-Rutland
Listed By / Shown By
Listed By
Agency Name: Four Seasons Sothebys Intl Realty
Agent Name: Derryl Lang
Agency Phone: 802-362-4551
Shown By
Agent Name: Alison Day
Agent Phone: (800) 741-1540
Agency Title: Better Homes and Gardens Real Estate The Masiello Group
TOUR THIS HOME
Choose a date and time to see 99 Holly's Way, Rupert, VT 05776.
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Estimated Payment
$ 3,605.62 per month $2,448.12 Principal & Interest $836.67 Property Tax $320.83 Homeowner's Insurance
Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated 2026-06-15 23:33:03 
99 Holly's Way | MLS# 5094950
This single family home located at 99 Holly's Way, Rupert, VT 05776 is currently listed for sale with an asking price of $1,100,000. This property was built in 1989 and has 3 bedrooms and 2 full baths with 2403 sq. ft. Holly's Way is located within the Bennington-Rutland school district. Search Rupert real estate on alisonday.masiellogrouprealestate.com today.