Price Reduction
Address
99 Holly's Way, Rupert, VT
Price
$ 925,000
Property Attributes
- MLS#5094950
- TypeSingle Family
- Listing Status Active
- CountyBENNINGTON
- CityRupert
- AreaBennington
- Zip05776
- StyleContemporary
- Year Built1989
- Price$ 925,000
- Bedrooms3
- Full Bathrooms2
- Half Bathrooms0
- Sqr Footage2403
- Lot Size26 Acres
Data Source:
PrimeMLS
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.
| Elementary School | Middle School | High School |
|---|---|---|
| Mettawee Community School Elementary School | Choice Middle School | Choice High School |
| Price History | |
|---|---|
| 6/16/2026 | Listed $1,100,000 |
| 7/20/2026 | 12$975,000 |
| 9/2/2026 | 6$925,000 |
General Features
| Road Frontage | Yes |
|---|---|
| Sewer | Leach Field,Septic |
| Heating | Propane,Baseboard,Radiant Floor,Wood Furnace |
| Cooling | Mini Split |
| Utilities | Propane,Telephone at Site,Underground Utilities |
| Roof | Standing Seam |
| Appliances | Electric Cooktop,Dishwasher,Dryer,Freezer,Microwave,Wall Oven,Refrigerator,Washer,On Demand Water Heater |
| Garage | Yes |
| Flood Zone | No |
| Zoning | Rural Residential |
| Exclusions | Personal items |
| 3/4 Baths | 1 |
| Full Baths | 1 |
| Bathrooms | 2 |
| Year Built | 1989 |
| Electric | On-Site,Underground |
| Style | Contemporary |
| Stories Count | 1.5 |
| Type | Single Family |
| Property Condition | Existing |
| Accessibility Features | 1st Floor Bedroom,1st Floor Full Bathroom,Access to Parking,Bathroom w/Step-in Shower,1st Floor Laundry |
| Tax Year | 2026 |
| Fuel Company | Sams Fuel |
| Electric Company | Green Mountain Power |
| Covenants | Unknown |
| Construction Materials | Metal Clad Exterior,Shingle Siding,Vinyl Exterior |
| Directions | From 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 |
| High School | Choice |
| City | Rupert |
| Property Class | Residential |
| Other Equipment | Air Conditioner,Satellite Dish,Gas Stove,Portable Generator |
| School District | Bennington/Rutland |
| Seasonal | No |
| Elementary School | Mettawee Community School |
| Middle School | Choice |
| DOM | 79 |
| Price Per Sq Ft Total AG | 559.93 |
| Last Updated | 09/02/2026 20:47:15 |
Interior Features
| Basement Description | Finished,Insulated,Storage Space,Interior Access,Exterior Access |
|---|---|
| Interior 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 |
| Basement | Yes |
| Flooring | Carpet,Ceramic Tile,Wood |
| Beds | 3 |
| Total Rooms | 8 |
| Room 1 Level | 1 |
| Internet | High Speed Intrnt Avail |
| Total Finished Area | 2403 |
| Rooms: Level B | Level B: Bedroom,Level B: Bonus Room |
| Rooms: Level 2 | Level 2: Bedroom,Level 2: Office/Study |
| Rooms: Level 1 | Level 1: Family Room,Level 1: Kitchen,Level 1: Living/Dining |
| Room 8 Type | Bonus Room |
| Room 8 Level | Basement |
| Room 8 Dimensions | 27'x18'-2 |
| Room 7 Type | Bedroom |
| Room 7 Level | Basement |
| Room 7 Dimensions | 22'-2 x13'-4 |
| Room 6 Type | Office/Study |
| Room 6 Level | 2 |
| Room 6 Dimensions | 10'-8 x12'-6 |
| Room 5 Type | Bedroom |
| Room 5 Level | 2 |
| Room 5 Dimensions | 18'-7 x12'-3 |
| Room 4 Type | Bedroom with Bath |
| Room 4 Level | 1 |
| Room 4 Dimensions | 10'-9 x12'-3 |
| Room 3 Type | Family Room |
| Room 3 Level | 1 |
| Room 3 Dimensions | 31'-1 x12'-8 |
| Room 2 Type | Living/Dining |
| Room 2 Level | 1 |
| Room 2 Dimensions | 12'-2 x23 |
| Room 1 Type | Kitchen |
| Room 1 Dimensions | 15' x 13'8 |
| Basement Access Type | Walkout |
Exterior Features
| Lot Features | Country Setting,Wooded,Rural |
|---|---|
| Exterior Amenities | Deck,Garden Space,Outbuilding,Shed,Storage |
| Driveway | Circular,Gravel |
| Lot Size Area | 26 |
| Water Source | Drilled Well,Private |
| Parking Features | On-Site |
| Garage Capacity | 1 |
| Foundation | Concrete |
| Color | Grey |
| Road Frontage Length | 71 |
| Road Frontage Type | Association,Gravel,Shared,Privately Maintained |
| Surveyed | Yes |
| Lot Size Square Feet | 1132560 |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 05776
Statistics provided by Inside Real Estate
Price
Year Built
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not be used for any purpose other than to identify prospective properties
consumers may be interested in purchasing. Data last updated September 10, 2026 4:47 AM UTC
