99 Hollys Way
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...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.
- Listed by Derryl Lang • Four Seasons Sotheby's Int'l Realty
Property Details for 99 Hollys Way
Zoning
Rural Residential
LISTING UPDATED: 06/16/2026 02:39 PM
Property Details for 99 Hollys Way
| Status | Active |
|---|---|
| MLS # | 5094950 |
| Days on Market | 11 |
| Taxes | $10,041 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Residential / Single Family |
| Year Built | 1989 |
| Lot Size | 26.00 AC / 1,132,560 SF |
| County | Bennington County |
Location
Listing Courtesy of Four Seasons Sotheby's Int'l Realty
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Building Information for 99 Hollys Way
Stories1Year Built1989Building Size-Lot Size26.00 AC / 1,132,560 SF
Payment Calculator
$6,318 per month
30 year fixed, 6.36% Interest
Principal and Interest
$5,481
Property Taxes
$837
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 99 Hollys Way
Summary
Location and General Information
- City: Rupert
- County: VT-Bennington
- 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 left dirt drive (sort of middle as well) proceed up and around, house will come into view first.
- Latitude: 43.309305000001004
- Longitude: -73.246047000000004
- Road Frontage: Yes
- Seasonal: No
- State: VT
- Street Designation: Way
- Zip Code: 05776
Taxes and HOA Information
- SPAN Number: 537-16910116
- Tax Year: 2026
- Taxes TBD: No
Parking
- Garage: Yes
- Garage Capacity: 1.00
- Driveway: Circular, Gravel
Property
Lot Information
- Lot Features: Country Setting, Wooded, Rural
- Lot Size Acres: 26.0
- Road Frontage Length: 71.0
- Total Finished Area: 2403.0
- Above Grade Finished Area: 1652.0
- Above Grade Finished Area Source: Plans
- Above Grade Unfinished Area: 0.0
- AboveGradeUnfinishedAreaSource: Plans
- Below Grade Finished Area: 751.0
- Below Grade Finished Area Source: Plans
- Below Grade Unfinished Area: 390.0
- BelowGradeUnfinishedAreaSource: Plans
- Lot Size Square Feet: 1132560.0
- Total Area: 2793.0
Property and Assessments
- Current Use: Yes
- Property Class: Residential
- Property Type: Single Family
- Construction Status: Existing
- Flood Zone: No
- Owned Land: Yes
- PreConstruction: No
- Surveyed: Yes
- Year Built: 1989
- School District: Bennington/Rutland
- High School: Choice
- Middle/Jr School: Choice
- Elementary School: Mettawee Community School
Utilities
- Electric Company: Green Mountain Power
- Fuel Company: Sams Fuel
- Electric: On-Site, Underground
- Sewer: Leach Field, Septic
- Water Source: Drilled Well, Private
- Utilities: Propane, Telephone at Site, Underground Utilities
- Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
- Color: Grey
- Construction Materials: Metal Clad Exterior, Shingle Siding, Vinyl Exterior
- Roof: Standing Seam
Interior Features
- Appliances: Electric Cooktop, Dishwasher, Dryer, Freezer, Microwave, Wall Oven, Refrigerator, Washer, On Demand Water Heater
- Basement: Yes
- Basement Access Type: Walkout
- Basement Description: Finished, Insulated, Storage Space, Interior Access, Exterior Access
- Rooms: Level 1: Level 1: Family Room, Level 1: Kitchen, Level 1: Living/Dining
- Rooms: Level 2: Level 2: Bedroom, Level 2: Office/Study
- Rooms: Level B: Level B: Bedroom, Level B: Bonus Room
- Flooring: Carpet, Ceramic Tile, Wood
- Heating: Propane, Baseboard, Radiant Floor, Wood Furnace
- Cooling: Mini Split
- Total Stories: 1.5
- Rooms Total: 8
- Bathrooms Full: 1
- Bathrooms Half: 0
- Bathrooms One Quarter: 0
- Bathrooms Three Quarter: 1
- Bedrooms Total: 3
- Bathrooms Total: 2
Room Information
Room 1
- Room Dimensions: 15' x 13'8"
- Room Level: 1
- Room Type: Kitchen
Room 2
- Room Dimensions: 12'-2"x23"
- Room Level: 1
- Room Type: Living/Dining
Room 3
- Room Dimensions: 31'-1"x12'-8"
- Room Level: 1
- Room Type: Family Room
Room 4
- Room Dimensions: 10'-9"x12'-3"
- Room Level: 1
- Room Type: Bedroom with Bath
Room 5
- Room Dimensions: 18'-7"x12'-3"
- Room Level: 2
- Room Type: Bedroom
Room 6
- Room Dimensions: 10'-8"x12'-6"
- Room Level: 2
- Room Type: Office/Study
Room 7
- Room Dimensions: 22'-2"x13'-4"
- Room Level: Basement
- Room Type: Bedroom
Room 8
- Room Dimensions: 27'x18'-2"
- Room Level: Basement
- Room Type: Bonus Room
Property History for 99 Hollys Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Jun 16, 2026 | Listed (Active) New England Real Estate Network #5094950 | $1,100,000 | — |
| May 9, 2003 | Sold (Public Record) Public Record #547329167 | $210,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 06/16/2026 | Listed (Active) New England Real Estate Network #5094950 | $1,100,000 |
| 05/09/2003 | Sold (Public Record) Public Record #547329167 | $210,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 99 Hollys Way
Taxable ValueLand$158,100Additions$318,900Total$477,000
Home Facts
Beds0Lot Size3,815,856 SqFtStyleSingle Family ResidenceCountyBENNINGTONAPN(169)10116
Schools near 99 Hollys Way
This home is within Mettawee School District.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 6 |
Rating | School | Distance |
|---|---|---|
Mettawee Community School Usd #47 PublicPK to 6 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Four Seasons Sotheby's Int'l Realty
Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 06/28/2026 12:47 AM
