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Adam Dow

| The Dow Group | #1 Real Estate Team in New Hampshire

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99 Holly's Way , Rupert, VT 05776
$975,000
Est. Payment: $5,059.07/mo
3 Bed
2 Bath
2403 Sqft
Status: active | Days on site: 34
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VCR-C15903466 - VCR-C159091383,VCR-C159052275

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House 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.

Highlights

Listed by Derryl Lang , 802-733-6593 Four Seasons Sotheby's Int'l Realty , 802-362-4551. PrimeMLS mls logo

Property Type

Residential

Lot/Acreage
26

Year Built

1989

County

Bennington

School District

Bennington/Rutland

Listing ID

5094950

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Interior Features

Bedrooms and Bathrooms
  • Bedrooms:3
  • Bathrooms:2
  • Full Bathrooms:1
  • 3/4 Bathrooms:1
Appliances:Electric Cooktop, Dishwasher, Dryer, Freezer, Microwave, Wall Oven, Refrigerator, Washer, On Demand Water Heater
Air Cond:Mini Split
Fireplaces:
Floor:Carpet,Ceramic Tile,Wood
Above Ground Sq Ft:1652
Basement:Yes,Finished,Insulated,Storage Space,Interior Access,Exterior Access
Other:Level 1: Family Room,Level 1: Kitchen,Level 1: Living/Dining,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

Exterior Features

Lot:Existing
Zoning:Rural Residential
Roof:Standing Seam
Others:Deck,Garden Space,Outbuilding,Shed,Storage
Sewer:Leach Field,Septic
Parking Features:On-Site
Principal Interest
$5,059
Taxes
$837

Home Price

$975,000

Loan Details

30 yrs
6.75%

Down Payment

20%
$195,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$5,059.07

Principal

Taxes

Principal Taxes HOA Total
Monthly $5,059.07 $836.75 $0.00 $5,895.81
Yearly $60,708.78 $10,040.96 $0.00 $70,749.74
Total $1,821,263.46 $301,228.80 $0.00 $2,122,492.26

Today's Rates

30 Year

6.75%

20 Year

6.69%

15 Year

6.19%

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Market insight data is pulled from the same city as the listing being viewed (Rupert, VT).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

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 August 2, 2026 3:01am

Data last updated: 2026-08-02T07:01:24.600Z

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