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99 Holly's Way, 
Rupert, VT 05776

$1,100,000


3

Beds


2

Baths


2,403

Sq Ft


Single Family

Active

Listed by

Derryl Lang

Four Seasons Sotheby'S Int'L Realty

802-362-4551

Last updated:

July 11, 2026, 03:28 PM

MLS#

5094950

Source:

PrimeMLS

About This Home

99 Holly's Way

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.

Home Facts

Single Family

2 Baths

3 Bedrooms

Built in 1989

Price Summary

1,100,000

$457 per Sq. Ft.

MLS #:

5094950

Last Updated:

July 11, 2026, 03:28 PM

Added:

25 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

1

Interior

Living Area:

2,403 Sq. Ft.


Structure

Structure

Building Area:

2,793 Sq. Ft.

Year Built:

1989


Lot

Lot Size (Sq. Ft):

1,132,560


Finances & Disclosures

Finances

Price:

$1,100,000

Price per Sq. Ft:

$457 per Sq. Ft.

MLS Logo
Copyright 2026 Prime MLS, 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 Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 11, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.