For Sale
Single family home for sale at 99 Holly'S Wy, West Pawlet, VT 05775 | MLS# 5094950 | Listing updated on 2026-10-06
Photo 1 of Single family home for sale at 99 Holly'S Wy, West Pawlet, VT 05775 | MLS# 5094950 | Listing updated on 2026-10-06
Photo 2 of Single family home for sale at 99 Holly'S Wy, West Pawlet, VT 05775 | MLS# 5094950 | Listing updated on 2026-10-06
Photo 3 of Single family home for sale at 99 Holly'S Wy, West Pawlet, VT 05775 | MLS# 5094950 | Listing updated on 2026-10-06
Photo 4 of Single family home for sale at 99 Holly'S Wy, West Pawlet, VT 05775 | MLS# 5094950 | Listing updated on 2026-10-06
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Listed by: Derryl Lang | Four Seasons Sotheby's Int'l Realty (802) 362-4551

$800,000

Monthly Est:$3,982

  • Beds Icon3 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,652sqft

99 Holly'S Wy, West Pawlet, VT 05775

$3,982/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1989

  • $-- HOA

  • 26 acres lot

  • $484/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: October 6, 2026 at 1:24 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5094950 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Bennington County

  • City

    West Pawlet

  • Neighborhood

    --

  • Year Built

    1989

  • HOA Fees

    -

  • Finished Area

    1,652 sqft

  • Lot Size

    26 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5094950

  • MLS Status

    (10) Active - Active

  • Days on Market

    139

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 2

Interior

  • Interior Features

    Central Vacuum, Blinds, Cathedral Ceiling(s), Dining Area, Gas Fireplace, Living/dining, Primary Br W/ Ba, Natural Light, Natural Woodwork, Vaulted Ceiling(s), Whirlpool Tub, 1st Floor Laundry

  • Exterior Features

    Deck, Garden, Outbuilding, Shed, Storage

  • Appliances

    Electric Cooktop, Dishwasher, Dryer, Freezer, Microwave, Wall Oven, Refrigerator, Washer, On Demand Water Heater

  • Heating

    Propane, Baseboard, Radiant Floor, Wood Furnace

  • Sewer

    Leach Field, Septic Tank

  • Cooling

    Mini Split

  • Flooring

    Ceramic Tile, Carpet, Wood

Construction

  • Year Built

    Year Built: 1989

  • Home type

    Single Family Residence

  • Roof

    Standing Seam

  • Construction Materials

    Metal Clad Exterior, Shingle Siding, Vinyl Exterior

  • Foundation Details

    Concrete

  • Architectural Style

    Contemporary

  • Property Condition

    Existing

Utilities & Energy

  • Electric

    On Site, Underground

  • Basement

    Finished, Insulated, Storage Space, Interior Entry, Exterior Entry

  • Water Source

    Drilled Well, Private

  • Parking Features

    On Site

  • Utilities

    Propane, Phone Connected, Underground Utilities

Other Features

  • Lot Features

    Country Setting, Wooded, Rural

Price History

DateEventPrice

09/20/2026

Source: mls_logoNEREN/Prime MLS-NH #5094950

Price Decreased

$800,000 -13.51%

$484/sqft

09/01/2026

Source: mls_logoNEREN/Prime MLS-NH #5094950

Price Decreased

$925,000 -5.13%

$560/sqft

07/19/2026

Source: mls_logoNEREN/Prime MLS-NH #5094950

Listed for Sale

$975,000

$590/sqft

Nearby Homes

Based on information from PrimeMLS Inc. through Nov 02, 2026, 02:16PM. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of PrimeMLS. 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 Nov 02, 2026, 02:16PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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