For Sale
Single family home for sale at 159 Winhall Hollow Rd, Bondville, VT 05340 | MLS# 5104104 | Listing updated on 2026-08-08
Photo 1 of Single family home for sale at 159 Winhall Hollow Rd, Bondville, VT 05340 | MLS# 5104104 | Listing updated on 2026-08-08
Photo 2 of Single family home for sale at 159 Winhall Hollow Rd, Bondville, VT 05340 | MLS# 5104104 | Listing updated on 2026-08-08
Photo 3 of Single family home for sale at 159 Winhall Hollow Rd, Bondville, VT 05340 | MLS# 5104104 | Listing updated on 2026-08-08
Photo 4 of Single family home for sale at 159 Winhall Hollow Rd, Bondville, VT 05340 | MLS# 5104104 | Listing updated on 2026-08-08
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Listed by: Kim Morgan-Wohler | Wohler Realty Group (802) 297-3333

$5,575,000

Monthly Est:$27,749

  • Beds Icon7 Beds
  • Beds Icon
    10 Baths
  • Beds Icon7,423sqft

159 Winhall Hollow Rd, Bondville, VT 05340

$27,749/moEst:

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  • Single Family Residence

  • Built in 2002

  • $-- HOA

  • 42.93 acres lot

  • $751/sq.ft

Description

Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 7,423 SF residence itself and massive barn. There's an immediate sense of permanence here.Thoughtfully positioned for complete privacy, the 7 ensuite Bedroom/9.5 bath home possesses the scale, presence, & quiet grandeur reminiscent of New England's great legacy estates. Its architecture feels substantial yet entirely at home within its surroundings, balancing stately proportions and refined craftsmanship with the warmth and authenticity of a distinguished country property. Expansive lawns, pastoral vistas, mature trees, and distant mountain views create a magnificent natural setting on 42.93 acres, while the home stands as its centerpiece: elegant and enduring.The Main Residence features multiple gathering spaces, three fireplaces, beautiful wood floors, impeccable stonework, fine woodworking and upscale details. It's grand in scale, warm in spirit, and created for gathering. Meticulously crafted stone archways, wood beams and oversized timber mantels frame the hearths. A generous chef’s kitchen with premier appliances and custom design was conceived for those who appreciate the art of cooking and the pleasure of company. An extraordinary barn enhances the property with it's interior grand lodge room framed with reclaimed barn beams, a 2 story stone hearth, ideal for entertaining and apres ski fun, guest quarters with kitchen and 3 bay garage.This represents Vermont country living at its most distinguished a rare convergence of masterful craftsmanship, remarkable acreage, architectural character, and an incomparable natural setting. It's a home for generations to gather. Just 5 minutes to the Stratton Mountain Access Road,20 min to Manchester

  • Houzeo last checked: 12 hours ago
  • Listing updated: August 8, 2026 at 9:34 pm
  • Source: NEREN/Prime MLS-NH | MLS#: 5104104 NEREN/Prime MLS-NH

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Vt Bennington County

  • City

    Bondville

  • Neighborhood

    --

  • Year Built

    2002

  • HOA Fees

    -

  • Finished Area

    7,423 sqft

  • Lot Size

    42.93 acres lot

  • Basement Area

    - sqft

  • MLS Name

    NEREN/Prime MLS

  • MLS Number

    5104104

  • MLS Status

    (10) Active - Active

  • Days on Market

    62

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 7

    Bathrooms: 10

Interior

  • Sewer

    1000 Gallon, Septic Tank

  • Cooling

    Central Air

  • Heating

    Propane, Baseboard, Hot Water

Construction

  • Year Built

    Year Built: 2002

  • Home type

    Single Family Residence

  • Foundation Details

    Concrete

  • Roof

    Asphalt Shingle

  • Property Condition

    Existing

  • Architectural Style

    Freestanding, Multi Level, New Englander, Tri Level

  • Construction Materials

    Wood Frame, Wood

Utilities & Energy

  • Utilities

    Cable, Phone Connected

  • Electric

    Underground

  • Basement

    Concrete, Concrete Floor, Full, Storage Space, Unfinished

  • Water Source

    Drilled Well

Other Features

  • Lot Features

    Country Setting, Pasture, Landscaped, Level, Mountain View, Open Lot, Other, Secluded, Views, Walking Trails, Wooded, Mountain, Near Skiing, Private

Price History

DateEventPrice

08/08/2026

Source: mls_logoNEREN/Prime MLS-NH #5104104

Listed for Sale

$5,575,000

$751/sqft

Nearby Homes

Based on information from PrimeMLS Inc. through Oct 09, 2026, 02:32PM. 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 Oct 09, 2026, 02:32PM. © 2026 PrimeMLS, Inc. All Rights Reserved.

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