41 Pleasant Street
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The tavern is straight ahead, and the dining rooms are to the right.
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Dining room with view onto the terrace.
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55 photos

$2,599,000

41 Pleasant Street
Woodstock, VT 05091
Listed by Jennifer Falvey · KW Vermont Woodstock
Bedrooms
N/A
Bathrooms
N/A
Living area
N/A
Year built
1899

About this home

This exquisite 8-room Inn which boasts an additional 1-bedroom owner’s quarters, invites you to embrace the quintessential New England bed and breakfast owner’s dream. The Village Inn of Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities throughout the year. Guests from all over the world return to the Village Inn year after year to enjoy its charming rooms, cozy tavern and amazing restaurant. This Inn is a well-oiled machine with very impressive revenue growth. Call for more information and a chance to tour this property.

Property details

MLS #
5056243
Property type
Commercial Sale
Subdivision
N/A
Status
Active
Days on market
325
On market date
N/A
Stories
N/A
Garage spaces
N/A
Lot size
0.46 acres
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Est. monthly payment
$15,801/mo
$519,800 down
$2,079,200 loan
Principal & interest$13,486
Property tax (est.)$2,166
Home insurance (est.)$150

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Copyright 2026 PrimeMLS. 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 02/07/26.