- beds
- —
- baths
- —
- sq ft
- —
- Built
- 1899
41 Pleasant Street
Woodstock, VT 05091
Commercial Sale · Active · MLS #5056243
Listing Courtesy of KW Vermont Woodstock | Jennifer Falvey, Steven Foster
The home
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 information
Details at a glance
Interior1 property facts
- Heating
- Zoned
Building3 property facts
- Style
- Other
- Year built
- 1899
- Roof
- Metal
Land & utilities3 property facts
- Lot size
- 0.46 acres
- Water
- Public
- Sewer
- Public Sewer
Financial2 property facts
- Annual taxes
- $33,925
- Assessment year
- 2025
Plan your purchase
Estimated monthly cost
Explore costs at the $2,599,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$15,969 / monthAdjust
- Principal & interest
- $13,142
- Property tax
- $2,827
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $33,925. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
Listing history
Price and status timeline
- New
$2,599,000 · Sep 21, 2025
Compare with confidence
Price & market context
See how this home compares with active listings in Woodstock.
| Metric | This home | Local listings |
|---|---|---|
| List price | $2,599,000 | $1,122,500132% above local |
| Price / sq ft | — | — |
| Days on market | 139 | 40248% above local |
Active city listing statistics from PrimeMLS as of September 12, 2026. Asking prices are not completed-sale values.
Keep exploring
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Need help making sense of this home?
Common questions
About 41 Pleasant Street
Can I request a private showing?
Request a tour of 41 Pleasant Street and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
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