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The standout homes of American ski country

41 Pleasant Street exterior
For sale
Photo: KW Vermont Woodstock
Woodstock, VT

41 Pleasant Street

Woodstock, VT · 05091

9 BD · 11 BA · 5,993 SQ FT

$2,599,000$434 / sq ft
Price / sq ft
$434
Year built
1899
Lot
0.46 acres
Days on market
377
Listed
September 21, 2025

Price and details as of October 3, 2026

Our takeBy Jack Beckett

A painted Victorian in Woodstock village, the only home in this group in the village itself. Built in 1899, it now runs as a seven-room inn with a two-bedroom owner's apartment, and the listing says it could be returned to a private home with a zoning permit.

The photos show a red-and-yellow house with a steep mansard roof, deep porches and a back deck in the trees. It asks $2.599 million for nearly 6,000 square feet, about $434 a foot. It has been on the market about 377 days.

41 Pleasant Street photo 2
41 Pleasant Street photo 3

“Quintessential New England living in a charming downtown setting.”

From the listing

From the listing

  • Victorian built in 1899 in Woodstock village
  • Currently a seven-room inn with owner's quarters
  • Could revert to a private home with a zoning permit, per the listing
  • Nine bedrooms and eleven baths in total
  • Covered porches and a rear deck
  • Walking distance to the village

Features as described by the listing brokerage. Ski Country Magazine has not independently verified them.

JF
Presented by
Jennifer Falvey
KW Vermont Woodstock

Listing details and photos provided by the listing brokerage via public listing data, and used with attribution. Figures current as of the last data pull.