41 Pleasant Street, Woodstock, VT 05091

Woodstock
Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
41 Pleasant Street,Woodstock, VT 05091
$2,599,000
  • 9 Beds
  • 11 Baths
  • 5,993 sq. ft.
  • Single family
  • Active
Listed by: jennifer falvey, steven fosterCell: 203-912-8173
Office: kw vermont woodstock802-654-8500
MLS#:5062350
Source:PrimeMLS

Price summary

  • Price:$2,599,000
  • Price per sq. ft.:$304.3

About this home

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in 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 offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner’s quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home!

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Home facts

  • Year built:1899
  • Listing ID #:5062350
  • Added:381 day(s) ago
  • Updated:October 08, 2026 at 11:26 AM

Rooms and interior

  • Bedrooms:9
  • Total bathrooms:11
  • Full bathrooms:11
  • Rooms Total:16
  • Flooring:Carpet, Manufactured, Tile, Wood
  • Kitchen Description:Dishwasher, Microwave, Refrigerator
  • Basement Description:Interior, Storage Space, Unfinished
  • Living area:5,993 sq. ft.

Heating and cooling

  • Cooling:Wall AC
  • Heating:Oil

Structure and exterior

  • Roof:Metal, Standing Seam
  • Year built:1899
  • Building area:5,993 sq. ft.
  • Lot area:0.46 Acres
  • Levels:2.5 Story

Schools

  • High school:Woodstock Senior UHSD #4
  • Middle school:Woodstock Union Middle Sch
  • Elementary school:Woodstock Elementary School

Utilities

  • Sewer:Public Available

Finances and disclosures

  • Price:$2,599,000
  • Price per sq. ft.:$304.3
  • Tax amount:$33,925 (2025)

Features and amenities

  • Appliances:Refrigerator, Washer
  • Laundry features:Dryer, Washer

Parking

  • Parking description:Paved Driveway
MLS LogoCopyright 2026 Prime MLS, Inc. 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 Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 8, 2026

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