41 Pleasant Street Woodstock, Vermont - For Sale

41 Pleasant Street Woodstock, Vermont 05091 MLS# 5062350

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For Sale Status

$2,599,000 List Price

House Type

9 Beds

11 Baths

5,993 Sqft

Listed By Jennifer Falvey of KW Vermont Woodstock - Cell: 203-912-8173
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41 Pleasant Street
Village Inn of Woodstock, VT Village Inn of Woodstock, VT
Village Inn of Woodstock, VT Village Inn of Woodstock, VT
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
Front porch Front porch
41 Pleasant Street
Dining on the terrace. Dining on the terrace.
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
Second floor landing Second floor landing
41 Pleasant Street
The Tavern The Tavern
41 Pleasant Street
41 Pleasant Street
Commercial kitchen Commercial kitchen
41 Pleasant Street
41 Pleasant Street
Front dining room Front dining room
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
Back dining room Back dining room
Stairs to second floor Stairs to second floor
41 Pleasant Street
41 Pleasant Street
Guest room Guest room
Guest room Guest room
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
Guest suite with balcony Guest suite with balcony
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street
Coffee room on third floor Coffee room on third floor
Owners' quarters Owners' quarters
Living room in owners' quarters Living room in owners' quarters
41 Pleasant Street
Kitchen in owners' quarters Kitchen in owners' quarters
41 Pleasant Street
41 Pleasant Street
First foor bedroom in owners' quarters with ensuite bathroom First foor bedroom in owners' quarters with ensuite bathroom
First floor bath in owners' quarters First floor bath in owners' quarters
Primary bedroom in owners' quarters Primary bedroom in owners' quarters
41 Pleasant Street
Primary bath in owners' quarters Primary bath in owners' quarters
41 Pleasant Street
41 Pleasant Street
41 Pleasant Street

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!

Property Location

41 Pleasant Street Woodstock

Property Details

List Price  $2,599,000 Total Rooms  16 List Date  Sep 21st, 2025
Cooperation Fee  Unknown Lot Size  0.46 Acres Taxes $33,925
MLS#  5062350 Days on Market  271 Days Tax Year 2025
Type  House Stories  2 1/2 Road Frontage  114
Bedrooms  9 Style  Victorian Water Frontage  
Full Bathrooms  11 Finished  5,993 Sqft Construction  No, Existing
3/4 Bathrooms  0 Above Grade  5,993 Sqft Seasonal  No
Half Bathrooms  0 Below Grade  0 Sqft Year Built  1899
1/4 Bathrooms  0 Garage Size   Car County  Windsor
Interior Features
Equipment & AppliancesDishwasher, Dryer, Washer, Refrigerator, Microwave, Gas Range, Refrigerator, Washer, Gas Stove, Water Heater
ConstructionPost and Beam, Wood Frame
BasementStorage Space, Unfinished
Exterior Features
Disability Features
Foundation   House Color  Pink
Floors  Carpet,Manufactured,Tile,Wood Building Certifications  
Roof  Standing Seam, Metal HERS Index  
DirectionsHead West on Route 4. 41 Pleasant St is .2 miles past Maplefields on the left.
Lot DescriptionLandscaped, Level, Sidewalks, In Town, Near Paths, Near Shopping, Neighborhood, Near Public Transportatn
Garage & Parking  
Road Frontage Type  Paved,Public Water Access  
Suitable Use Water Type  
Driveway  Paved Water Body  
Flood Zone  No Zoning  Non-residential
School District  Woodstock UHSD 4 Middle  Woodstock Union Middle Sch
Elementary  Woodstock Elementary School High  Woodstock Senior UHSD #4
Heating  Propane, Oil Items Excluded  
Cooling  Wall AC Units Negotiable  
Sewer  Public Parcel Access ROW  
Water  Public ROW for Other Parcel  
Water Heater   Financing  
Cable Co   Documents  
Electric  200+ Amp Service Tax ID  786-250-10177
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† The remarks published on this webpage originate from Listed By Jennifer Falvey of KW Vermont Woodstock - Cell: 203-912-8173 via the PrimeMLS IDX Program and do not represent the views and opinions of Coldwell Banker Hickok & Boardman. Coldwell Banker Hickok & Boardman cannot be held responsible for possible violations of copyright resulting from the posting of any data from the PrimeMLS IDX Program.