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Courtesy of Jennifer Falvey of KW Vermont Woodstock: Cell: 203-912-8173.

41 Pleasant Street

Woodstock, VT 05091
  • $2,599,000
  • STATUS: Active
  • MLS #: 5062350
UPDATED: 101 min ago
$2,599,000
  • 9
    BEDS
  • 0.46
    ACRES
  • 11
    BATHS
  • 0
    1/2 BATHS
  • 5,993
    SQFT
  • $434
    $/SQFT
Type:
Single-Family Home
Built:
1899
County:
Area:

School Information

Elementary School:
School District:

Description

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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© 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 2026-06-12T00:05:48.827.
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41 Pleasant Street Woodstock, VT 05091

  • Price: $2,599,000
  • Status: Active
  • On Site: Days
  • Updated: 101 min ago
  • MLS #: 5062350
9
Beds
11
Baths
0
½ Baths
0.46
Acres
5,993
SQFT
$434
$/SQFT
1899
Built
County:
Windsor
Area:
Woodstock
Elementary School:
Woodstock Elementary School
Middle School:
Woodstock Union Middle Sch
High School:
Woodstock Senior Uhsd #4
School District:
Woodstock Uhsd 4
Property Description
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!
Exterior Features

Architectural Style Victorian Color Pink Construction Materials Post and BeamWood Frame Driveway Paved Exterior Features BalconyGarden SpaceNatural ShadePatioCovered Porch Has Garage No Lot Features LandscapedLevelSidewalksIn TownNear PathsNear ShoppingNeighborhoodNear Public Transportatn Owned Land Yes Parking On-SiteParking Spaces 1 - 10 Road Frontage Yes Road Frontage Length 114 Roof MetalStanding Seam

Interior Features

Appliances DishwasherDryerRange HoodMicrowaveElectric RangeGas RangeRefrigeratorWasherGas StoveWater Heater Basement Access Type Interior Basement Description Storage SpaceUnfinished Cooling Wall AC Units Flooring CarpetManufacturedTileWood Foundation BrickConcrete Has Basement Yes Heating PropaneOil Interior Features BarCeiling FanDining AreaGas Fireplace1 FireplaceIn-Law/Accessory DwellingPrimary BR w/ BANatural WoodworkSecurityWalk-in ClosetWet BarWhirlpool Tub1st Floor Laundry Quarter Baths 0 Rooms Total 16 Sq Ft Approx Fin Above Grade 5993 Sq Ft Approx Fin Below Grade 0

Property Features

Auction No Construction Status Existing Covenants Unknown Electric 200+ Amp Service Flood Zone No Foreclosed / Bank Owned / REO No Pre Construction No Property Type Single Family Road Frontage Type PavedPublic Seasonal No Sewer Public Span Number 786-250-10177 Surveyed Unknown Tax Gross Amount 33925.46 Tax Year 2025 Taxes Tbd No Timeshare Fractional Own No Utilities Cable AvailableTelephone Available Water Source Public Zoning Non-residential

Courtesy of Jennifer Falvey of KW Vermont Woodstock: Cell: 203-912-8173.


© 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 2026-06-12T00:05:48.827.
 
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