41 Pleasant St

Woodstock, VT 05091

$2,599,000
Price
9
Beds
5,993 Sq. Ft.
$434 / Sq. Ft.
5,993
Sq. Ft.
$434
per Sq. Ft.

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...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!
  1. Listed by Jennifer Falvey • KW Vermont Woodstock • Cell: 203-912-8173
  2. Listed by Steven Foster • KW Vermont-Stowe

Property Details for 41 Pleasant Street

Zoning
Non-residential
LISTING UPDATED: 02/07/2026 08:00 PM

Property Details for 41 Pleasant Street

StatusActive
MLS #5062350
Days on Market112
Taxes$33,925 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1899
Lot Size0.46 AC / 20,037 SF
CountyWindsor County

Location

Listing Courtesy of KW Vermont Woodstock; KW Vermont-Stowe
Add your commute

Building Information for 41 Pleasant Street

Stories2Year Built1899Building Size-Lot Size0.46 AC / 20,037 SF

Payment Calculator

$15,494 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,667

Property Taxes

$2,827

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 41 Pleasant Street

Summary
Location and General Information
  • City: Woodstock
  • County: VT-Windsor
  • Directions: Head West on Route 4. 41 Pleasant St is .2 miles past Maplefields on the left.
  • Latitude: 43.626516467809651
  • Longitude: -72.511246830688478
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05091
Taxes and HOA Information
  • SPAN Number: 786-250-10177
  • Tax Year: 2025
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Paved
Property
Lot Information
  • Lot Features: Landscaped, Level, Sidewalks, In Town, Near Paths, Near Shopping, Neighborhood, Near Public Transportatn
  • Lot Size Acres: 0.46
  • Road Frontage Length: 114.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • Owned Land: Yes
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1899
Utilities
  • Electric: 200+ Amp Service
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable Available, Telephone Available
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: Pink
  • Construction Materials: Post and Beam, Wood Frame
  • Roof: Metal, Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Gas Range, Refrigerator, Washer, Gas Stove, Water Heater
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Storage Space, Unfinished
  • Flooring: Carpet, Manufactured, Tile, Wood
  • Heating: Propane, Oil
  • Cooling: Wall AC Units
  • Total Stories: 2.5

Property History for 41 Pleasant Street

DateEvent & SourcePriceAppreciation
Sep 21, 2025

Listed (Active)

New England Real Estate Network #5062350

$2,599,000—
Jan 28, 2021

Sold (Public Record)

Public Record #688370322

$1,550,000

+4.0% / yr

Jan 27, 2021

Sold

New England Real Estate Network #4809479

$1,550,000—
Dec 12, 2020

Pending

New England Real Estate Network #4809479

—
Jun 6, 2020

Price Change

New England Real Estate Network #4809479

$1,750,000—
Jun 6, 2020

Listed (Active)

New England Real Estate Network #4809479

$1,700,000—
Jul 5, 2018

Sold (Public Record)

Public Record #625354508

$1,400,000—
DateEvent & SourcePrice
09/21/2025

Listed (Active)

New England Real Estate Network #5062350

$2,599,000
01/28/2021

Sold (Public Record)

Public Record #688370322

$1,550,000

+4.0% / yr

01/27/2021

Sold

New England Real Estate Network #4809479

$1,550,000
12/12/2020

Pending

New England Real Estate Network #4809479

—
06/06/2020

Price Change

New England Real Estate Network #4809479

$1,750,000
06/06/2020

Listed (Active)

New England Real Estate Network #4809479

$1,700,000
07/05/2018

Sold (Public Record)

Public Record #625354508

$1,400,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 41 Pleasant Street

Taxable ValueLand$246,000Additions$870,300Total$1,116,300
Tax Record2022$29,053 ($2,421 / month)
Home Facts
Total Finished SqFt5,993 SqFtAbove Grade Finished SqFt5,993 SqFtLot Size20,038 SqFtStyleHotel / MotelYear Built1899CountyWINDSORAPN(250) 21.52.18Fireplace TypeHas Fireplace

Schools near 41 Pleasant Street

This home is within Windsor Central Unified Union School District.
Rating
School
Type
Grades
Distance
Woodstock Elementary School
Public - PK to 4
Woodstock Senior Uhsd #4
Public - 7 to 12
Rating
School
Distance
Woodstock Elementary School
PublicPK to 4

Woodstock Senior Uhsd #4
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 41 Pleasant Street, Woodstock, VT 05091

41 Pleasant Street is a single family home for sale in Woodstock, VT 05091. This property was listed for sale on September 21, 2025 by KW Vermont Woodstock, it's currently listed at $2,599,000. It has been on the market for a total of 112 days and was last sold on January 28, 2021. This listing's school district is Windsor Central Unified Union School District. Nearby schools include Woodstock Elementary School and Woodstock Senior Uhsd #4. 41 Pleasant Street is a 9-bed, 11-bath, 5,993 sqft single family home built in 1899.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of KW Vermont Woodstock; KW Vermont-Stowe

Copyright 2026 PrimeMLS, 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 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 02/21/2026 07:10 AM