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Listed by: KW Vermont Woodstock • Jennifer Falvey

$2,599,000

41 Pleasant Street, Woodstock, VT 05091

9beds

5,993sqft

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Single Family Residence

Built in 1899

0.46 Acres Lot

$2,439,000 Zestimate^®

$434/sqft

$-- HOA

What's special

Stately homesMaple-lined streets

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!

295 days

508

31

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Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 9
Bathrooms: 11
Full bathrooms: 11

Heating

Propane, Oil

Cooling

Wall Unit(s)

Appliances

Included: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Gas Range, Refrigerator, Washer, Gas Stove, Water Heater
Laundry: 1st Floor Laundry

Features

Bar, Ceiling Fan(s), Dining Area, Primary BR w/ BA, Natural Woodwork, Walk-In Closet(s), Wet Bar
Flooring: Carpet, Manufactured, Tile, Wood
Basement: Storage Space,Unfinished,Interior Entry
Number of fireplaces: 1
Fireplace features: Gas, 1 Fireplace

Interior area

Total structure area: 8,541
Total interior livable area: 5,993 sqft
Finished area above ground: 5,993
Finished area below ground: 0

Property

Parking

Parking features: Paved, On Site, Parking Spaces 1 - 10

Features

Levels: 2.5
Stories: 2.5
Patio & porch: Patio, Covered Porch
Exterior features: Balcony, Garden, Natural Shade
Has spa: Yes
Spa features: Bath
Frontage length: Road frontage: 114

Lot

Size: 0.46 Acres
Features: Landscaped, Level, Sidewalks, In Town, Near Paths, Near Shopping, Neighborhood

Details

Parcel number: 78625010177
Zoning description: Non-residential
Other equipment: Sprinkler System

Construction

Type & style

Home type: SingleFamily
Architectural style: Victorian
Property subtype: Single Family Residence

Materials

Post and Beam, Wood Frame
Foundation: Brick, Concrete
Roof: Metal,Standing Seam

Condition

New construction: No
Year built: 1899

Utilities & green energy

Electric: 200+ Amp Service
Sewer: Public Sewer
Utilities for property: Cable Available, Phone Available

Community & HOA

Community

Security: Security, Carbon Monoxide Detector(s), Security System, Smoke Detector(s)

Location

Region: Woodstock

Financial & listing details

Price per square foot: $434/sqft
Tax assessed value: $1,116,300
Annual tax amount: $33,925
Date on market: 9/21/2025
Road surface type: Paved

Estimated market value

$2,439,000

$2.32M - $2.56M

$3,353/mo

Price history

Date	Event	Price
9/21/2025	Listed for sale	$2,599,000+67.7%$434/sqft
Source: PrimeMLS #5062350 Report a problem
1/27/2021	Sold	$1,550,000-8.8%$259/sqft
Source: PrimeMLS #4809479 Report a problem
12/12/2020	Pending sale	$1,700,000$284/sqft
Source: PrimeMLS #4809479 Report a problem
8/11/2020	Price change	$1,700,000-2.9%$284/sqft
Source: High End Realty #4809479 Report a problem
6/6/2020	Listed for sale	$1,750,000+311.4%$292/sqft
Source: High End Realty #4809479 Report a problem
8/29/2001	Sold	$425,400$71/sqft
Source: Public Record Report a problem

Public tax history

Year	Property taxes	Tax assessment
2024	--	$1,116,300
2023	--	$1,116,300
2022	--	$1,116,300
2021	--	$1,116,300 +51.7%
2020	--	$735,700
2019	--	$735,700
2018	--	$735,700
2017	--	$735,700
2016	--	$735,700 +8685.5%
2015	--	$8,374
2014	--	$8,374
2013	--	$8,374
2012	--	$8,374
2011	--	$8,374

Find assessor info on the county website

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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

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