Sign up to get new listings emailed daily! JOIN SIGN IN
Crystal Athas
REALTOR®
VCard Icon 

41 Pleasant Street, Woodstock, VT 05091

$2,599,000
  • Main Photo

55 Total Photos [Click to View All]

Active
BEDS9 BATHS11 full SQUARE FEET5,993 MLS#5062350
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWoodstock UHSD 4

Listing Courtesy of: KW Vermont Woodstock
Agency Contact: Cell: 203-912-8173
Associate Name: Jennifer Falvey
IDX logo


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!

41 Pleasant Street | MLS# 5062350

This single family home located at 41 Pleasant Street, Woodstock, VT 05091 is currently listed for sale with an asking price of $2,599,000. This property was built in 1899 and has 9 bedrooms and 11 full baths with 5993 sq. ft. Pleasant Street is located within the Woodstock UHSD 4 school district. Search Woodstock real estate on crystalathas.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Storage Space, Unfinished
Basement: Yes
Cooling: Wall AC Units
Heating: Propane, Oil
Home Style: Victorian
Lot Size: 0.46 Acres
Roof Type: Metal, Standing Seam
Stories: 2.5
Taxes: $33,925
Year Built: 1899

Amenities

Bar
Ceiling Fan
Dining Area
Gas Fireplace
1 Fireplace
In-Law/ADU
Primary BR w/ BA
Natural Woodwork
Security
Walk-in Closet
Wet Bar
Whirlpool Tub
1st Floor Laundry
Balcony
Garden Space
Natural Shade
Patio
Covered Porch

Feature Descriptions

Appliances: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Gas Range, Refrigerator, Washer, Gas Stove, Water Heater
Baths Full: 11
Color: Pink
Construction: Post and Beam, Wood Frame
Construction Status: Existing
Days on Site: 214
Driveway: Paved
Electric: 200+ Amp Service
Equipment: CO Detector, Security System, Smoke Detector, Sprinkler System, Gas Stove
Exterior: Post and Beam, Wood Frame
Flood Zone: No
Flooring: Carpet, Manufactured, Tile, Wood
Foundation: Brick, Concrete
Lot: Landscaped, Level, Sidewalks, In Town, Near Paths, Near Shopping, Neighborhood, Near Public Transportatn
Number of Rooms: 16
Parking: On-Site, Parking Spaces 1 - 10
Road Frontage: 114
Roads: Paved, Public
Sewer: Public
Sq. Ft. Above Grade Finished: 5993
Sq. Ft. Total Finished: 5993
Total Stories: 2.5
Water: Public
Zoning: Non-residential

Local Schools

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

Listed By / Shown By

Listed By

Agency Name: KW Vermont Woodstock
Agency Contact: Cell: 203-912-8173
Agent Name: Jennifer Falvey

agent picture

Shown By

Agent Name: Crystal Athas
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

IDX logo

TOUR THIS HOME

Choose a date and time to see 41 Pleasant Street, Woodstock, VT 05091.
I will get in touch with you shortly.

Request a Showing
Choose your video chat app
  • Friday April 24
  • Saturday April 25
  • Sunday April 26
  • Monday April 27
  • Tuesday April 28
  • Wednesday April 29
  • Thursday April 30
  • Friday May 1
  • Saturday May 2
  • Sunday May 3
  • Monday May 4
  • Tuesday May 5
  • Wednesday May 6
  • Thursday May 7
  • Friday May 8
  • 7:00 AM
  • 7:30 AM
  • 8:00 AM
  • 8:30 AM
  • 9:00 AM
  • 9:30 AM
  • 10:00 AM
  • 10:30 AM
  • 11:00 AM
  • 11:30 AM
  • 12:00 PM
  • 12:30 PM
  • 1:00 PM
  • 1:30 PM
  • 2:00 PM
  • 2:30 PM
  • 3:00 PM
  • 3:30 PM
  • 4:00 PM
  • 4:30 PM
  • 5:00 PM
  • 5:30 PM
  • 6:00 PM
  • 6:30 PM
  • 7:00 PM
  • 7:30 PM
  • 8:00 PM
  • 8:30 PM
  • 9:00 PM
Preferred Communication Method

Estimate Your Payment

Estimated Payment

$ 9,369.37 per month $5,784.25 Principal & Interest $2,827.08 Property Tax $758.04 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 04/23/2026. The listing information on this page last changed on 04/23/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 04/23/2026 5:13:11 PM EST) or MLSPIN MLS (last updated Thu 04/23/2026 5:10:50 PM EST) or Prime MLS (last updated Thu 04/23/2026 5:08:05 PM EST) or MREIS (last updated Thu 04/23/2026 5:07:13 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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 2026-04-23 17:08:05

Privacy Policy / DMCA Notice / ADA Accessibility

Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


Login to My Homefinder

Pixel