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

2 High Street, Woodstock, VT 05091

$1,199,000
  • Main Photo

60 Total Photos [Click to View All]

New to the Market Active
BEDS3 BATHS3 full SQUARE FEET1,950 MLS#5094456
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWindsor Central

Listing Courtesy of: Bassette Real Estate Group
Agency Phone: 802-457-2244
Associate Name: John Bassette
IDX logo


Property Description

Beautifully Restored all the way down to the studs, c. 1890 Village Home in the Heart of downtown Woodstock! Extensively renovated while preserving its historic charm, this 3-bedroom, 3-bathroom residence offers the perfect blend of character and modern convenience right in the center of EVERYTHING. Major renovations and improvements include updated spray foam insulation, walls, windows, wiring, flooring, appliances, even structural supports, and dual new heating systems with Central AC. Abundant natural light highlight the home's timeless appeal and the new deck over the garage insures you won't miss any of the action in town. The main level features a sun-filled living room with fireplace, private study with adjoining 3/4 bath, and an open-concept kitchen and dining area with quartz countertops, stainless appliances, and direct access to a welcoming covered porch overlooking the quaint New England charm of downtown Woodstock. Upstairs are three bedrooms, including a spacious primary suite with private bath and double closets. A second full bath features a tiled shower, soaking tub, and new Washer & Dryer. The finished third floor provides an exceptional bonus space ideal for a family room, office, studio, playroom, or guest accommodations, along with a separate storage room. Additional amenities include a paved driveway, lower-level garage/storage area, town water and sewer, dual Bosch propane boilers, propane 75G hot water, central air conditioning, and low-maintenance village living. Enjoy being just steps from Woodstock's renowned restaurants, shops, galleries, recreation, and community events. A rare opportunity to own a move-in-ready historic home in one of Vermont's most desirable village locations.

2 High Street | MLS# 5094456

This single family home located at 2 High Street, Woodstock, VT 05091 is currently listed for sale with an asking price of $1,199,000. This property was built in 1890 and has 3 bedrooms and 3 full baths with 1950 sq. ft. High Street is located within the Windsor Central school district. Search Woodstock real estate on aydenhardy.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Insulated, Interior Stairs, Storage Space, Unfinished, Interior Access
Cooling: Central AC
Garage: 1 car attached
Heating: Propane, Forced Air, In Ceiling, In Floor, Multi Zone
Home Style: Colonial, Farmhouse
Lot Size: 0.07 Acres
Roof Type: Slate
Stories: 2.5
Taxes: $9,907
Year Built: 1890

Amenities

Blinds
Ceiling Fan
Dining Area
Gas Fireplace
1 Fireplace
Kitchen Island
2nd Floor Laundry
Walkup Attic
Deck
Covered Porch
Low E Window(s)

Feature Descriptions

Appliances: Dishwasher, Dryer, Range Hood, Microwave, Electric Range, Refrigerator, Washer, Propane Water Heater, Owned Water Heater, Wine Cooler
Baths 3/4: 2
Baths Full: 1
Color: White
Construction: Wood Frame, Clapboard Exterior, Vinyl Siding, Wood Exterior
Construction Status: Existing
Driveway: Paved
Electric: 200+ Amp Service, Circuit Breaker(s)
Equipment: CO Detector, Smoke Detector
Exterior: Wood Frame, Clapboard Exterior, Vinyl Siding, Wood Ex
Flood Zone: No
Flooring: Carpet, Tile, Wood
Foundation: Fieldstone, Stone
Lot: City Lot, Hilly, Mountain View, In Town, Near Country Club, Near Golf Course, Near Paths, Near Shopping, Neighborhood, Near School(s)
Number of Rooms: 7
Parking: Attached
Road Frontage: 60
Roads: Paved, Public
Sewer: Public
Sq. Ft. Above Grade Finished: 1950
Sq. Ft. Total Finished: 1950
Total Stories: 2.5
Water: Public
Zoning: Residential High Density

Room Sizes

Living Room: 12.2 x 14.4 Level - 1
Dining Room: 14.2 x 13.5 Level - 1
Kitchen: 14 x 10 Level - 1
Office/Study: 8.7 x 8.6 Level - 1
Bedroom: 10.1 x 10 Level - 2
Primary BR Suite: 12.5 x 12.2 Level - 2
Bedroom: 10.2 x 10 Level - 2
Bathroom Full: 8.4 x 11.6 Level - 2
Family Room: 11.6 x 28 Level - 3

Local Schools

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

Listed By / Shown By

Listed By

Agency Name: Bassette Real Estate Group
Agent Name: John Bassette
Agency Phone: 802-457-2244

Shown By

Agent Name: Ayden Hardy
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 2 High Street, Woodstock, VT 05091.
I will get in touch with you shortly.

Request a Showing
Choose your video chat app
  • Saturday June 13
  • Sunday June 14
  • Monday June 15
  • Tuesday June 16
  • Wednesday June 17
  • Thursday June 18
  • Friday June 19
  • Saturday June 20
  • Sunday June 21
  • Monday June 22
  • Tuesday June 23
  • Wednesday June 24
  • Thursday June 25
  • Friday June 26
  • Saturday June 27
  • 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

$ 3,843.75 per month $2,668.45 Principal & Interest $825.58 Property Tax $349.71 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 06/12/2026. The listing information on this page last changed on 06/12/2026. 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 Fri 06/12/2026 12:01:37 AM EST) or MLSPIN MLS (last updated Thu 06/11/2026 11:38:53 PM EST) or Prime MLS (last updated Thu 06/11/2026 11:33:22 PM EST) or MREIS (last updated Thu 06/11/2026 11:55:26 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 2026-06-11 23:33:22

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