2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern convenience with original charm. The first floor features oversized, recently updated windows and several spacious high ceiling gathering rooms including a formal living room, dining room, library, and central family room. A cozy eat-in kitchen with fireplace on the north side of the house opens to a lovely landscaped yard shaded by mature maple trees. The second floor, also punctuated by high ceilings and windows to give it a bright and spacious feel, features a primary bedroom on the front side of the house with an adjoining dressing area, walk in closets, and full bath. Adjacent the primary is another sizable bedroom with its own bath, while two additional bedrooms with shared bath round out the level. The detached barn garage has space for one car and plenty of additional storage. Idyllically sited and within walking distance of local shopping, dining, schools, hiking trails, and Marsh-Billings-Rockefeller National Historic Park, this iconic Woodstock home is a rare gem.
Closed
Listed by:
David Donegan,
Snyder Donegan Real Estate Group Cell:603-443-0044
Bought with: Williamson Group Sothebys Intl. Realty
$2,350,000
2 Pleasant Street, Woodstock, VT 05091
4beds
3,998sqft
Single Family Residence
Built in 1821
0.37 Acres Lot
$2,469,600 Zestimate®
$588/sqft
$5,118 Estimated rent
Home value
$2,469,600
$2.35M - $2.59M
$5,118/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: December 08, 2025 at 06:50am
Listed by:
David Donegan,
Snyder Donegan Real Estate Group Cell:603-443-0044
Bought with:
Gretchjen Smith
Williamson Group Sothebys Intl. Realty
Source: PrimeMLS,MLS#: 5057220
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Propane, Baseboard
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Microwave, Electric Range, Washer
- Laundry: 1st Floor Laundry
Features
- Bar, Dining Area, Kitchen/Family, Natural Light, Natural Woodwork, Walk-In Closet(s)
- Flooring: Brick, Hardwood, Slate/Stone, Softwood
- Windows: Screens
- Basement: Concrete Floor,Unfinished,Interior Entry
- Attic: Attic with Hatch/Skuttle
- Has fireplace: Yes
- Fireplace features: Wood Burning, 3+ Fireplaces, Wood Stove Hook-up
Interior area
- Total structure area: 5,310
- Total interior livable area: 3,998 sqft
- Finished area above ground: 3,998
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Paved, Driveway, Garage
- Garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, 1st Floor Laundry
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered Porch
- Exterior features: Garden, Natural Shade, Storage
- Fencing: Partial
- Frontage length: Road frontage: 600
Lot
- Size: 0.37 Acres
- Features: Corner Lot, Landscaped, Level, Sidewalks, Trail/Near Trail, Near Country Club, Near Golf Course, Near Shopping, Near Skiing, Neighborhood, Near School(s)
Details
- Parcel number: 78625010406
- Zoning description: Res
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Federal
- Property subtype: Single Family Residence
Materials
- Brick Exterior
- Foundation: Stone
- Roof: Asphalt Shingle
Condition
- New construction: No
- Year built: 1821
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Public Sewer
- Utilities for property: Cable
Community & neighborhood
Security
- Security features: Carbon Monoxide Detector(s), Smoke Detector(s)
Location
- Region: Woodstock
Other
Other facts
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 12/8/2025 | Sold | $2,350,000-9.6%$588/sqft |
Source:  PrimeMLS #5057220 | ||
| 8/19/2025 | Listed for sale | $2,600,000+108%$650/sqft |
Source: PrimeMLS #5057220 | ||
| 2/24/2021 | Sold | $1,250,000+19%$313/sqft |
Source: PrimeMLS #4848451 | ||
| 4/3/2020 | Sold | $1,050,000$263/sqft |
Source: PrimeMLS #4800400 | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $1,064,300 |
| 2023 | -- | $1,064,300 |
| 2022 | -- | $1,064,300 |
Find assessor info on the county website
Neighborhood: 05091
Nearby schools
GreatSchools rating
- 9/10Woodstock Elementary SchoolGrades: PK-4Distance: 0.4 mi
- NAWoodstock Union Middle SchoolGrades: 7-8Distance: 1.7 mi
- 9/10Woodstock Senior Uhsd #4Grades: 7-12Distance: 1.7 mi
Schools provided by the listing agent
- Elementary: Woodstock Elementary School
- Middle: Woodstock Union Middle Sch
- High: Woodstock Senior UHSD #4
- District: Woodstock UHSD 4
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.