Woodstock, VT | 45 Pleasant Street

Christie's International Real Estate
$1,595,000
MLS#: 5115063
3,154
Sq Ft
0.31
Acres
6
Baths
5
Bedrooms
General Property Information
Property Status
Active
Price
$1, 595, 000
Property Type
Single Family
County
VT-Windsor
Agency / Brokerage
Gail Childs
Covered Bridge RE
List Date
10/20/2026 8:00 PM
Acres
0.31
Year Built
1900
Bedrooms
5
Total Baths
6
Sq. Ft. (Total)
3,154
Tax Year
2026
Taxes
$20,456

Description

Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

Map

Interior Features
# Of Stories
3
Sq. Ft. (Total)
3,154
Sq. Ft. (Above Ground)
3,154
Sq. Ft. (Below Ground)
0
Rooms
10
Bedrooms
5
Baths
6
Heating
Propane, Multi Zone, Radiator, Boiler
Basement Desc
Bulkhead, Walkout, Interior Access, Exterior Access

Town Market Snapshot

Source: Data provided by PrimeMLS, graph generated by Pall Spera Company

Exterior Features
Style of Residence
Antique, Colonial, Historic Vintage, Multi-Family
Time Share
No
Land Desc.
Landscaped, In Town
Roof Desc.
Standing Seam
Driveway Desc.
Gravel
Foundation Desc.
Brick, Stone
Sewer Desc.
Public
Garage / Parking
No
Garage Spaces
0
Road Frontage
0
Zoning
RHD
Elementary School
Woodstock Elementary School
Middle School
Woodstock Union Middle Sch
High School
Woodstock Senior UHSD #4

Affordability Estimate

Quick payment estimate for this listing. Not a loan offer — rates and terms vary.

Est. monthly principal & interest —

  • Loan amount: —
  • Down payment: —

Estimate excludes taxes, insurance, HOA, and PMI. Consult a lender for accurate figures.

You May Also Like

View more nearby