Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.
Active
Listed by: BHG Masiello Brattleboro
$545,000
211 Pleasant Valley Road, Brattleboro, VT 05301
2beds
1,576sqft
Single Family Residence
Built in 1942
5.9 Acres Lot
$529,900 Zestimate®
$346/sqft
$-- HOA
What's special
Distinctive contemporary homeStriking flat roof designClassic gambrel two-story barnClean mid-century modern influencesRedwood siding
- 4 days |
- 1,034 |
- 70 |
Zillow last checked:
Listing updated:
Listed by:
Chris Long,
BHG Masiello Brattleboro 802-257-1111
Source: PrimeMLS,MLS#: 5094642
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Heating
- Oil, Hot Air
Cooling
- Central Air
Appliances
- Included: Microwave, Electric Range, Refrigerator
- Laundry: In Basement
Features
- Hearth, Living/Dining, Natural Light, Natural Woodwork
- Flooring: Carpet, Laminate, Vinyl
- Windows: Skylight(s)
- Basement: Partial,Partially Finished,Interior Stairs,Storage Space,Walkout,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: 1 Fireplace, Wood Stove Hook-up
Interior area
- Total structure area: 1,776
- Total interior livable area: 1,576 sqft
- Finished area above ground: 1,104
- Finished area below ground: 472
Property
Parking
- Total spaces: 2
- Parking features: Gravel
- Garage spaces: 2
Features
- Levels: One
- Stories: 1
- Exterior features: Deck, Garden, Natural Shade, Storage
- Has view: Yes
- Frontage length: Road frontage: 650
Lot
- Size: 5.9 Acres
- Features: Agricultural, Country Setting, Field/Pasture, Level, Sloped, Trail/Near Trail, Views, Wooded, Near Country Club, Near Golf Course, Near Skiing, Rural, Near Hospital
Details
- Additional structures: Barn(s)
- Parcel number: 8102513594
- Zoning description: res
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Vertical Siding, Wood Siding
- Foundation: Block, Concrete, Poured Concrete
- Roof: Flat,Membrane
Condition
- New construction: No
- Year built: 1942
Utilities & green energy
- Electric: 100 Amp Service
- Sewer: On-Site Septic Exists
- Utilities for property: Phone, Cable
Community & HOA
Location
- Region: Brattleboro
Financial & listing details
- Price per square foot: $346/sqft
- Tax assessed value: $270,820
- Annual tax amount: $9,431
- Date on market: 6/14/2026
- Road surface type: Gravel
Estimated market value
$529,900
$503,000 - $556,000
$3,058/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/14/2026 | Listed for sale | $545,000$346/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $270,820 |
| 2023 | -- | $270,820 |
| 2022 | -- | $270,820 |
| 2021 | -- | $270,820 |
| 2020 | -- | $270,820 |
| 2019 | -- | $270,820 |
| 2018 | -- | $270,820 |
| 2017 | -- | $270,820 |
| 2016 | -- | $270,820 +9900.7% |
| 2015 | -- | $2,708 |
| 2014 | -- | $2,708 |
| 2013 | -- | $2,708 |
| 2012 | -- | $2,708 |
| 2011 | -- | $2,708 |
| 2010 | -- | $2,708 +20.4% |
| 2009 | -- | $2,249 |
| 2008 | -- | $2,249 |
| 2007 | -- | $2,249 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
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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Climate risks
Neighborhood: 05301
Nearby schools
GreatSchools rating
- 6/10Academy SchoolGrades: PK-6Distance: 1.9 mi
- 6/10Brattleboro Area Middle SchoolGrades: 7-8Distance: 3.6 mi
- NAWindham Regional Career CenterGrades: 9-12Distance: 3.6 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Vermont
- Windham County
- Brattleboro
- 05301
- 211 Pleasant Valley Road



