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  • Listed by: BHG Masiello Brattleboro • Chris Long
    Bought with: Flex Realty
    $525,000

    211 Pleasant Valley Road, Brattleboro, VT 05301

    2beds
    1,576sqft
    Single Family Residence
    Built in 1942
    5.9 Acres Lot
    $527,700 Zestimate®
    $333/sqft
    $1,900 Estimated rent

    Home value

    $527,700

    $501,000 - $554,000

    $1,900/mo

    Zestimate® history
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    What's special

    Distinctive contemporary homeStriking flat roof designClassic gambrel two-story barnClean mid-century modern influencesRedwood siding
    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.

    Zillow last checked:

    Listing updated:

    Listed by:

    Chris Long,

    BHG Masiello Brattleboro 802-257-1111

    Bought with:

    Grayson VanHendrick

    Flex Realty

    Source: PrimeMLS,MLS#: 5094642MLS Logo

    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: $333/sqft
    • Tax assessed value: $270,820
    • Annual tax amount: $9,431
    • Date on market: 6/14/2026
    • Road surface type: Gravel

    Price history

    DateEventPrice
    8/31/2026Sold$525,000-3.7%$333/sqft
    Source: PrimeMLS #5094642 Report a problem
    6/14/2026Listed for sale$545,000$346/sqft
    Source: PrimeMLS #5094642 Report a problem

    Public tax history

    YearProperty taxesTax 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

    Neighborhood: 05301

    Nearby schools

    GreatSchools rating
    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $527,700
    2% more
    +$10,554
    With Zillow Showcase(estimated)
    $538,254
    Sell for more on Zillow
    Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
    $527,700
    2% more
    +$10,554
    With Zillow Showcase(estimated)
    $538,254