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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.

More Info

Tax Information

  • Tax Year2025

Location

  • Building Number211
  • StreetPleasant Valley Road
  • TownBrattleboro
  • StateVT
  • Zip05301
  • CountyWindham
  • Flood Zone Y/NNo
  • Address211 Pleasant Valley Road

Property

  • Acreage5.9
  • Lot DescriptionAgricultural, Country Setting, Field/Pasture, Level, Sloping, Trail/Near Trail, View, Wooded, Near Country Club, Near Golf Course, Near Skiing, Rural, Near Hospital, Private
  • AreaVT-Windham
  • DrivewayGravel
  • RoadsGravel, Public Maintained Road
  • Road Frontage650

Utilities

  • Heat SystemOil, Hot Air
  • WaterDrilled Well
  • SewerOn-Site Septic Exists
  • Electric100 Amp Service
  • UtilitiesPhone, Cable

Other

  • SeasonalNo
  • Page986
  • Date Listed06/14/2026

Parking

  • Parking Spaces2
  • GarageYes

Building

  • Year Built1942
  • Building ConstructionWood Frame, Vertical Siding, Wood Siding
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms2
  • Bathroom1
  • Total Baths1
  • Total Rooms5
  • Square Feet1,576
  • APX Unfin Below Grade200
  • BasementPartial, Partially Finished, Interior Stairs, Storage Space, Walkout
  • FoundationBlock, Concrete, Poured Concrete

Exterior

  • Exterior FeaturesBarn, Deck, Garden Space, Natural Shade, Storage
  • Exterior ColorBrown
  • RoofFlat, Membrane

Amenities

  • PricePerSqFt493.66

Rooms

  • Full Bath1

Basic Information

  • MLS Number5094642
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$545,000
  • Listing Agent NameChris Long
  • Broker NameBHG Masiello Brattleboro

Interior

  • Interior Features1 Fireplace, Hearth, Living/Dining, Natural Light, Natural Woodwork, Skylight, Wood Stove Hook-up, Basement Laundry
  • Room 1 TypeKitchen
  • Room 1 Level1
  • Room 1 Dimensions10' X 17'
  • FloorsCarpet, Laminate, Vinyl
  • Room 2 TypeLiving/Dining
  • Room 2 Level1
  • Room 2 Dimensions13'6" X 22'6"
  • Room 3 TypeBedroom
  • Room 3 Level1
  • Room 3 Dimensions9' X 19'
  • Room 4 TypeBedroom
  • Room 4 Level1
  • Room 4 Dimensions10' X 12'
  • Room 5 TypeFamily Room
  • Room 5 LevelBasement
  • Room 5 Dimensions12' X 33'
  • Stories1

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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 June 15, 2026 8:23 AM UTC

 

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