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This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining room/kitchen area. In addition, this is an income-producing property with an accessory living apartment that has a separate entrance. Offset expenses, enjoy multigenerational living, or merge and expand the home back to a single family. The interior, though updated, with a fully modern kitchen and bath, maintains the best of its original features, such as exposed beams, built-ins, large windows, and hardwood floors. The attached antique barn with a workbench is an inviting space for projects or to utilize as a studio. This property offers many choices. The stonework, gardens, and detached, expansive two-car garage all add to the desirability. New oil tank in 2024 and you will be impressed with the condition, the privacy, the large lot, and all the accessible amenities in Brattleboro, as well as the eclectic community at large. Delayed showings until Sat Sept. 13th by appointment.

More Info

Tax Information

  • Tax Year2025

Location

  • Building Number105
  • StreetChestnut Street
  • TownBrattleboro
  • StateVT
  • Zip05301
  • CountyWindham
  • Elementary SchoolBrattleboro Elem Schools
  • Junior HighBrattleboro Area Middle School
  • High SchoolBrattleboro High School
  • Flood Zone Y/NNo
  • Address105 Chestnut Street

Interior

  • Interior FeaturesDining Area, In-Law/Accessory Dwelling, Kitchen/Dining, Soaking Tub,1st Floor Laundry
  • Room 1 TypeKitchen/Dining
  • Room 1 Level1
  • Room 1 Dimensions11.8x21.2
  • FloorsCarpet, Hardwood, Tile
  • Room 2 TypeBathroom Full
  • Room 2 Level1
  • Room 2 Dimensions7.3x12.2
  • Room 3 TypeLiving/Dining
  • Room 3 Level1
  • Room 3 Dimensions12.9x21.4
  • Room 4 TypeBedroom
  • Room 4 Level1
  • Room 4 Dimensions14.5x15.2
  • Room 5 TypeBedroom
  • Room 5 Level2
  • Room 5 Dimensions9.4x14.8
  • Stories2
  • Room 6 TypeBedroom
  • Room 6 Level2
  • Room 6 Dimensions9.10x11.9

Parking

  • Parking Spaces2
  • GarageYes
  • Parking DescriptionDriveway, Garage, Off Street, Paved, Detached

Building

  • Year Built1895
  • Building ConstructionVinyl Siding
  • ConstructionExisting
  • Property StyleMulti-Family
  • Bedrooms4
  • Bathroom2
  • Total Baths2
  • Total Rooms11
  • Square Feet2,715
  • APX Unfin Below Grade660
  • BasementConcrete Floor, Dirt, Full, Interior Stairs
  • FoundationStone

Exterior

  • Exterior FeaturesBarn, Deck, Outbuilding
  • Exterior Colorwhite
  • RoofMetal, Asphalt Shingle, Slate

Amenities

  • Accessibility Amenities1st Floor Bedroom,1st Floor Full Bathroom,1st Floor Hrd Surfce Flr,1st Floor Laundry
  • PricePerSqFt145.49

Other

  • Delayed ShowingsYes
  • Date Showings Begin2025-09-13
  • SeasonalNo
  • Page799-800
  • Date Listed09/09/2025
  • View Count1

Rooms

  • Full Bath2

Basic Information

  • MLS Number5060368
  • MLS StatusActive Under Contract
  • Virtual TourView Tour
  • StatusActive With Contract
  • Property TypeSingle Family
  • List Price$395,000
  • Listing Agent NameKristen Ziter Taylor
  • Broker NameBrattleboro Area Realty

Property

  • Acreage0.78
  • Lot DescriptionSidewalks, Street Lights
  • AreaVT-Windham
  • DrivewayCircular, Paved
  • RoadsCul-de-Sac, Paved, Public
  • Road Frontage135

Utilities

  • Heat SystemOil, Baseboard
  • WaterPublic
  • SewerPublic
  • Electric100 Amp Service
  • UtilitiesCable Available, Telephone Available

Map Location

Driving Directions

Broker Reciprocity 

Copyright 2025 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 November 12, 2025 9:08 AM EST

 

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