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  • Listed by: 

    Kristen Ziter Taylor,

    Brattleboro Area Realty 802-257-1335

    Bought with: Brattleboro Area Realty
    $395,000

    105 Chestnut Street, Brattleboro, VT 05301

    4beds
    2,715sqft
    Multi Family
    Built in 1895
    -- sqft lot
    $394,300 Zestimate®
    $145/sqft
    $1,687 Estimated rent

    Home value

    $394,300

    $268,000 - $584,000

    $1,687/mo

    Zestimate® history
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    What's special

    A very special two unit! The main house is a spacious 3 bedroom, 1 bath with a primary bedroom and laundry on the first floor. The second unit is a desirable 1 bedroom, 1 bath. 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. 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. Perhaps add a third unit? This property offers many choices. The stonework, gardens, and detached, expansive two-car garage all add to the desirability. You will be impressed with the new oil tank in 2024, 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.

    Zillow last checked: 7 hours ago

    Listing updated: November 21, 2025 at 10:53am

    Listed by:

    Kristen Ziter Taylor,

    Brattleboro Area Realty 802-257-1335

    Bought with:

    Kristen Ziter Taylor

    Brattleboro Area Realty

    Source: PrimeMLS,MLS#: 5060371MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Oil, Baseboard
    Cooling
    • None
    Features
    • Flooring: Carpet, Hardwood, Tile
    • Basement: Concrete Floor,Dirt,Full,Interior Stairs,Interior Entry
    Interior area
    • Total structure area: 3,375
    • Total interior livable area: 2,715 sqft
    • Finished area above ground: 2,715
    • Finished area below ground: 0

    Property

    Parking
    • Total spaces: 2
    • Parking features: Circular Driveway, Paved, Detached, Driveway, Garage, Off Street
    • Garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Levels: Two
    • Exterior features: Deck
    • Frontage length: Road frontage: 135
    Lot
    • Size: 0.78 Acres
    • Features: Level, Sidewalks, Street Lights
    Details
    • Additional structures: Barn(s), Outbuilding
    • Parcel number: 8102514542
    • Zoning description: Res

    Construction

    Type & style
    • Home type: MultiFamily
    • Property subtype: Multi Family
    Materials
    • Vinyl Siding
    • Foundation: Brick, Stone
    • Roof: Metal,Asphalt Shingle,Slate
    Condition
    • New construction: No
    • Year built: 1895

    Utilities & green energy

    • Electric: 100 Amp Service
    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: Cable Available, Phone Available

    Community & neighborhood

    Location
    • Region: Brattleboro

    Price history

    DateEventPrice
    11/20/2025Sold$395,000$145/sqft
    Source: PrimeMLS #5060371 Report a problem
    9/9/2025Listed for sale$395,000$145/sqft
    Source: PrimeMLS #5060368 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024-- $226,870
    2023-- $226,870
    2022-- $226,870

    Find assessor info on the county website

    Neighborhood: 05301

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Brattleboro Elem Schools
    • Middle: Brattleboro Area Middle School
    • High: Brattleboro High School

    Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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