Skip main navigation
Active
  • Listed by: Barrett and Valley Associates Inc.
    Price cut: $50K (1/30)
    $399,000

    1397 Popple Dungeon Road, Chester, VT 05143

    3beds
    1,788sqft
    : 
    Single Family Residence
    Built in 1900
    3.3 Acres Lot
    $-- Zestimate®
    $223/sqft
    $-- HOA

    What's special

    Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below—perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there’s room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery—rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont’s natural beauty. A property that offers privacy, water frontage, land, and mountain access—without giving up convenience.
    71 days
    |
    2,295
    |
    108
    |

    Zillow last checked: 7 hours ago

    Listing updated: January 30, 2026 at 06:08am

    Listed by:

    Daire Gibney,

    Barrett and Valley Associates Inc. 802-875-2323

    Source: PrimeMLS,MLS#: 5073930MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 1
      • 3/4 bathrooms: 1
      Heating
      • Oil
      Cooling
      • None
      Features
      • Basement: Concrete,Concrete Floor,Unfinished,Interior Access,Interior Entry
      Interior area
      • Total structure area: 2,240
      • Total interior livable area: 1,788 sqft
      • Finished area above ground: 1,788
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 1
      • Parking features: Paved
      • Garage spaces: 1
      Features
      • Levels: Two
      • Stories: 2
      • Waterfront features: River Front
      • Frontage length: Road frontage: 800
      Lot
      • Size: 3.3 Acres
      • Features: Country Setting
      Details
      • Parcel number: 14404511573
      • Zoning description: Resiential

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape
      • Property subtype: Single Family Residence
      Materials
      • Wood Frame
      • Foundation: Concrete
      • Roof: Asphalt Shingle
      Condition
      • New construction: No
      • Year built: 1900

      Utilities & green energy

      • Electric: Circuit Breakers
      • Sewer: Private Available
      • Utilities for property: Phone Available

      Community & HOA

      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $223/sqft
      • Tax assessed value: $232,900
      • Annual tax amount: $6,786
      • Date on market: 1/14/2026
      • Road surface type: Paved
      Get pre-qualifiedBe ready to make an offer.
      Connect with an agentGet info on this home, tour, and more.
      Calculate monthly paymentSee if you can afford this home.

        Estimated market value

        Not available

        Estimated sales range

        Not available

        $2,787/mo

        Price history

        Price history
        DateEventPrice
        1/30/2026Price change$399,000-11.1%$223/sqft
        Source: PrimeMLS #5073930 Report a problem
        1/14/2026Listed for sale$449,000+277.3%$251/sqft
        Source: PrimeMLS #5073930 Report a problem
        8/24/2001Sold$119,000$67/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024-- $232,900
        2023-- $232,900
        2022-- $232,900
        2021-- $232,900
        2020-- $232,900 -2.1%
        2019-- $237,900
        2018-- $237,900
        2017-- $237,900
        2016-- $237,900 +9900%
        2015-- $2,379
        2014-- $2,379
        2013-- $2,379
        2012-- $2,379
        2011-- $2,379
        2010-- $2,379
        2009-- $2,379
        2008-- $2,379 +98.4%
        2007-- $1,199
        2006-- $1,199
        2003$3,057 $1,199

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $2,716/mo
        Principal & interest
        $2058
        Property taxes
        $658
        More affordability tools

          Climate risks

          Neighborhood: 05143

          Getting around

          0 / 100
          Car-Dependent

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Chester-Andover Elementary
          • Middle: Green Mountain UHSD #35
          • High: Green Mountain UHSD #35
          • District: Two Rivers Supervisory Union

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

          Local experts in 05143

          Similar homes

          Skip to the end of the carouselSkip to the beginning of the carousel