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  • Listed by: Barrett and Valley Associates Inc.
    $529,000

    514 First Avenue, Chester, VT 05143

    5beds
    3,880sqft
    : 
    Single Family Residence
    Built in 1803
    4.8 Acres Lot
    $507,900 Zestimate®
    $136/sqft
    $-- HOA

    What's special

    Two fireplacesHistoric districtsDurable early craftsmanshipOriginal wood floorsExposed beamsRoom for gardenFormal dining room
    Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous room off the kitchen easily accommodates larger meals and celebrations. Original wood floors, exposed beams, and durable early craftsmanship add character throughout. A separate rental unit, currently occupied, provides steady income or flexible use for guests, family, or workspace. The barn offers storage, workshop potential, or agricultural use, expanding what the property can support. Chester’s shops and everyday conveniences are close by, and skiing, rivers, and trails are within easy reach. Okemo is just minutes away, with Stratton, Magic, and Bromley all within a short drive of 20-30 minutes. Several AT access point within similar distance. The Okemo Valley is on your doorstep, and it's magical! This is a historic home ready for its next chapter—solid, adaptable, and full of possibility. Come See Today!!
    135 days
    |
    4,603
    |
    347
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    Zillow last checked: 7 hours ago

    Listing updated: November 10, 2025 at 08:22am

    Listed by:

    Daire Gibney,

    Barrett and Valley Associates Inc. 802-875-2323

    Source: PrimeMLS,MLS#: 5068855MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 4
      • 3/4 bathrooms: 1
      Heating
      • Oil, Zoned, Radiator
      Cooling
      • None
      Features
      • Basement: Concrete,Interior Access,Interior Entry
      Interior area
      • Total structure area: 4,380
      • Total interior livable area: 3,880 sqft
      • Finished area above ground: 3,880
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Gravel, Paved
      • Garage spaces: 2
      Features
      • Levels: 3
      • Stories: 3
      • Frontage length: Road frontage: 1599
      Lot
      • Size: 4.8 Acres
      • Features: Corner Lot, Country Setting, Horse/Animal Farm, Field/Pasture, Major Road Frontage
      Details
      • Parcel number: 14404511490
      • Zoning description: Residential

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Masonry, Brick Exterior
      • Foundation: Brick, Concrete, Stone
      • Roof: Metal,Shingle,Slate
      Condition
      • New construction: No
      • Year built: 1803

      Utilities & green energy

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

      Community & HOA

      Location
      • Region: Chester

      Financial & listing details

      • Price per square foot: $136/sqft
      • Tax assessed value: $329,400
      • Annual tax amount: $9,598
      • Date on market: 11/7/2025
      • Road surface type: Paved
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        Estimated market value

        $507,900

        $483,000 - $533,000

        $4,878/mo

        Price history

        Price history
        DateEventPrice
        11/7/2025Listed for sale$529,000-2.8%$136/sqft
        Source: PrimeMLS #5068855 Report a problem
        11/18/2023Listing removed--
        Source: PrimeMLS #4954146 Report a problem
        7/12/2023Price change$544,500-0.9%$140/sqft
        Source: PrimeMLS #4954146 Report a problem
        6/28/2023Listed for sale$549,500$142/sqft
        Source: PrimeMLS #4954146 Report a problem
        6/28/2023Contingent$549,500$142/sqft
        Source: PrimeMLS #4954146 Report a problem
        6/22/2023Listed for sale$549,500$142/sqft
        Source: PrimeMLS #4954146 Report a problem
        6/6/2023Contingent$549,500$142/sqft
        Source: PrimeMLS #4954146 Report a problem
        5/24/2023Listed for sale$549,500+44.6%$142/sqft
        Source: PrimeMLS #4954146 Report a problem
        8/20/2021Sold$380,000+0.3%$98/sqft
        Source: PrimeMLS #4861178 Report a problem
        5/22/2021Contingent$379,000$98/sqft
        Source: PrimeMLS #4861178 Report a problem
        5/17/2021Listed for sale$379,000+13.1%$98/sqft
        Source: PrimeMLS #4861178 Report a problem
        2/23/2018Listing removed$335,000$86/sqft
        Source: Coldwell Banker Watson Realty #4493693 Report a problem
        9/16/2016Price change$335,000-4%$86/sqft
        Source: Coldwell Banker Watson Realty/ Ludlow #4493693 Report a problem
        5/27/2016Listed for sale$349,000-6.8%$90/sqft
        Source: Coldwell Banker Watson Realty/ Ludlow #4493693 Report a problem
        1/11/2015Listing removed$374,500$97/sqft
        Source: Barrett & Valley Associates Inc #4372684 Report a problem
        7/22/2014Price change$374,500-0.1%$97/sqft
        Source: Barrett & Valley Associates Inc #4372684 Report a problem
        4/10/2014Price change$375,000-6%$97/sqft
        Source: Nextage Welcom realty #4233722 Report a problem
        7/12/2013Price change$399,000-6.1%$103/sqft
        Source: Nextage Welcom realty #4233722 Report a problem
        5/2/2013Listed for sale$425,000+9%$110/sqft
        Source: Nextage Welcom realty #4233722 Report a problem
        4/20/2012Sold$390,000-18.7%$101/sqft
        Source: Public Record Report a problem
        4/25/2008Sold$479,788+110.9%$124/sqft
        Source: Public Record Report a problem
        10/28/1998Sold$227,500$59/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024-- $329,400
        2023-- $329,400
        2022-- $329,400 -0.2%
        2021-- $330,100
        2020-- $330,100 +0.7%
        2019-- $327,700
        2018-- $327,700
        2017-- $327,700
        2016-- $327,700 +6729.9%
        2015-- $4,798
        2014-- $4,798
        2013-- $4,798
        2012-- $4,798 -13.5%
        2011-- $5,550
        2010-- $5,550
        2009-- $5,550
        2008-- $5,550 +92.4%
        2007-- $2,884
        2006-- $2,884
        2003$7,354 $2,884

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $3,601/mo
        Principal & interest
        $2728
        Property taxes
        $873
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          Climate risks

          Neighborhood: Chester-Chester Depot

          Getting around

          22 / 100
          Car-Dependent
          28 / 100
          Somewhat Bikeable

          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.

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