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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
    $505,600 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!!
    118 days
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    5,244
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    397
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    Zillow last checked: 8 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
    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

    $505,600

    $480,000 - $531,000

    $5,551/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
    $3,383/mo
    Principal & interest
    $2510
    Property taxes
    $873

      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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