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  • $595,000

    357 Chestnut Hill Road, Woodstock, NY 12498

    2beds
    1,338sqft
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    Single Family Residence
    Built in 1970
    1.7 Acres Lot
    $586,600 Zestimate®
    $445/sqft
    $-- HOA

    What's special

    Natural lightPrimary bedroomWarm woodsOverhead skylightSunlight spills through skylightsWood cabinetryExposed beams
    A STORYBOOK WOODSTOCK RETREAT IN THE WOODS Some homes provide shelter; others provide sanctuary. 357 Chestnut Hill Road is a sanctuary in the woods--a soulful Woodstock retreat where sunlight spills through skylights, pine glows underfoot, and the forest seems to lean in and whisper, ''stay awhile.'' Set on 1.6 wooded acres with approximately 257 feet of road frontage, this enchanting red-clad hideaway has been treasured by one close family since 1970. Follow the gravel drive beneath a leafy canopy and the home gradually reveals itself among the trees, its warm wood exterior appearing almost organically from the landscape. Secluded without feeling isolated, it captures the creative, carefree spirit that has long made Woodstock irresistible. Inside, 1,338 square feet includes a primary bedroom, a bath, a kitchen, a wonderfully versatile loft, and the home's showpiece: a spacious, cozy living room where an exposed beamed-wood ceiling creates an architectural rhythm overhead, while skylights pour pools of daylight across pine floors below. Windows frame the surrounding woodland. A characterful brick fireplace anchors it all. On crisp Catskills evenings, the hearth becomes the heart of the house--a natural gathering place for conversation, contemplation, and fireside nights. Rustic textures, warm woods, and natural light lend the room an atmosphere at once dramatic and deeply comfortable. The adjoining kitchen and dining area anchor the country cabin's soul with wood cabinetry, exposed beams, a vaulted ceiling, and an overhead skylight. Equipped with a refrigerator, range/oven, dishwasher, and washer/dryer, it is an inviting, unpretentious space for everything from pancakes at sunrise to pasta and pinot after a day exploring. And then there is the porch! Wrapping around two sides of the kitchen, the sprawling screened porch creates an irresistible indoor-outdoor area suspended within the trees. Here, the forest becomes the wallpaper and birdsong the soundtrack. Rain can patter overhead, leaves can rustle beyond the screens, and summer evenings can linger long after the sun disappears. The upper loft adds an unexpected dimension to the home's mostly single-level layout. Wrapped in warm wood, this flexible aerie can readily accommodate an additional sleeping space and a home office, library, studio, meditation area, or creative escape. Space creates possibility, and possibility gives a home room to evolve. Four split-system units add modern comfort, while a 260-square-foot partial basement provides additional utility. The house's roof was replaced in 2020. Outside, the property becomes a private woodland world. Mature trees tower overhead, sunlight dapples the forest floor, and the home's distinctive red exterior provides a warm counterpoint to the seemingly endless green. The gently winding gravel drive continues uphill to a particularly valuable feature: an oversized detached garage. With its dedicated entrance, windows, and loft storage above, the garage offers far more than parking. Think workshop, equipment storage, hobby headquarters, or simply the rare luxury of having room for all the things that make country life more enjoyable. Its roof was replaced in 2023. Yet the real luxury here cannot be quantified by acreage or square footage. It is privacy, peace, and place. For more than half a century, one family has returned to this home, lovingly cared for it, gathered within it, and called it their retreat. That continuity gives 357 Chestnut Hill Road something no renovation can manufacture: soul. The house does not ask to be something it isn't; its weathered woods, exposed beams, skylights, fireplace, loft, porch, and forest setting tell an authentic story of Woodstock country living--and invite a new owner to write its next chapter. Retreat becomes refuge; refuge becomes home; and every great story needs a place to begin--make 357 Chestnut Hill Road the beginning of yours.
    18 days
    3,141
    304

    Zillow last checked:

    Listing updated:

    Listed by:

    Brown Harris Stevens Hudson 518-828-0181,

    Jacob Miles 212-807-1552

    Source: HVCRMLS,MLS#: 20265197MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 1
      • Full bathrooms: 1
      Primary bedroom
      • Level: Main
      Bedroom
      • Description: loft-style sleeping area and den
      • Level: Second
      Bathroom
      • Level: Main
      Basement
      • Level: Basement
      Kitchen
      • Level: Main
      Living room
      • Level: Main
      Other
      • Description: Wrap-around, screened porch
      • Level: Main
      Heating
      • Fireplace(s), Forced Air
      Cooling
      • Electric
      Appliances
      • Included: Water Heater, Washer/Dryer, Washer, Refrigerator, Range Hood, Range, Oven, Freezer, Free-Standing Refrigerator, Free-Standing Freezer, Exhaust Fan, Electric Water Heater, Electric Range, Dryer, Dishwasher, Built-In Range, Built-In Electric Range, Built-In Electric Oven
      • Laundry: In Kitchen, Main Level
      Features
      • Beamed Ceilings, High Ceilings, Natural Woodwork, Other, See Remarks
      • Flooring: Hardwood, Plank, Wood
      • Windows: Screens
      • Basement: Exterior Entry,Partial,Partially Finished,Storage Space,Unfinished
      Interior area
      • Total structure area: 1,338
      • Total interior livable area: 1,338 sqft
      • Finished area above ground: 1,338
      • Finished area below ground: 260

      Property

      Parking
      • Total spaces: 1
      • Parking features: Private, Storage, Workshop in Garage, Outside, Driveway
      • Garage spaces: 1
      • Has uncovered spaces: Yes
      Features
      • Levels: One and One Half
      • Stories: 1
      • Patio & porch: Enclosed, Front Porch, Patio, Screened, Side Porch, Terrace, Wrap Around
      • Exterior features: Other
      • Pool features: None
      • Fencing: None
      • Has view: Yes
      • View description: Trees/Woods
      Lot
      • Size: 1.7 Acres
      • Features: Irregular Lot, Secluded, Sloped, Sloped Up
      Details
      • Additional structures: Garage(s), Storage, Workshop
      • Parcel number: 515800274127
      • Zoning: R3
      • Zoning description: low-density residential district

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Wood Siding
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Fixer
      • New construction: No
      • Year built: 1970

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Electricity Available, Electricity Connected, Natural Gas Not Available, Phone Available, Sewer Not Available, Water Available, Water Connected

      Community & HOA

      Community
      • Security: Smoke Detector(s)
      Location
      • Region: Woodstock

      Financial & listing details

      • Price per square foot: $445/sqft
      • Tax assessed value: $290,800
      • Annual tax amount: $12,867
      • Date on market: 9/8/2026
      • Electric utility on property: Yes
      • Road surface type: Asphalt, Gravel

        Estimated market value

        $586,600

        $557,000 - $616,000

        $2,447/mo

        Price history

        DateEventPrice
        9/8/2026Listed for sale$595,000+83.1%$445/sqft
        Source: HVCRMLS #20265197 Report a problem
        10/3/2018Listing removed$325,000$243/sqft
        Source: BHHS HUDSON VALLEY PROP-WDST #20182636 Report a problem
        6/26/2018Listed for sale$325,000$243/sqft
        Source: Westwood Metes & Bounds - WH #20182636 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $250,000
        2024-- $250,000
        2023-- $250,000
        2022-- $250,000
        2021-- $250,000
        2020-- $250,000
        2019-- $250,000 +11.7%
        2018-- $223,900
        2017$6,649 $223,900
        2016-- $223,900
        2015-- $223,900
        2014-- $223,900
        2013-- $223,900
        2011-- $223,900
        2010-- $223,900
        2009-- $223,900
        2008-- $223,900
        2007-- $223,900
        2006-- $223,900
        2005-- $223,900
        2004-- $223,900 +88.8%
        2003-- $118,600
        2002-- $118,600
        2001-- $118,600
        2000-- $118,600
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 12498

        Getting around

        1 / 100
        Car-Dependent
        19 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Crosby K-4

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

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