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  • Price cut: $59K (11/6)
    $568,000

    42 Oakes Road, Highland, NY 12528

    5beds
    4,281sqft
    Loading
    Single Family Residence
    Built in 1800
    0.62 Acres Lot
    $562,000 Zestimate®
    $133/sqft
    $-- HOA

    What's special

    Original detailsViews are timelessThree-story homeSurrounded by beautiful gardensSubstantial lawnGenerously sized rooms
    Rarely do you find a property with such an up-close view of the Hudson River, offering a front-row seat to sailboats gliding by, tugboats slowly making their way along the water, and the romantic sound of the train. For generations, this home has stood watch over the Hudson, with a story that appears to reach back more than two centuries. While town records list the home as built in 1900, historical records associated with the property indicate its history may reach back to the early 1800s. Remarkably, the home has been continuously lived in through the generations. Set along the banks of the Hudson, beneath the Walkway Over the Hudson and Mid-Hudson Bridge, this three-story home is filled with character, with generously sized rooms, fireplaces, original details and a fourth floor tower offering a remarkable vantage point to watch life on the river go by. Surrounded by beautiful gardens and a substantial lawn, the property offers wonderful outdoor space overlooking the water, a setting that is increasingly hard to find. The home requires substantial renovation, but therein lies the opportunity: to thoughtfully restore its character, honor its history, and bring this Hudson River beauty back to its former glory. The work may be significant, but the setting is irreplaceable and the views are timeless. Franny Reese State Park is just minutes away for hiking and nature, while the train station, New Paltz, and Poughkeepsie are all within easy reach. For the buyer with vision, this is more than a renovation project. It is an opportunity to become part of the continuing story of a remarkable home in an extraordinary Hudson River setting.
    45 days
    18,025
    380

    Zillow last checked:

    Listing updated:

    Listed by:

    Corcoran Country Living 845-876-6676,

    Anne Rajs 845-797-1034

    Source: HVCRMLS,MLS#: 20265699MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 5
      • Full bathrooms: 5
      Heating
      • Propane, Zoned
      Appliances
      • Included: Washer, Refrigerator, Range, Microwave, Dryer, Dishwasher
      • Laundry: Laundry Room, Upper Level
      Features
      • Built-in Features, Eat-in Kitchen, High Ceilings
      • Flooring: Wood
      • Basement: Unfinished
      • Number of fireplaces: 1
      • Fireplace features: Metal
      Interior area
      • Total structure area: 4,281
      • Total interior livable area: 4,281 sqft
      • Finished area above ground: 4,281
      • Finished area below ground: 0

      Property

      Features
      • Stories: 3
      • Patio & porch: Deck
      • Exterior features: Garden, Private Yard
      • Has view: Yes
      • View description: Water
      • Has water view: Yes
      • Water view: Water
      • Body of water: Hudson River
      • Frontage type: River
      Lot
      • Size: 0.62 Acres
      • Features: Garden
      Details
      • Parcel number: 961
      • Zoning: R-2

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Other
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Stone
      Condition
      • Fixer
      • New construction: No
      • Year built: 1800

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Private Sewer
      • Water: Well
      • Utilities for property: Cable Connected, Electricity Available, Sewer Connected, Water Available

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Lloyd

      Financial & listing details

      • Price per square foot: $133/sqft
      • Tax assessed value: $329,000
      • Annual tax amount: $12,455
      • Date on market: 9/25/2026
      • Listing terms: Cash
      • Electric utility on property: Yes
      • Road surface type: Asphalt

        Estimated market value

        $562,000

        $534,000 - $590,000

        $7,003/mo

        Price history

        DateEventPrice
        11/6/2026Price change$568,000-9.4%$133/sqft
        Source: HVCRMLS #20265699 Report a problem
        10/19/2026Price change$627,000-3.4%$146/sqft
        Source: HVCRMLS #20265699 Report a problem
        9/24/2026Listed for sale$649,000+158.6%$152/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1054784 Report a problem
        12/6/2006Sold$251,000$59/sqft
        Source: HVCRMLS #20060376 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $329,000
        2024-- $329,000
        2023-- $329,000
        2022-- $329,000
        2021-- $329,000
        2020-- $329,000
        2019-- $329,000
        2018-- $329,000
        2017$10,981 $329,000
        2016-- $329,000
        2015-- $329,000
        2014-- $329,000
        2013-- $329,000
        2011-- $329,000 -6%
        2010-- $350,000 +40%
        2009-- $250,000
        2008-- $250,000
        2007-- $250,000
        2006-- $250,000 +27%
        2005-- $196,800
        2004-- $196,800
        2003-- $196,800 +19.9%
        2002-- $164,200
        2001-- $164,200
        2000-- $164,200
        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: 12528

        Getting around

        5 / 100
        Car-Dependent
        31 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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