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For sale
  • Price cut: $200K (7/10)
    $999,999

    39 N Chestnut Street, New Paltz, NY 12561

    9beds
    3,273sqft
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    Triplex, Multi Family
    Built in 1890
    -- sqft lot
    $-- Zestimate®
    $306/sqft
    $-- HOA

    What's special

    Detached garage
    Charming 1890 brick Victorian triplex in the heart of the Village of New Paltz. Located at 39 N Chestnut St, this well-maintained multi-family property offers a rare opportunity for both owner-occupants and investors seeking strong, consistent rental income in one of the Hudson Valley’s most sought-after and high-demand village locations. It also presents a unique tri-family getaway opportunity, ideal for extended family use, multi-generational living, or a shared Hudson Valley retreat with income potential. The location is truly exceptional - set in the vibrant village core where everything is just steps away. Enjoy immediate access to SUNY New Paltz, local cafes, restaurants, shops, and daily conveniences, along with direct proximity to the Rail Trail for recreation and an easy connection to the broader Hudson Valley lifestyle. The Trailways bus station is also nearby, providing direct and convenient access to New York City for commuters and visitors alike. The property features a total of 3,273 square feet with three separate units. The first floor consists of a spacious 2-bedroom apartment with an additional flex room that generates $3,300/month. The second-floor unit is a 3-bedroom apartment with a monthly rental income of $2,625. The third-floor unit is a 4-bedroom apartment generating $3,000/month. Total monthly rental income is $8,925, equating to $107,100 annually. Recent improvements include a new roof installed in 2025. Tenants are responsible for their own heat and electric, helping to minimize owner expenses. The property offers off-street parking at the rear, along with a detached garage. A rare opportunity to own a character-filled 1890 brick Victorian multi-family property in a premier Village of New Paltz location - offering strong income, long-term upside, and unmatched walkability in a consistently in-demand rental market.
    54 days
    |
    568
    |
    25
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    eXp Realty 888-276-0630,

    Jacob M. Cohen 845-514-7786

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1000543MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 9
      • Bathrooms: 4
      • Full bathrooms: 4
      Heating
      • Forced Air
      Cooling
      • None
      Features
      • First Floor Bedroom, First Floor Full Bath, Natural Woodwork
      • Basement: Full,Unfinished,Walk-Out Access
      • Attic: None
      • Has fireplace: No
      Interior area
      • Total structure area: 3,273
      • Total interior livable area: 3,273 sqft

      Property

      Parking
      • Total spaces: 1
      • Parking features: Driveway, Garage, Parking Lot
      • Garage spaces: 1
      • Has uncovered spaces: Yes
      Features
      • Exterior features: Courtyard
      Lot
      • Size: 6,534 Square Feet
      • Features: Near Golf Course, Near Public Transit, Near School, Near Shops
      Details
      • Parcel number: 3801086.0340001009.1000000
      • Special conditions: None

      Construction

      Type & style
      • Home type: MultiFamily
      • Architectural style: Victorian
      • Property subtype: Triplex, Multi Family
      Materials
      • Brick
      Condition
      • Year built: 1890

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected

      Community & HOA

      Location
      • Region: New Paltz

      Financial & listing details

      • Price per square foot: $306/sqft
      • Tax assessed value: $380,000
      • Annual tax amount: $8,592
      • Date on market: 5/20/2026
      • Cumulative days on market: 55 days
      • Listing agreement: Exclusive Right To Sell
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/10/2026Price change$999,999-16.7%$306/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1000543 Report a problem
        5/20/2026Listed for sale$1,199,999$367/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1000543 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024-- $380,000
        2023-- $380,000
        2022-- $380,000
        2021-- $380,000
        2020-- $380,000
        2019-- $380,000
        2018-- $380,000
        2017$11,839 $380,000
        2016-- $380,000
        2015-- $380,000 -15.4%
        2014-- $449,000
        2013-- $449,000
        2011-- $449,000
        2010-- $449,000 +5.6%
        2009-- $425,000
        2008-- $425,000
        2007-- $425,000 +26.9%
        2006-- $335,000
        2005-- $335,000 +9.8%
        2004-- $305,000 +13.8%
        2003-- $268,000 +34%
        2002-- $200,000 +18.3%
        2001-- $169,000
        2000-- $169,000
        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 12561

        Getting around

        84 / 100
        Very Walkable
        58 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Duzine
        • Middle: New Paltz Middle School
        • High: New Paltz Senior High School

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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