Skip main navigation
For sale
  • $1,400,000

    4258 Route 44, Millbrook, NY 12545

    3beds
    10,689sqft
    Loading
    Single Family Residence, Residential
    Built in 1962
    1.9 Acres Lot
    $-- Zestimate®
    $131/sqft
    $-- HOA

    What's special

    Private three-bedroom apartmentStriking architectural detailsOutdoor gardensMultiple gathering areasSoaring ceilingsExpansive main levelHistoric character
    This distinctive property in the heart of Dutchess County combines historic character with over 10,000 square feet of versatile residential and commercial potential. Originally built in the 19th century as a Congregational church, the building has enjoyed a rich history and now offers endless possibilities for its next chapter. The expansive main level features multiple gathering areas, soaring ceilings, and striking architectural details that create a unique backdrop for a wide range of uses—whether hospitality, creative ventures, or professional space. Complementing the generous interior, outdoor gardens and landscaped grounds provide space for events or a serene setting for relaxation. Above the main level, a private three-bedroom apartment offers comfortable living with a deck overlooking the surrounding countryside. This rare combination of historic charm, substantial square footage, and adaptable layout makes the property ideal for a live/work arrangement, an investment opportunity, or a visionary redevelopment. With its rich character and flexible design, it presents a truly exceptional opportunity in one of the Hudson Valley’s most desirable locations.
    63 days
    |
    384
    |
    15
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    William Pitt Sothebys Int Rlty 203-644-1471,

    Stephen M. Pener 860-927-1141

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 996782MLS Logo

    Loading...

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 8
      • Full bathrooms: 4
      • 1/2 bathrooms: 4
      Heating
      • Oil
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Range, Refrigerator
      Features
      • High Ceilings
      • Basement: Unfinished
      • Attic: Finished,Partially Finished,Storage,Unfinished
      • Number of fireplaces: 3
      Interior area
      • Total structure area: 10,689
      • Total interior livable area: 10,689 sqft

      Property

      Parking
      • Parking features: Driveway, Off Street, Private
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Has view: Yes
      • View description: Mountain(s), Open
      Lot
      • Size: 1.9 Acres
      Details
      • Parcel number: 1358896966003334320000
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial,Other,Traditional
      • Property subtype: Single Family Residence, Residential
      • Attached to another structure: Yes
      Materials
      • Frame
      Condition
      • Year built: 1962

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Connected, Electricity Connected, Phone Connected

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Millbrook

      Financial & listing details

      • Price per square foot: $131/sqft
      • Tax assessed value: $906,400
      • Annual tax amount: $19,422
      • Date on market: 5/8/2026
      • Cumulative days on market: 44 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
        5/8/2026Listed for sale$1,400,000-3.4%$131/sqft
        Source: OneKey® MLS as distributed by MLS GRID #996782 Report a problem
        1/1/2026Listing removed$1,450,000$136/sqft
        Source: OneKey® MLS as distributed by MLS GRID #809427 Report a problem
        9/4/2025Price change$1,450,000-3.3%$136/sqft
        Source: OneKey® MLS as distributed by MLS GRID #809427 Report a problem
        1/3/2025Listed for sale$1,500,000$140/sqft
        Source: OneKey® MLS as distributed by MLS GRID #809427 Report a problem

        Public tax history

        Tax history is unavailable.

        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: 12545

        Getting around

        0 / 100
        Car-Dependent
        17 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Elm Drive Elementary School
        • Middle: Millbrook Middle School
        • High: Millbrook 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.

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes