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    (845) 398-1717 susan@ImagineProperties1.com
    • 100 Dutch Hill Rd Suite 260
      Orangeburg, NY 10962
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    Home / Monticello / 399 Gregory Road
    399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 399 Gregory Road Monticello, NY 12701 View All Photos

    $5,000,000

    | Active

    399 Gregory Road

    Monticello, NY 12701

    17,570
    Square Feet
    14
    Beds
    14.5
    Baths
    20.00
    Acres
    145
    Days on Market
    KEY976893
    MLS#
    House
    Structure
    Residential
    Zone
    Contact

    399 Gregory Rd, Monticello, NY – A Private Estate Like No Other Set on 20 breathtaking acres in Monticello, this extraordinary nearly 18,000sf gated estate delivers an unmatched combination of scale, luxury, and privacy. Surrounded by a perfect blend of open land and natural beauty—including a picturesque stream and sweeping views—this property offers a rare sense of seclusion just minutes from the area’s top destinations. Ideally located near Monticello Motor Club, Resorts World Catskills, Kartrite Indoor Water Park, Monster Golf Course, Bethel Woods Center for the Arts, and the scenic Catskill Mountains, this estate combines tranquility with convenience and access to year-round attractions. Inside, the home is designed for both grand entertaining and everyday comfort. Amenities include a spectacular indoor pool, full bar, pizza oven, game room, private theater, gym, multiple fireplaces, sauna, and hot tub—creating a true resort-style experience. With 14+ bedrooms, this property has successfully hosted weddings, retreats, and large gatherings. Nearly every aspect of the home has been thoughtfully upgraded by the current owners. Improvements include a brand new dehumidifier and heater for the indoor pool, new heating and cooling systems, upgraded electric, low-voltage wiring, security cameras, and a brand-new high-capacity septic system. The estate also offers a fully equipped kitchen, a fully equipped game room, a detached garage, and a separate, private suite on the upper level. The entire property is fully winterized and move-in ready. Zoned RR2, this estate presents exceptional flexibility and investment potential. With planning board approval, it is well-suited for use as a retreat center, summer camp, or event venue. A discerning buyer can enjoy this home as a private luxury escape while also generating substantial income through rentals, weddings, and organizational use throughout the year. This is truly a property that must be experienced in person to fully appreciate the scale, craftsmanship, and atmosphere it offers—photos simply don’t capture the full picture of what this mansion entails. A rare opportunity for the buyer who values privacy, prestige, and potential—this is more than a home, it’s a legacy estate. Reach out today to schedule your private tour.

    Property Details
    Interior
    Chandelier, Entrance Foyer, Granite Counters, High Ceilings, High Speed Internet, Primary Bathroom, Open Kitchen, Sound System,
    Fireplaces
    2
    Cooling
    Central Air
    Heating
    Forced Air
    Cooling Features
    Central Air
    Bedrooms
    14
    Bathrooms
    14.5
    Full Baths
    12
    Half Baths
    5
    View
    Trees/Woods
    Lot Features
    Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
    Lot Description
    Back Yard, Front Yard, Landscaped, Part Wooded, Private, Views, Wooded
    Pool
    1
    Pool Description
    In Ground, Indoor
    Pool Features
    In Ground, Indoor
    Exterior Materials
    Fire Pit, Gas Grill, Lighting, Mailbox, Playground
    Acres
    20.0
    Square Feet
    17570.0
    Parking Features
    Covered, Driveway, Garage, Parking Lot
    Parking
    1
    Parking Spaces
    20.0
    Parking Type
    Driveway
    Parking Garage
    1
    Parking Garage Spaces
    2.0
    Property Type
    Purchase
    Basement
    1
    Basement Description
    Partial, Storage Space, Unfinished
    Basement Finished
    1
    Year Built
    1989
    Foundation
    Concrete Perimeter
    Sewer Information
    Septic Tank
    Utility Source
    Well
    Utility Features
    Electricity Connected
    Appliances
    Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Oven, Oven, Refrigerator, Washer, Tankless Water Heater
    School District
    Monticello
    Elementary School
    George L Cooke School
    Middle School
    Robert J Kaiser Middle School
    High School
    Monticello High School
    County
    Sullivan County
    Region
    Thompson
    Original List Price
    $5,000,000
    Days on Market (Cumulative)
    145
    Taxes Annual
    $31,248
    MLS #
    976893
    Location
    Legal

    IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

    Provided By
    Listed by Rivky Klagsbrun (#KEY347038)
    Listing Office: Catskills Home Services (#KEYCATKLS)

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