• 104 North Garden Drive, Pawling, NY, 12564

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    $39,000,000
    71 Days On Site

    104 North Garden Drive
    Pawling, NY 12564

    For Sale|Single Family Residence|Active
    9
    Beds
    15
    Total Baths
    9
    Full Baths
    6
    Partial Baths
    55,000
    SqFt
    $709
    /SqFt
    1987
    Built
    County:
    Dutchess
    Listing courtesy of Julia B Fee Sothebys Int. Rlty amy.smith@juliabfee.com
    Call Now: 845-791-5945
    Is this the listing for you? We can help make it yours.
    845-791-5945
    104 North Garden Drive104 North Garden Drive104 North Garden Drive104 North Garden Drive
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    Mortgage Calculator

    Monthly Payment (Est.)

    $177,934
    Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

    Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it is a once-in-a-lifetime opportunity. Nestled in the heart of nature, this extraordinary private estate spans nearly 1,338 acres, offering unparalleled seclusion, natural beauty, and world-class amenities. Designed as a one-of-a-kind sanctuary, the retreat spans 23 tax lots and showcases breathtaking landscapes, luxurious accommodations, and distinctive architectural elements that blend seamlessly with the surrounding environment. The estate is best described with three large property zones. The Garden Parcel, with 17 lots and seven residences, totaling 751.51 acres, forms the centerpiece of the property. Purgatory Hill encompasses three lots and three residences across 337.61 acres. The Northwest Territory offers 248.63 acres of unspoiled vacant land across three lots. Together, these parcels create an estate of remarkable scale and diversity. balancing residential, recreational, and natural elements. At the heart of the Garden Parcel rises the 55,000-square-foot main residence-an architectural masterpiece surrounded by six additional homes. Within its walls are nine bedrooms, nine full baths, six half baths, and twenty fireplaces, each space crafted with extraordinary attention to detail. The grounds embrace the spirit of the Appalachian Trail, with native plantings and curated landscapes creating a harmonious environment. This grand residence is as functional as it is breathtaking. Designed for both everyday living and exceptional entertaining, it features an indoor pool and spa framed by the surrounding natural landscape, expansive gathering spaces, and an indoor basketball court complete with locker rooms. Two secure, climate-controlled art storage areas further reflect the home's thoughtful design and attention to detail. Complementing the main residence, the Garden Parcel also features a meticulously maintained 6,000-square-foot guest house with its own pool. Artfully designed, the Tea House further enhances the parcel, offering a peaceful space for both reflection and intimate gatherings. Over 20 miles of interior roads and trails wind through the landscape, inviting exploration by foot, bike, or vehicle. Comprehensive maps detail the extensive network of roads, streams, ponds, and structures. Anchoring the operational side of the estate, the Office Complex features a four-bay machine barn with a lift and wash pad, a multilevel office building, and a dedicated security outpost. This infrastructure ensures seamless management of the property's extensive resources. Beyond its natural beauty, this estate embodies versatility, solitude, and enduring grace – a true legacy property unlike any other in the Hudson Valley. Thoughtfully curated down to its meticulously appointed landscape, Woodland Waters now awaits its next steward to cherish and preserve for generations to come.

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    Listing Snapshot
    Price 
    $39,000,000
    Days On Site 
    71 Days
    Bedrooms 
    9
    Inside Area (SqFt) 
    55,000 sqft
    Total Baths 
    15
    Full Baths 
    9
    Partial Baths 
    6
    Lot Size 
    1,337 Acres
    Year Built 
    1987
    MLS® Number 
    936279
    Status 
    Active
    Property Tax 
    $935,274
    HOA/Condo/Coop Fees 
    N/A
    Sq Ft Source 
    N/A
    Friends & Family
    Recent Activity
    2 months agoListing first seen on site
    2 months agoListing updated with changes from the MLS®
    General Features
    Acres 
    1337
    Garage 
    Yes
    Garage Spaces 
    3
    Parking 
    DrivewayGarage
    Property Sub Type 
    Single Family Residence
    Security 
    Building SecurityFire AlarmFire EscapeSecurity GateSecurity Lights
    Sewer 
    Septic Tank
    SqFt Total 
    55000
    Style 
    ColonialContemporaryEstate
    Utilities 
    Underground Utilities
    Water Source 
    PrivateWell
    Interior Features
    Appliances 
    DishwasherDryerGas OvenGas RangeMicrowaveRefrigeratorWasher
    Basement 
    Finished
    Cooling 
    Central Air
    Fireplace 
    Yes
    Fireplace Features 
    BedroomFamily RoomLiving RoomMasonry
    Fireplaces 
    20
    Flooring 
    HardwoodTileWood
    Heating 
    OilPropane
    Interior 
    Built-in FeaturesCathedral Ceiling(s)Eat-in KitchenElevatorEntrance FoyerHigh CeilingsKitchen IslandNatural WoodworkOpen FloorplanPantryRecessed LightingSaunaStorageTray Ceiling(s)Walk-In Closet(s)
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    Exterior Features
    Construction Details 
    BlockBlown-In InsulationBrickCedarClapboardFrameOtherStoneWood Siding
    Exterior 
    CourtyardDockFire PitLightingTennis Court(s)
    Fencing 
    Partial
    Lot Features 
    WaterfrontNear Golf CoursePrivateSecludedWooded
    Other Structures 
    Barn(s)Guest HouseOutbuildingPool HouseResidenceShed(s)Workshop
    Patio And Porch 
    DeckPatioPorchScreenedTerrace
    Pool Features 
    Diving BoardElectric HeatIndoorPrivate
    Private Pool 
    Yes
    Road Frontage 
    County RoadPrivate Road
    View 
    Mountain(s)PanoramicSkylineTrees/Woods
    Waterfront Features 
    PondWaterfrontWaterfront Access
    Waterview 
    Mountain(s)PanoramicSkylineTrees/Woods
    Community Features
    Horse Allowed 
    Yes
    School District 
    Pawling
    Schools
    School District
    Pawling
    Elementary School
    Pawling Elementary School
    Middle School
    Pawling Middle School
    High School
    Pawling High School
    Listing courtesy of Julia B Fee Sothebys Int. Rlty amy.smith@juliabfee.com


    Based on information submitted to the MLS GRID as of 2026-03-05 07:32 PM EST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

    Neighborhood & Commute
    Source: Walkscore
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