104 N Garden Drive | Pawling

$39,000,000 | 9 Beds | 15 Baths (9 Full, 6 Half) | 55,000 Sq. Ft.

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.\nNestled in the heart of nature, this extraordinary private estate spans nearly 1,338 acres, offering unparalleled seclusion, natural beauty, and world-class amenities.\nDesigned 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.\nThe 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.\n 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.\nThis 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.\nComplementing 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.\nAnchoring 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.\nBeyond 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. OneKeyMLS 936279

MLS Listing ID: 
OneKeyMLS 936279
Community Information
School District: 
Pawling Central
Building Details
Details about the building on a property.
Architectural Style: 
Colonial,Contemporary,Estate
Year Built: 
1987
Living Area: 
55,000
Basement: 
Finished
Interior: 
Built-in Features,Cathedral Ceiling(s),Chefs Kitchen,Eat-in Kitchen,Elevator,Entertainment Cabinets,Entrance Foyer,Formal Dining,High Ceilings,Kitchen Island,Natural Woodwork,Open Floorplan,Pantry,Primary Bathroom,Recessed Lighting,Sauna,Storage,Tray Ceil
Fireplaces: 
Bedroom,Family Room,Livin
Construction
Construction Materials: 
Block,Blown-In Insulation,Brick,Cedar,Clapboard,Frame,Other,Stone,Wood Siding
Exterior Features: 
Courtyard,Dock,Fire Pit,Juliet Balcony,Lighting,Tennis Court(s)
Room Details
Details about the rooms in the building.
Total Rooms: 
58
Total Bedrooms: 
9
Total Bathrooms: 
15
Total Full-Bathrooms: 
9
Total Half-Bathrooms: 
6
Utilities
Information about utilities available on the property.
Heating System: 
Hot Air,Oil,Propane
Cooling System: 
Central Air
Water Source: 
Well
Sewer: 
Septic Tank
Lot/Land Details
Details about the lots and land features included on the property.
View: 
Mountain(s),Panoramic,Skyline,Trees/Woods
Waterfront: 
1
Water Body Category: 
Pond,Waterfront
Lot Features
Parking Type: 
Driveway,Garage
Fence: 
Partial
Public Record
Parcel Number: 
134089-7057-00-977709-0000
Annual Tax: 
$935,274.00
Listing Dates
Dates involved in the transaction.
Listing Entry Date/Time: 
12/24/2025
Contract Details
Details about the listing contract.
Exclusions: 
Ask LA
Listing Participants
Participants (agents, offices, etc.) in the transaction.
Listing Agent Name: 
Amy Smith Sroka
Listing Co-Agent Name: 
Joanna Rizoulis
Listing Office Name: 
Julia B Fee Sothebys Int. Rlty
Listing Co-Office Name: 
Julia B Fee Sothebys Int. Rlty