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.
- Heating System:
- Oil, Propane, Hot Air
- Cooling System:
- Central Air
- Basement:
- Finished
- View:
- Mountain(s), Panoramic, Skyline, Trees/woods
- Fence:
- Partial
- Patio:
- Patio, Porch, Screened, Deck, Terrace
- Swimming Pool:
- Indoor, Electric Heat, Diving Board
- Appliances:
- Dishwasher, Refrigerator, Microwave, Dryer, Washer, Gas Range, Gas Oven
- Exterior Features:
- Dock, Tennis Court(s), Courtyard, Juliet Balcony, Lighting, Fire Pit
- Fireplace Features:
- Bedroom, Family Room, Living Room, Masonry
- Fireplaces Total:
- 20
- Flooring:
- Hardwood, Tile, Wood
- Garage Spaces:
- 3
- Interior Features:
- Eat-in Kitchen, Elevator, Entrance Foyer, Open Floorplan, High Ceilings, Cathedral Ceiling(s), Pantry, Storage, Sauna, Walk-in Closet(s), Chefs Kitchen, Kitchen Island, Formal Dining, Primary Bathroom, Entertainment Cabinets, Built-in Features, Recessed Lighting, Natural Woodwork, Tray Ceiling(s)
- Lot Features:
- Wooded, Private, Secluded, Part Wooded, Near Shops, Near School, Near Golf Course
- Parking Features:
- Driveway, Garage
- Sewer:
- Septic Tank
- Utilities:
- Underground Utilities
- City:
- Pawling
- State:
- NY
- Street:
- Garden
- Street Number:
- 104
- Street Suffix:
- Drive
- Postal Code:
- 12564
- Floor Number:
- 0
- Longitude:
- W74° 25' 51''
- Latitude:
- N41° 34' 44.4''
- PostalCity:
- Pawling
- Street Dir Prefix:
- N
- Architectural Style:
- Colonial, Contemporary, Estate
- Construction Materials:
- Brick, Frame, Wood Siding, Other, Stone, Block, Blown-in Insulation, Cedar, Clapboard
- Elementary School:
- Pawling Elementary School
- High School:
- Pawling High School
- Agent MlsId:
- 4483
- MiddleOrJunior School:
- Pawling Middle School
- PhotosCount:
- 46
- Special Listing Conditions:
- No
- Tax Annual Amount:
- $935,274
- Water Source:
- Well
- Office MlsId:
- JBFSOT07
Residential - MLS# 936279
104 Garden Drive, Pawling, NY
- Property Type :
- Residential
- Property SubType :
- Single Family Residence
- Listing Type :
- For Rent
- Listing ID :
- 936279
- Price :
- $39,000,000
- Rooms :
- 58
- Bedrooms :
- 9
- Bathrooms :
- 9
- Half Bathrooms :
- 6
- Bathrooms Total :
- 15
- Square Footage :
- 55,000 Sqft
- Building Area :
- 55,000 Sqft
- Lot Area :
- 1,337 Acre
- Year Built :
- 1987
- Status :
- Active
- Listing Agent :
- Amy Smith Sroka
- Listing Office :
- Julia B Fee Sothebys Int. Rlty















































