104 North Garden Drive, Pawling, NY

$39,000,000

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9

Beds

15

Baths

55,000

Square feet

1337.00

Acres

About 104 North Garden Drive

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.

Features of 104 North Garden Drive

MLS® # 936279
Price $39,000,000
Bedrooms 9
Bathrooms 15.00
Full Baths 9
Half Baths 6
Square Footage 55,000
Acres 1,337.00
Taxes $935,274
Year Built 1987
Type Residential
Sub-Type Single Family Residence
Style Colonial, Contemporary, Estate
Status Active

Community Information

Address 104 North Garden Drive
City Pawling
County Dutchess County
State NY
Zip Code 12564
Adult 55+ Community No

Amenities

Utilities Underground Utilities
Parking Driveway, Garage
# of Garages 3
View Mountain(s), Panoramic, Skyline, Trees/Woods
Is Waterfront Yes
Waterfront Pond, Waterfront
Has Pool Yes
Pool Diving Board, Electric Heat, Indoor

Interior

Interior Hardwood, Tile, Wood
Interior Features 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 Ceiling(s), Walk-In Closet(s)
Appliances Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, Washer
Heating Hot Air, Oil, Propane
Cooling Central Air
Has Basement Yes
Basement Finished
Fireplace Yes
# of Fireplaces 20
Fireplaces Bedroom, Family Room, Living Room, Masonry

Exterior

Exterior Features Courtyard, Dock, Fire Pit, Juliet Balcony, Lighting, Tennis Court(s)
Lot Description Near Golf Course, Near School, Near Shops, Part Wooded, Private, Secluded, Wooded
Exterior Block, Blown-In Insulation, Brick, Cedar, Clapboard, Frame, Other, Stone, Wood Siding

School Information

District Pawling
Elementary Pawling Elementary School
Middle Pawling Middle School
High Pawling High School

Additional Information

Date Listed December 24th, 2025
Days on Market 49
Short Sale No
RE / Bank Owned No

Listing Details

OfficeJulia B Fee Sothebys Int. Rlty

Listing Map

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