104 North Garden Drive Pawling NY, 12564

Property Type: | Property Features:

Property Details

Price: $39,000,000

Year Built: -

Floors: -

Bedrooms: 9

Bathrooms: 15

Location Info

Address: 104 North Garden Drive

City: Pawling

State: NY

Zip: 12564

Country: USA

MLS #: MLSⓇ ID 936279

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Property Description

Est. payment: $285,514/mo

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 family 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 family 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 Japanese 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.

Location

104 North Garden Drive Pawling NY, 12564

Interior Features

Bedrooms	9
Total Bathrooms	15
Full Bathrooms	9
Half Bathrooms	6
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
Floor Description	Hardwood, Tile, Wood
Fireplace	Yes
Fireplace Description	Bedroom, Family Room, Living Room, Masonry
Cooling	Yes
Cooling Description	Central Air
Heating	Yes
Heating Description	Hot Air, Oil, Propane
Basement	Yes

Exterior Features

Lot Size	1,336.98 Acres
Exterior Features	Courtyard, Dock, Fire Pit, Juliet Balcony, Lighting, Tennis Court(s)
Lot Features	Near Golf Course, Near School, Near Shops, Part Wooded, Private, Secluded, Wooded
Architectural Style	Colonial, Contemporary, Estate
Sewer	Septic Tank
Patio and Porch	Deck, Patio, Porch, Screened, Terrace
Security	Building Security, Fire Alarm, Fire Escape, Security Gate, Security Lights, Video Cameras

School Information

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

Other Property Details

Taxes	$935,274
Tax Frequency	Annually
Days on Market	1
Garage	Yes
Garage Spaces	3
Parking	Driveway, Garage
View	Yes
View Description	Mountain(s), Panoramic, Skyline, Trees/Woods
County	Dutchess County
Water Source	Well
Pool	Yes
Pool Features	Diving Board, Electric Heat, Indoor
Waterfront	Yes
Waterfront Features	Pond, Waterfront
Utilities	Underground Utilities
55+/Senior Community	No

Listed by Amy Smith Sroka Joanna Rizoulis with Julia B Fee Sothebys Int. Rlty
Listing Contact: (914) 523-0678

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor At Home with Yara Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS

Data last updated 3:11 AM UTC, 12/26/2025