104 North Garden Drive Pawling, NY $ 39,000,000
104 North Garden Drive
$ 39,000,000
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104 North Garden Drive

Pawling, NY, 12564
$ 39,000,000
Bedrooms9 Baths9.6 Sq 55,000

Monthly Estimate*

$ 243,309

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Single Family Home for sale in Pawling, NY

for $39,000,000 with 9 bedrooms and 9 full baths, 6 half baths. This 55,000 square foot home was built in 1987 on a lot size of 1337.

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.

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Single Family Active

Price

$ 39,000,000

Bedrooms

9

Full Bath

9

Half Bath

6

Property Type

Single Family

Taxes

$ 935,274

Style

Colonial,Contemporary,Estate

Lot Size

1337

Year Built

1987

Town/City

Pawling

County/Region

Dutchess

MLS | Web ID

936279

Features
Interior
Interior Amenities 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 Pr
Basement Finished
Flooring Hardwood Tile Wood
Total Fireplaces 20
Fireplace Features Bedroom Family Room Living Room Masonry
Basement Features Finished
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 6
Total Bedrooms 9
Total Baths 15
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General
Sewer Septic Tank
Heating Hot Air Oil Propane
Cooling Central Air
Utilities Underground Utilities
Appliances Dishwasher Dryer Gas Oven Gas Range Microwave Refrigerator Washer
Garage Spaces 3
Patio/Porch Features Deck Patio Porch Screened Terrace
Architectural Style Colonial Contemporary Estate
Pool Features Diving Board Electric Heat Indoor
Security Features Building Security Fire Alarm Fire Escape Security Gate Security Lights Video Cameras
Construction Materials Block Blown-In Insulation Brick Cedar Clapboard Frame Other Stone Wood Siding
Exclusions Ask LA
Year Built 1987
View Mountain(s) Panoramic Skyline Trees/Woods
Property Subtype Single Family Residence
Tax Year 2025
Waterfront Features Pond Waterfront
County Dutchess County
Property Type Residential
HOA N
Garage Y/N Y
Other Structures Barn(s) Guest House Outbuilding Pool House Residence Shed(s) Workshop
Total Rooms 58
Full Baths 9
High School Pawling High School
City Pawling
Senior Community Y/N N
High School District Pawling
Carport Y/N N
Elementary School Pawling Elementary School
Property Attached Y/N N
Tax Annual Amount 935274
Showing Instructions 48-72 hours notice please. Please email POF/Financial to amy.joanna@SothebysRealty.com. NDA must be signed prior to confirmation of showing by every party entering the property.
Middle/Junior High School Pawling Middle School
Property Condition Actual
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Pawling
Elementary School District Pawling
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Exterior
Exterior Amenities Courtyard Dock Fire Pit Juliet Balcony Lighting Tennis Court(s)
Fencing Partial
Parking Features Driveway Garage Driveway Garage
Water Source Well
Inclusions Ask LA
Foundation Details Other Block
Building Area Total 55000
Waterfront Y/N Y
Road Frontage Type County Road Private Road
Other Equipment Generator Pool Equip/Cover
Road Responsibility Public Maintained Road
Horse Y/N Y
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Internal Only
Street Number 1 104
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* Excluded Features
List By
Amy Smith Sroka

Listing Agent

Julia B Fee Sothebys Int. Rlty

Broker

amy.smith@juliabfee.com

Email

Affordability Calculator

$321,249
Per Month
76%
24%
0%
Monthly Principal & Interest
$243,309
Monthly Property Taxes
$77,940
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4100768 Elementary School
4099485 Middle School
Pawling High School High School
Pricing History
DatePricePrice ChangeDescription
12/24/2025$39,000,000 Listed Price

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104 North Garden Drive, Pawling, NY, 12564 is a Single Family Home for sale at $39,000,000 with 55,000 sqft and a lot size of 1337. 104 North Garden Drive has 9 bedrooms, 9.6 baths, and was built in 1987. The property's zip code is 12564 which is in Pawling, NY