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104 N Garden Drive

Pawling, NY 12564
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Bed 9

Bed

Bath 15

Bath

SqFt55,000

Sqft

SqFt1,337

Sqft(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $39,000,000

AD Id : 65334038

MLS Id : 936279

Beds : 9

Lot Size : 1,337 Sqft

Living Area Size : 55,000

Year Built : 1987

Garage : 3

County : Dutchess

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 9

    Bathroom Information

    Total Baths: 15 Full Baths: 9 Half Baths: 6

    Room Information

    Rooms Total: 58 Basement: Finished
  • Flooring Information

    Hardwood, Tile, Wood
  • Interior Features

    Built-in Features, Cathedral Ceiling(s), Eat-in Kitchen, Elevator, Entrance Foyer, High Ceilings, Kitchen Island, Natural Woodwork, Open Floorplan, Pantry, Recessed Lighting, Sauna, Storage, Tray Ceiling(s), Walk-In Closet(s) Appliances: Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, Washer
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Propane Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1987 Building Area Total: 55000 Construction Materials: Block, Blown-In Insulation, Brick, Cedar, Clapboard, Frame, Other, Stone, Wood Siding Patio And Porch Features: Deck, Patio, Porch, Screened, Terrace Pool Features: Diving Board, Electric Heat, Indoor, Private Private Pool: Yes Water front Features: Pond, Waterfront, Waterfront Access View: Mountain(s), Panoramic, Skyline, Trees/Woods
  • Exterior Features

    Exterior Features: Courtyard, Dock, Fire Pit, Lighting, Tennis Court(s)

  • Lot Information

    Lot Size Acres: 1337 Lot Size Square Feet: 58239000 Lot Description: Waterfront, Near Golf Course, Private, Secluded, Wooded

  • Listing Price Information

    Listing Price: $39000000

  • Tax Information

    Parcel Number: 134089-7057-00-977709-0000 Annual Tax: $935274

  • Parking Information

    Driveway, Garage

    Garage Information

    Has Garage: Yes Garage Space: 3

  • School Information

    Elementary School: Pawling Elementary School
    Junior High School: Pawling Middle School
    Senior High School: Pawling High School
  • Utility Information

    Underground Utilities
  • Location Information

    WaterSource: Private, Well Security Features: Building Security, Fire Alarm, Fire Escape, Security Gate, Security Lights
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
41 AND 43 Meeting House.., Pawling, NY, 12564 $1,799,000 5 6 5,390 5,390 SqFt
34 Meeting House Road, Pawling, NY, 12564 $2,500,000 3 4 2,292 2,292 SqFt
15 Kirby Hill Road, Pawling, NY, 12564 $14,995,000 4 4 3,942 3,942 SqFt
809 Quaker Hill Road, Pawling, NY, 12564 $3,100,000 3 3 3,600 3,600 SqFt
618 Quaker Hill Road, Pawling, NY, 12564 $5,000,000 8 13 15,000 15,000 SqFt
1141 Old Quaker Hill Road, Pawling, NY, 12564 $499,999 2 1 1,347 1,347 SqFt
64 S Quaker Hill Road, Pawling, NY, 12564 $1,300,000 5 4 4,248 4,248 SqFt
57 Buhleir Road, Pawling, NY, 12564 $629,900 3 2 1,768 1,768 SqFt
188 N Quaker Hill Road, Pawling, NY, 12564 $595,000 3 3 2,636 2,636 SqFt
7 Holm Run, Pawling, NY, 12564 $495,000 3 2 1,172 1,172 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 06/17/2026 @ 08:14

MLS: 936279 LISTED BY: Amy Sroka, Julia B Fee Sothebys Int. Rlty 914-234-0200 SOURCE: OneKey MLS

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