104 North Garden Drive, Pawling, NY 12564

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Property Description

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. Compr

104 North Garden Drive | MLS# 936279

This single family home located at 104 North Garden Drive, Pawling, NY 12564 is currently listed for sale with an asking price of $39,000,000. This property was built in 1987 and has 9 bedrooms and 9 full and 6 partial baths with 55000 sq. ft. North Garden Drive is located within the Pawling school district. Search Pawling real estate on www.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Finished
Cooling: Central Air
Fireplaces: 20
Garage: 3
Heating: Hot Air, Oil, Propane
Home Style: Colonial, Contemporary, Estate
Lot Size: 1,337.00 Acres
Taxes: $935,274
Year Built: 1987

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
Primary Bathroom
Recessed Lighting
Sauna
Storage
Tray Ceiling(s)
Walk-In Closet(s)
Courtyard
Dock
Fire Pit
Juliet Balcony
Lighting
Tennis Court(s)

Feature Descriptions

Appliances: Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, Washer
Attic: Dormer
Building Area Total: 55000
Days on Site: 70
Elevator: Y
Exclusions: Ask LA
Exterior: Block, Blown-In Insulation, Brick, Cedar, Clapboard, Fr
Fencing: Partial
Fireplace Features: Bedroom, Family Room, Living Room, Masonry
Fireplace Y/N: Yes
Flooring: Hardwood, Tile, Wood
Formal Dining: Yes
GarageY/N: Yes
HorseY/N: Yes
Inclusions: Ask LA
Lot Features: Near Golf Course, Near School, Near Shops, Part Wooded, Private, Secluded, Wooded
Number Of Kitchens: 1
On Market Date: 2025-12-24
Other Structures: Barn(s), Guest House, Outbuilding, Pool House, Residence, Shed(s), Workshop
Parking Features: Driveway, Garage
Patio And Porch: Deck, Patio, Porch, Screened, Terrace
Pool Features: Diving Board, Electric Heat, Indoor
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Rooms Total: 58
Sauna: Yes
Security Features: Building Security, Fire Alarm, Fire Escape, Security Gate, Security Lights, Video Cameras
Sewer: Septic Tank
Special View Info: Mountain(s), Panoramic, Skyline, Trees/Woods
Swimming Pool: Yes
Utilities: Underground Utilities
Water: Well
Waterfront Features: Pond, Waterfront
Wooded: Yes

Local Schools

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

Estimate Your Payment

Estimated Payment

$ 176,111.59 per month $86,797.09 Principal & Interest $77,939.50 Property Tax $11,375.00 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Julia B Fee Sothebys Int. Rlty
Agency Phone: 914-234-0200

Shown By

Agency Title: Timberland Properties
Agency Phone: 845-586-3321

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